
Bennington and the surrounding area offer a plethora of opportunities for outdoor adventures. State parks, mountain lakes, swimming holes, and hikes for all ages and abilities abound. Bennington is nestled into the southwest corner of the Green Mountains and is a favorite stopping point along the Appalachian and Long Trails. For the casual walker there is no shortage of beautiful scenic walks with pastoral views and historic sites.
The town also offers numerous parks including a splash pad, disc golf, tennis, playgrounds, and an impressive recreation center complex with indoor pool and weight room.
When temperatures drop, some of the best cross-country skiing and snow shoeing in the Northeast has brought the U.S. National Snowshoe competition to Prospect Mountain twice in the past five years. The V.A.S.T. snowmobile trail network draws visitors from all over New England.
Breathtaking mountain views abound from every hole on our 18-hole championship golf course. For rainy day activities, Bennington has indoor golf simulator, a tennis bubble, bowling alley and more.
There are a good number of annual events related to the outdoors, and an active community of outdoor recreation loving organizations that invite participation in their activities and efforts.
Whatever your passion, Bennington’s numerous outdoor opportunities will not disappoint you!
Related Links:
- Hiker / Biker Information Crib Sheet for Bennington (updated August 2022)
- Bennington Trailfest
Pickett Hill Guide Service
Located at the foothills of the Green Mountain National Forest in Bennington, Vermont. Pickett Hill Guide Service is here to bring you closer to nature. Whether you are a seasoned hunter or have not once stepped foot into the woods, we promise to provide you with a unique and enriching experience.
(802) 442-2317
VAST
(snowmobiles and ATVs)
Founded 50 years ago, Vermont Association of Snow Travelers (VAST) is responsible for the organization of the sport of snowmobiling, maintaining and grooming over 4,700 miles of trails in Vermont. One of the oldest snowmobiling organizations in the U.S., VAST is a non-profit 501-c-3 organization that includes 127 clubs statewide, with over 24,000 members combined. The clubs and their steadfast volunteers, and the landowners that allow riders to cross their land are the backbone of the organization.
Western New England Greenway
(Biking, roadways)
A bike route that runs along US Route 7, including through Bennington and beyond.

(Trail, hiking, walking, swimming)
The Upper Tubs waterfall is a popular swimming hole for locals that can be reached after an easy hike through the Pownal woodland.
This is a “leave no trace” area… please be sure to pack out all trash.

(hiking trails and maps)
AllTrails.com
Trailfinder.info
Green Mountain Club
HQ webpage has blogs / hike suggestions.
Green Mountain National Forest
See maps, elevation information, up to date weather, and reviews for local trails.
Return to Recreational Opportunities in Bennington and the Region
An Essential Guide to Enjoying National Parks

(Skiing, snowboarding, alpine slide, waterslide, aerial adventure park)
Nine lifts carry guests to trails covering 178 of the 300 acres on Bromley Mountain. Lessons and rentals are available.
3984 VT Route 11
Peru, VT

(Hiking, walking, trails)
The Robert Frost Trail extends two miles from Lake Paran in North Bennington to Route 7A in Shaftsbury. Easy packed dirt trails, pets permitted on leash.
Accessible from either Lake Paran in North Bennington or at the trailhead just south of the Robert Frost Stone House on Route 7A in Shaftsbury.
Bennington Trail Cruisers
(Summer/Fall, ATVs)
The Bennington Trail Cruisers want YOU!! We are a group of responsible and highly experienced ATV riders that promote safe and legal ATV riding. As a member of the B.T.C. we assure trails are safe, clean, and environmentally friendly.
(518) 892-4719

Looking for an escape from the pressures of everyday life? GO FISHING! It’s a close-to-home, stress-relieving getaway and a great way to reconnect with family and friends. Check out all Vermont has to offer for a dose of good old fashioned fun.
Y Woods
(Trails, biking, hiking)
Accessible from Strohmaier Rd in Bennington
Bennington Trail Map
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Stark Street Playground
(Playground, bike pump track, basketball hoop)
This park is currently under construction to update the facilities and offer more recreational opportunities.
150 Stark St.
Bennington, VT 05201
https://benningtonvt.org/departments/parks-recreation/
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BATS (Bennington Area Trail System)
(Biking, hiking, trail maintenance)
BATS was founded by a group of local bikers, runners, and hikers that advocate for multi-use singletrack trails for the enjoyment of area residents and visitors alike.
batsvt.org

Greenbergs Headwaters Park
(Nature, bird watching, trails)
Belvidere Street
(off of Morgan Street)
Bennington, VT

