26 Best & Fun Things to Do in Bennington (VT)

In search of the best and most fun things to do in Bennington, VT?

Bennington is a beautiful city located in Bennington County, Vermont, the United States, just close to Massachusetts and New York.

Recognized as one of the smallest cities in Vermont, Bennington has a population of more than fifteen thousand, according to the 2020 census.

Bennington is a city that every traveler will love to visit, including architecture enthusiasts and history lovers.

There are many attractions in Bennington, some of which include the White Rocks, Kevin’s Sports Pub and Restaurant, Silk Road Covered Bridge, George Aiken Wildflower Trail, Fiddlehead at Four Corners, and many more.

Before you go on your trip to Bennington, let’s explore the top things to do in Bennington, VT.

Things to Do in Bennington, VT

1. Bennington Battle Monument

On your first day in Bennington, visiting Bennington Battle Monument is one of the best things to do.

Bennington Battle Monument was established to remember the Bennington battle, which occurred in 1777.

The battle happened during the period of the American Revolutionary War, so this monument was built as an illustration of how honorable and mighty Bennington fought.

Bennington Battle Monument is characterized by more than 306 feet, making it one of the longest buildings in the state.

Built in 1889, this monument offers fascinating views of three states, including Massachusetts and New York.

You get to learn more about the battles that occurred in the region and enjoy the beautiful views of several miles from the top of the deck.

Bennington Battle Monument is open daily from 10am-5pm from May to October but closed during the cooler months.

Address: 15 Monument Cir, Bennington, VT 05201, United States

2. Downtown Bennington Historic District

Certainly, your trip to Bennington wouldn’t be complete without visiting the Downtown Bennington Historic District.

Downtown Bennington Historic District is a location that shows the level of bustling and hustling intensity in the city.

You’ll find several beautiful structures built in various unique architectural styles like Greek revival, Italianate, and neoclassical architecture.

Downtown Bennington Historic District features structures built in the 19th and 20th centuries, filled with several