It features two miles of paths that access a diversity of habitats ranging from wooded uplands to ponds and beaverdams. The South Stream feeds into the wetland which is rated as a Vermont Class 2 Significant Wetland.
Part of the trail system is on the rail bed of the former Bennington and North Adams railway (service ended in 1928). At one time, the trolley line which belonged to the Bennington and Hoosick Valley Railway west of Bennington, ran to Hoosick Falls, NY, a total of about 30 miles.
There is a second entrance to the park for paddlers, located farther down Morgan Street, just past the turn off to Middle Pownal Road. There is a long boardwalk leading to the canoe/kayak launch that takes you directly into the heart of the beaver ponds and wetlands area.
Enjoy walking, paddling, bird watching, cross country skiing, mountain biking, and all the park has to offer!
Birdwatching at the Headwaters Park:
eBird.org

Riverwalk
(Walking, downtown)
An easy walk down the Walloomsac in Bennington. Less than a mile from Depot St to Park St.
Riverwalk map
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A Re-design and Replacement of the Playgrounds
The iconic playgrounds at Willow Park that have been a beloved feature for decades are now being entirely rebuilt with new accessible and inclusive play structures that the community has helped choose.
One thing that will not change… the engraved bricks honoring the donors who built the original park will be preserved.
Work on the Installation of the New Playgrounds Has Begun
A work crew from Childscapes (the sub contractor doing the demolition and installation of the new playground) arrived on July 26, 2022, and started demolition work of the small playground by the upper pavilion. The new playground equipment was delivered and demolition on the large playground began on July 27. The sub-contractor doing the site work and setup is Childscapes.
The work should take a month or so. We will provide regular updates, and a ribbon cutting ceremony to celebrate the re-opening is being planned.
THANK YOU to our community for your patience and for your help designing the new playgrounds. Thanks also to town staff and our Buildings and Grounds Department for their hard work keeping this project moving forward.
About the New Playgrounds
The chosen design and color scheme are the result of a public outreach process. Over 1,500 people participated in the selection and many people also submitted comments, suggestions, and ideas during the public comment period. There was a public presentation of the various playground design options that was held at the MAUHS auditorium on April 13 which was recorded and viewed over 800 times.
The chosen design was fine tuned in response to the comments and suggestions received. The final design incorporates several features that include more musical/auditory components; harness swing systems; different slide options in the ages 5 to 12 large play structure; additional age-appropriate spring rockers in the upper playground; benches for seating; and changing a Volta spinner to an accessible spinner.
View the Public Presentation Video (CLICK HERE)
View the Play By Design Educational Notes PDF (CLICK HERE)
New Playground Design

The playground design “Canopy Discovery” was the overwhelming favorite, with 70% of the total responses. Ramps to fun had 17% and Heights of Adventure had 13% respectively.
About the Design
Design Two – Canopy Discovery (#234-3)

NOTE: The chosen design has been fine tuned in response to comments and suggestions the Town has received. The final design development is incorporating several features and/or elements that include more musical/auditory components, harness swing systems, different slide options in the 5-12 large play structure, additional age appropriate spring rockers in the upper playground, benches for seating, and changing the volta spinner to a non-transfer required accessible spinner.
This playground option tips its hat to the old playground structure with wooden style barriers and features. Both playgrounds include an integrated shade system to help with the heat during the summer months. The pour-in-place rubber surfacing meanders throughout the play space, going under slide exits, swings, and leading people to the accessible play components and transfer stations. The 5-12 area has an active and challenging obstacle course with numerous climbing features. The 2-5 area has developmental focused climbers to improve balance and walking abilities. Each play area also offers age-appropriate swing seats, both include inclusive swing seats and a konnection swing seat (multi-user swing seat). The dish swing provides an excellent opportunity for inclusive play, allowing all children to experience the swinging motion while sharing the dish seat with their friends. The inclusive spinner is centered in the middle of the play space, this merry-go-round allows a wheelchair user to transfer out of their chair and onto the spinner which provides ample back support. Lastly, the shared space has a rocker and a cup style spinner which providing the vestibular motion that all kids love to enjoy. The upper playground is a quaint play space, with swings for both age groups. The playground features 2 slides, 2 climbers, and shade.
ADA/Inclusive Swings:
Rubber Pathways
Freedom Swing Seat (2) (inclusive swing seat with high back support)
Volito Swing Seat (dish swing seat accessible by transfer)
Konnect Swing Seat (multi-generational swing seat – 2 seater)
Freestanding:
Inclusive Spinner (non-transfer)
Sensory Play 5-12 Structure:
CLUBHOUSE FULL BOARD PANEL
CAR ACCESSIBLE REACH PANEL
DRUM ACCESSIBLE REACH PANEL
PISTON PANEL
Sensory Play 2-5 Structures:
(2) MAZE ACCESSIBLE REACH PANEL
BUG PANEL, ACCESSIBLE REACH
3-IN-A-ROW PANEL, 2-5 ABOVE PLATFORM
CHIMES PANEL, 2-5 ABOVE PLATFORM
ABC PANEL 2-SIDED 2-5, ABOVE PLATFORM
POST MOUNTED BELL
Orchid Color Scheme


Timeline for Completion
Now that public input is complete and a final design is chosen, it will be between 2-3 months for the new playground part to be delivered to the site and for construction to be completed. Our hope is to have the new playgrounds open to the public by mid to late summer.
Materials
- PDF of Presentation from Play By Design
- Original RFP for the Playground

Support Paran Recreations and the North Bennington Fire Department by diving into Lake Paran in the middle of winter!
Watch or plunge yourself!
Date and time
Sat, February 4, 2023, 12:00 PM – 2:00 PM EST
Location
Lake Paran Recreations 269 Houghton Street Bennington, VT 05257
Register for the Plunge
https://lakeparanvt.org/events/

(Spring)
Green Up Day, always the first Saturday in May, was launched in 1970 by Governor Deane Davis. In 1979, the non-profit organization Green UpVermont was formed to carry on the tradition of Green Up Day. It is an annual statewide event, when over 22,000 volunteers come together to remove litter from Vermont’s roadsides and public spaces.
The Town of Bennington provides garbage bags and helps coordinate organizations wishing to participate by keeping a list of which roadways and public spaces are being cleaned by whom. For more information or to sign up to clean an area, call the town offices 802-442-1037 or email info@benningtonvt.org

An officially chartered Little League program, we have been offering a positive and exciting youth sports experience for over 50 years. Serving children ages 5 through 12 with a strong emphasis on sportsmanship and teamwork, Bennington Little League continues in a long standing tradition of coaching America’s pastime
Mill Pickleball
A community Pickleball club held in Bennington, VT. The only air-conditioned single court in the area.
160 Benmont Ave, Bennington, VT 05201
(802) 881-9141

White Rocks / Bald Mountain Hike
A local favorite! Park at the trailhead located on North Branch Street in Bennington.
See the description in Trailfinder (CLICK HERE)

Blue Trail
(Hiking, walking, trails)
Part of the Bennington College trail system, through the wooded parts of the campus.
1 College Dr
Bennington, VT 05201
TrailFinder.com

Bennington Rail Trail
Bennington’s newest bike and pedestrian pathway is now available for use. While not fully completed, it is now safe and the public is invited to begin using this new outdoor recreational and non-motorized transportation resource. The Bennington Rail Trail begins at the western end of the Walloomsac Pathway at the public parking area located on Depot Street. The pathway is paved to the intersection with Orchard Road off of Northside Drive. It continues to Emma Street as a packed gravel surface path.
Download Map
The new Bennington Rail Trail provides a bike and pedestrian friendly link between Downtown Bennington and the Northside Drive area which greatly enhances safety for those using the path as well as linking other pathways in town such as the Orchard Village/Willowbrook Pathway and the Kocher Drive Pathway which in turn connects to the East Road Pathway.
Work on the new rail trail has been over 10 years in the works. Removal of vegetation began in the fall of 2021 and throughout the course of 2022, the old rails were removed, new surfaces were added, plus crosswalks, signage, bridge work, and landscaping. Some additional work must be completed by the contractor, but the remaining items do not impact the safety of the new pathway. The cost of the work was 90% paid for through Federal and State grant funding.
An official ribbon cutting ceremony for the new pathway will be held in the Spring of 2023 to celebrate the opening of the new rail trail. This trail is an important part of the overall network of paths throughout the town.
The town has announced the restrictions and trail etiquette for the use of the pathway:
Trail Restrictions
- No motorized vehicles*
- All dogs must be on a leash (please pick up after your dog – it’s the law)
- No alcohol
- No littering
Trail Etiquette
- EVERYONE: KEEP TO THE RIGHT except to pass.
- Ride at a safe speed. (When the path is crowded, you might need to slow down.)
- Warn pedestrians before passing from behind with a bell or by saying “on your left”.
- Pass pedestrians slowly
- Bicycles, use front and rear lights at night.
- Protective head gear is recommended for cyclists, but is not required by VT state law.
*Class 1, 2 and 3 electric bicycles are allowed on the trail. VT statute states that class 1, 2 and 3 electric bicycles are not motor vehicles.
**An individual under 16 years of age shall not operate a class 3 electric bicycle.
Vermont’s e-bike law: https://legislature.vermont.gov/Documents/2022/Docs/ACTS/ACT040/ACT040%20As%20Enacted.pdf

Harmon Hill
(hiking, trails)
Harmon Hill via Long Trail (Appalachian Trail) is a 3.3 mile moderately trafficked out and back trail located near Bennington, Vermont that features beautiful wild flowers and is rated as difficult.
Can be accessed off Route 9 in Woodford near the MacArthur Trail Bridge
https://www.trailfinder.info/trails/trail/appalachian-trail-long-trail-to-harmon-hill
Return to Recreational Opportunities in Bennington and the Region

(Hiking trails, biking, trail maintenance)
The Green Mountain Club Bennington Section is for anyone interested in hiking, walking, biking, snowshoeing, cross-country skiing, trail maintenance, and other outdoor activities.
https://www.benningtongmc.org
Return to Recreational Opportunities in Bennington and the Region
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(Hiking, trails)
The Mile-Around Woods is a 1.3 mile heavily trafficked loop trail located near North Bennington, Vermont that features beautiful wild flowers and is good for all skill levels.
Accessible from McCullough Rd in North Bennington

(Hiking, walking, trails)
The Robert Frost Trail extends two miles from Lake Paran in North Bennington to Route 7A in Shaftsbury. Easy packed dirt trails, pets permitted on leash.
Accessible from either Lake Paran in North Bennington or the trailhead just south of the Robert Frost Stone House on Route 7A in Shaftsbury.
Hunting
(Year-round)
Hunting in Vermont is a tradition that extends back before the country’s founding. In fact, Vermont was the first state with constitutional language that protects its citizens’ right to hunt. With the state’s combination of rolling farmland and thick woods, hunting remains popular and a way to put truly fresh local food on the table.
- https://vtfishandwildlife.com/hunt
- Hunting Preserves near Bennington: https://stepoutside.org/bennington-vt/hunting/
(Year-round)
The mission of the Vermont Fish & Wildlife Department is the conservation of all species of fish, wildlife, and plants and their habitats for the people of Vermont.
Fishing and Hunting License
1 National Life Drive, Davis 2,
Montpelier, VT 05620-3702
802-828-1000

Annual Ice Fishing Derby held at Lake Paran with cash prizes for largest pike and perch.

(swimming, fishing, canoe rentals)
Lake Paran is a small lake with great views of the surrounding mountains, and the only swimming spot on our list that has lifeguards on duty in the summer. The lake and surrounding recreational lands are part of a local nonprofit, Paran Recreations, which is dedicated to helping people enjoy the beauty of nature and having healthy fun outdoors! We are also stewards of the Paran watershed working to keep our environment safe and clean for now and the future.
There is a small, sandy beach to relax on, a floating dock, charcoal grills, a bathhouse and pavilion, and a concession stand with the best grilled cheese sandwiches around. Canoes can be rented for $10 per hour.
269 Houghton Street
North Bennington, VT 05257
- https://lakeparanvt.org/
- (802) 442-8457
- lakeparan@gmail.com

(Spring, summer, fall, swimming)
At 2400 feet, this 398-acre park has the highest elevation campground of any park in Vermont. Woodford is located on a mountain plateau surrounding Adams Reservoir. The high elevation spruce/fir/birch forest provides an ideal setting for the park. Woodford borders the George Aiken Wilderness Area, which is in the Green Mountain National Forest. There are several lakes and ponds in the surrounding area.
142 State Park Road
Bennington, VT 05201
802-447-7169

(swimming, canoe rental, playground, picnic, camp grounds)
Lake Shaftsbury State Park is on an 84-acre parcel surrounding the small but picturesque Lake Shaftsbury. The area operated as a private campground/cabin resort before it became a state park in 1974. It has become a popular park facility in southwestern Vermont.
262 Shaftsbury State Park Rd
Shaftsbury, VT 05262
802-375-9978

(seasonal, swimming)
Another favorite with the locals, the Roaring Branch features a rocky “beach” area, several small pools that are suitable for kids, and one deeper pool that is deep enough for submersing. The river flows right down from the Green Mountains and is incredibly cold, even in the summer. There is ample parking right on Route 9 and enough room to spread out. Weekends can be quite busy here, especially in the late afternoon.
This is a “leave no trace” National Forest Area… please pack out all trash!
Directions: Head east on Route 9 for 2.7 miles or until you pass the Woodford/Bennington town line sign. You will see a parking area on the right. Take a short trail through the woods to the swimming area.

(Trail, hiking, walking, swimming)
The Upper Tubs waterfall is a popular swimming hole for locals that can be reached after an easy hike through the Pownal woodland.
This is a “leave no trace” area… please be sure to pack out all trash.
Walloomsac River
(seasonal, fishing, swimming, tubing)
The Wallomsac River is on the shallow side as it meanders through Bennington, so while the spot under the Burt Henry Covered Bridge may not be deep enough for adults to swim in, it is perfect for kids or for anyone who just needs to cool off. There is a small parking area near the bridge and a park with a few picnic tables, a grassy field, and some plantings. The Henry Bridge is one of three covered bridges spanning the Walloomsac River in Bennington and North Bennington and has very good access to the river below.
River Water Levels
In general, the river is high enough to paddle at 1.65' for kayaks with some scraping over shallow areas. Check the current water level here.
Bennington’s Covered Bridges Water Trail
Does paddling your canoe or kayak past three covered bridges sound fun to you? We often hear that covered bridges and outdoor recreation are two of the main reason that visitors love to come to The Shires of Vermont. And why not throw in some history while you are at it? Or some top-notch trout fishing? You have all of this and more with a paddle along the Walloomsac River in Bennington.
The basic paddling trip will take you about an hour or so, but it can be expanded to almost two hours if you want a longer experience, or shortened for a more beginner friendly trip. Keep in mind that river conditions always affect the amount of time… a faster current will get you there quickly while low water can mean a slow trip and perhaps extra time to carry your boats over the really shallow parts. For the purpose of this article, I’m assuming you already have decent paddling skills on rivers with class I-III whitewater. If this is your first time paddling a canoe or kayak… STOP! Go to a lake or pond for your first experience. I promise you will have a much better and safer experience. You will want to have solid basic paddling skills before paddling a river.
Begin by taking your best route to Silk Road in Bennington, opposite the entrance to Bennington College. Proceed on Silk Road to the Silk Road Covered Bridge. For the shortest and easiest trip, this is where you will put in your boats. Park next to the bridge, carry your boats down the trail right next to the bridge to the Walloomsac River and head downstream. For the full trip, continue through the bridge and proceed about another half mile until you reach the Route 279 Overpass, and park under the overpass on the side of the road. Just past the overpass is a power substation on your right. Opposite the substation is a trail under the overpass to a muddy bank where you can put in your boats and head downstream. If you don’t the look of the muddy put-in at this location, simply drive back to the covered bridge and put in there instead. While muddy to start, this stretch goes by some pretty areas, including a couple of sharp turns in the river to avoid obstacles which is fun for experienced paddlers. Starting from the 279 Overpass it is about 3/4 mile of paddling until you arrive under the Silk Road Covered Bridge.
So why are there covered bridges anyway? One theory is it could be because horses were less likely to “spook” going over a bridge if it was covered. Or perhaps it was less prone to icing over and creating a hazard to travel in winter. The actual primary reason is more in line with simple Vermont practicality… a covered bridge lasted longer than uncovered bridges.
The stretch from the Silk Road Covered Bridge to the Paper Mill Covered Bridge is flat-water and suitable for beginners. It is also dam controlled water, so the water level will never be too low (though it can be too high of course!). This is a lovely stretch with mostly sandy bottoms and a couple of very deep holes where trout like to hide. This is a good area to see ducks, great blue herons, or kingfishers. At about 1.2 miles, you reach a split in the river forming an island where the Paper Mill Covered Bridge is located. You will see a sign at the head of the island warning of the dams just downriver.
At this point, you MUST take your boats out of the water and carry it over the island to avoid the waterfalls on BOTH sides. The official take out is on the river left side of the island (river left is to your left when facing downstream). With it’s steep, undercut bank, I find it very difficult to use that location to take out your boat. Instead, head down the river right side towards the covered bridge and take out on the left just before the covered bridge. Do not go under the bridge where the waterfall is. This is also well marked with a line of warning floats so it’s hard to miss. This take out location is sandy, shallow, and very easy to get out of. This would be your end location if you just wanted a short hour long paddle with no whitewater, so you should park your second vehicle here on the island just over the Paper Mill Covered Bridge. There is interpretive signage here about the bridge and hydro plant, as well as a short trail through the island.
To continue your trip you will carry your boats around the island. From the take out right by the covered bridge, head away from the covered bridge to the other bridge on the other side of the island. Just past that bridge, there is a trail on your right you can follow along back down to the river bank where it ends at a sandy area next to a large pool in the river where you can put your boats back into the river.
From the Paper Mill Covered Bridge to the Henry Covered Bridge is one of my favorite stretches for trout fishing. You will pass numerous deep holes and rocky eddies where trout are waiting. You will also pass Paran Creek where it enters the Walloomsac, and lots of bird watching opportunities. The shoreline is lovely with nice rock features, mossy logs and banks graced with fiddlehead ferns.
This area is also one of the oldest areas of settlement in the region. Originally part of a Dutch settlement called the Walloomsac Patent, it’s fertile river valley made an attractive site for farmers and after the takeover of the Dutch colony by the British and the colony of New York, the stage was set for conflict with the future state of Vermont.
At about 2.3 miles, you will reach the Henry Covered Bridge. This is another good location for a take out if you want to limit your trip to just around an hour, with plenty of parking for your shuttle vehicle. Even if you are continuing on, this is a good place to get out and stretch your legs, and take some photos of this iconic covered bridge. There are picnic tables here, an easy shallow access to the river, and interpretive signage. Did you know that Vermont started at the Henry Bridge? Before Vermont was a state, the land was claimed by both New York and New Hampshire. While New York had the better legal claim, New Hampshire acted first, and began chartering towns in the Hampshire Grants starting with the establishment of Bennington, Vermont’s first town. At this location, an event called “The Breakenridge Standoff” occurred… the first armed confrontation between New York authorities and the local’s who had purchased their land from New Hampshire. This Vermont militia would eventually become the famous Green Mountain Boys, originally led by Ethan Allen, and later by Seth Warner, who’s home was just a short distance away.
Stopping at the Henry Covered Bridge concludes the regular trip, but if you want more, you can continue on for another 2.2 miles to just before the NY/VT border. This final stretch is the most secluded as it meanders through farmland and woods. The fishing continues to be excellent through this stretch, and you may see a deer crossing the river, or even a bald eagle or immature bald eagle. There are also some fairly challenging rapids that approach class III especially in high water. The take out location is at a large pool where the Cold Stream enters the Walloomsac. I recommend taking a walk down to the water to familiarize yourself as to what the take out looks like when you drop off your shuttle vehicle so you don’t accidentally paddle past it. To get to the final take out; go from the Henry Covered Bridge, drive down Harrington Road 1.75 miles to the bridge over Cold Stream. Park on the side of the road just past the bridge. There is an unimproved fisherman style trail from the road down to the river.
Now that you are ready to hit the river, a final word of advice about river etiquette. As a popular trout area, always be respectful of those fishing. When passing fishermen, do so in full stealth mode… with as little disturbance and paddle splashing as possible. If you are approaching a fly fisherman who is standing in the river, attempt to pass behind the fisherman if possible so as to not to disturb the area they are actively fishing. Doing so will minimize your disturbance of the fish you are passing over, and will make everyone happy. Enjoy your paddling experience in Vermont!

(Water playground)
The splash pad will be active during warm months, kid friendly downtown fun. There is also a stage area for performances.
109 North St
Bennington, VT 05201

(Pool, weight room, sauna, showers)
The Bennington Recreation Center is managed in partnership between the Town of Bennington and the Berkshire Family YMCA. They offer indoor swimming and fitness center year round to members and visitors.
Bennington Sports Center
(soccer, basketball, baseball, volleyball)
Bennington Sports and Wellness Center is a focal point for youth of Bennington County and surrounding areas for their recreational activities. This center has created a family fun atmosphere and a great environment for kids and adults to express their talent for many different sports including soccer, basketball, baseball, and volleyball.
230 School St, Bennington, VT 05201
(802)681-7151

Family owned and operated since 1980, offering a 18 lane center with ten pin bowling and High Definition Golf Simulators. Four NEW Golf Courses added! We serve beer & wine and have a full menu available. Perfect for Birthday, Holiday and Corporate Parties with air hockey and pool table available.
219 Northside Drive, Bennington, VT 05201
802-447-7100

Indoor Tennis in Southern Vermont. Professional Lessons, court rentals and pro shop services.
200 Lovers Lane
Bennington Vermont 05201 USA
802-447-7557

Catamount Trail Association
(Skiing, snowshoeing)
Sections 1-7 of the Catamount Trails are a part of Bennington County, backcountry skiing and snowshoe trails that are well maintained.
1 Mill St
Burlington, VT
catamount trail.org

Bromley Mountain
(Skiing, snowboarding, alpine slide, waterslide, aerial adventure park)
Nine lifts carry guests to trails covering 178 of the 300 acres on Bromley Mountain. Lessons and rentals are available.
3984 VT Route 11
Peru, VT
bromley.com

Prospect Mountain
(Nordic skiing, snowshoeing)
Nordic Skiing and Snowshoeing, over 30k of trails, some on National Parks land. Rentals and lessons are available.
204 Prospect Access
Woodford
ProspectMountain.com
Bennington Trail Cruisers
(Summer/Fall, ATVs)
The Bennington Trail Cruisers want YOU!! We are a group of responsible and highly experienced ATV riders that promote safe and legal ATV riding. As a member of the B.T.C. we assure trails are safe, clean, and environmentally friendly.
(518) 892-4719
https://www.benningtontrailcruisers.com/
VAST
(snowmobiles and ATVs)
Founded 50 years ago, Vermont Association of Snow Travelers (VAST) is responsible for the organization of the sport of snowmobiling, maintaining and grooming over 4,700 miles of trails in Vermont. One of the oldest snowmobiling organizations in the U.S., VAST is a non-profit 501-c-3 organization that includes 127 clubs statewide, with over 24,000 members combined. The clubs and their steadfast volunteers, and the landowners that allow riders to cross their land are the backbone of the organization.
https://vtvast.org/

Downtown Walking Tour
(Historical walking tour)
This self -guided walking tour begins at the Downtown Welcome Center on South Street, moves up to Putnam Square and then continues to the Walloomsac River Walk before returning to Putnam Square. Parking is provided at the Welcome Center as well as additional lots designated on the map.
Downtown Bennington, primarily along North and South Streets
Follow the tour.
Return to Recreational Opportunities in Bennington and the Region
Download a copy of the Old Bennington Walking Tour Brochure
Chartered in 1749, Bennington was the first town created in Vermont. In June of 1761 twenty-two settlers from Massachusetts came to Old Bennington, in the wilderness of Vermont, under the leadership of Captain Samuel Robinson to form a Congregational community centered around a village green and a meeting house. The community grew rapidly, hosting many fine homes, schools, a cemetery, post office, and courthouse. It was a self-contained community with many local artisans and merchants to provide services.
The Green Mountain Boys ventured out from here to fight for their land and freedom in the Battle of Bennington. In July of 1777, the Council of Safety met in Bennington and wrestled with the affairs of the newly created Republic of Vermont. At the meeting house they discussed the new Vermont constitution, prohibiting slavery and offering near universal male suffrage. Bennington produced six Vermont governors.
However, as industry grew, activity began to shift downhill along the Walloomsac River, which provided power to operate mills and machinery. Government offices and business soon followed, leaving Old Bennington behind as a quiet
residential community.
Old Bennington reflects a history of change; homes have been taken down, moved, and renovated but the character of individualism and freedom remains and continues in the spirit of Bennington and of Vermont.

(2) Hiram Waters House
(3) Isaiah Hendryx House
(4) Jedidiah Dewey House
(5) Roberts House
(6) Monument to William Lloyd Garrison
(7) Colonel Nathaniel Brush Home
(8) Walloomsac Inn
(9) Old First Church
(10) Bennington Meeting House 1763
(11) The County Courthouse 1847
(12) Site of Ethan Allen’s House 1769
(13) Asa Hyde House
(14) The Catamount Tavern 1767
(15) Old Academy
(16) Samuel Robinson’s log cabin
(17) Samuel Raymond House
(18) General David Robinson House
(19) Richard Carpenter House
(20) The Url Robinson House
(21) Ellenwood-Daniel Conkling House
(22) The Fay-Brown House
(23) Governor John Robinson House
(24) Captain David Robinson House
(25) Bennington Battle Monument
(26) Monument to Seth Warner
(27) Monument to John Stark
(6) William Lloyd Garrison Marker William Lloyd Garrison, the great abolitionist, briefly ran a newspaper, The Journal of the Times, in Bennington from 1828 to 1829 before moving on to establish The Liberator. |
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(7) Colonel Nathaniel Brush Home 1775. Colonel Brush commanded two companies of Vermont militia at the Battle of Bennington. The home was renovated in 1824 and again in the early 1900s. |
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(8) Walloomsac Inn 1771. Originally the Dewey Tavern, it was built by Elijah Dewey, son of Reverend Jedidiah Dewey. During Bennington’s heyday as the jumping-off point for settling the Vermont frontier, the Walloomsac Inn was an important stage stop and one of the village’s commercial and social centers. Prisoners captured at the Battle of Bennington were fed from its kitchens, Presidents Thomas Jefferson and James Madison stayed here in 1791, and President Rutherford B. Hayes held a reception at the Inn celebrating the centennial of the Battle of Bennington in 1877. Mrs. Theodore Roosevelt and her family and later Walt Disney were guests as well. The Inn was in continuous operation as an inn into the 1970s and may be the oldest inn in Vermont. It is currently a private residence. |
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(9) Old First Church 1805 and cemetery. The first Protestant congregation in the New Hampshire Grants was gathered on December 3, 1762 at the Meetinghouse. The First Congregational Church, built in 1805, was dedicated in 1806. Designed by noted architect Lavius Fillmore, with its Palladian window and open belfry, it represents the best of Federal church architecture. It was restored and rededicated as Vermont’s Colonial Shrine in 1937; Robert Frost read a poem at the ceremony. The adjacent cemetery, which predates the church, contains the graves of many of the founders of Bennington, Governors of Vermont, and a mass grave of German and American soldiers killed at the Battle of Bennington. The earliest grave is that of Bridget Harwood who died in 1762. Robert Frost, although not a member of the congregation, is buried here with members of his family. |
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(10) Site of the Bennington Meeting House 1763. On this site stood the original Meetinghouse. The building was 40 x 50 feet and served as a school, a church, and Town Hall. Prisoners from the Battle of Bennington were held here. The Vermont legislature convened here in 1778. it was dismantled after the completion of the new church and parts used in other dwellings in the area. |
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(11) Site of County Courthouse 1847. This was the third Courthouse to be built in Old Bennington. It burned in 1869 and was rebuilt in a location on South Street, moving the base of power from Old Bennington to what is now downtown Bennington. In Vermont a Shire Town is a county seat, and Bennington and Manchester both share that distinction. The June term of the County Court convenes at Bennington and the December term at Manchester. Ethan Allen’s home, built in 1769 was next door. |
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(12) Site of Ethan Allen’s House 1769. Ethan Allen lived here from 1769 to 1775. He is best known as one of the founders of Vermont and for the capture of Fort Ticonderoga early in the Revolutionary War. A historic marker is located a few feet north of the homesite. |
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(13) Asa Hyde House, 1787. Asa Hyde, a skilled cabinet maker, came to Bennington from Norwich, Connecticut, in 1805 to work with the building of the First Church. He is responsible for many of the features of the church, including the columns, pews, and pulpit. |
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(14) Site of The Catamount Tavern 1767. Originally the Stephen Fay Tavern, the building stood on this site and served as the headquarters of Ethan Allen and the Green Mountain Boys, who left from here in 1775 to capture Fort Ticonderoga. General Stark, who commanded the American forces in the Battle of Bennington, conferred here with the leaders of Vermont prior to the Battle. British officers captured in the Battle were housed here for a short time. The bronze statue of the catamount commemorates a stuffed mountain lion that once stood in front of the tavern snarling towards New York, then engaged in land disputes with Vermont. |
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(15) Old Academy 1819. This two story brick building having a step gable front was originally built as a school; later it served as the town library, with the fire department in the basement. Just after it was built a windstorm blew off the belfry, and part of the facade had to be replaced. Note the difference in the brickwork on the front. |
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(16) Site of Samuel Robinson’s Log Cabin 1761. Robinson was the founder of Bennington and leader of the first settlers who bought land titles originating from a grant made by Governor Benning Wentworth of New Hampshire in 1749. |
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(17) Samuel Raymond House 1821. Built of locally made brick, this was the residence of the president of the first bank in Bennington, which was located next door on Bank Street. Extensive renovations around 1930 included a two-story addition and a sunporch. |
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(18) General David Robinson House 1795. General David Robinson was one of the sons of Samuel Robinson. This late Georgian house has elegant columns supporting a frieze above our regional version of the Palladian window. |
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(19) Richard Carpenter House. 1819. One of the many tradesmen in Old Bennington, Carpenter operated a tailor shop with Isaiah Hendryx. The triple window above the door shows renovations carried out in the early 1900’s when it was doubled in size, had its roof line changed and the triple windows added above the door. |
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(20) The Uel Robinson House 1828. Uel was the grandson of Samuel Robinson. The house is a Federal style / Greek Revival clapboard home. Interestingly, two of Uel’s sons moved to South Carolina and served in the Confederate Army during the Civil War. |
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(21) Ellenwood-Daniel Conkling House 1810. This home was enlarged and embellished in the Italianate style in 1859. At one time it sported a cupola. Ellenwood’s carriage shop was next door. |
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(22) The Fay-Brown House 1860. This is the only stone building in the area and was built as a blacksmith shop. It was converted into a dwelling in 1857 and underwent remodeling in 1937. |
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(23) Governor John Robinson House 1781. Robinson, the first Democratic Governor of Vermont, was elected in 1853. The house was built in the vernacular style that combined both Greek Revival and Federal features. |
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(24) Captain David Robinson House 1790. Robinson was a grandson of Samuel Robinson, one of the founders of Bennington. Upon his death he deeded his house to the First Congregational Church for use as a parsonage. |
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(25) The Bennington Battle Monument 1891. Built to commemorate the Battle of Bennington, it is located near the site of the Continental Storehouse which was the object of the British attack. The limestone memorial is 306 feet high, making it the tallest structure in Vermont. President Benjamin Harrison attended its dedication in 1891 on the 100th anniversary of Vermont statehood. Memorials to General Stark, Colonel Warner, and printer Anthony Haswell are located nearby. |
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(26) Monument to Seth Warner. Seth Warner was a resident of Bennington and successor to Ethan Allen as leader of Green Mountain Boys. Later, when the Green Mountain Boys became a Continental Army regiment, he led them to victory at the Battle of Bennington. |
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(27) Monument to John Stark, the hero of Bunker Hill. John Stark, one of the heroes of Bunker Hill, raised 1400 volunteers from New Hampshire and was the overall commander at the Battle of Bennington. Rallying his troops before the battle he said “There they are, boys! We beat them today or Molly Stark sleeps a widow tonight!” The sculpture shows General Stark pointing to the battlefield. |
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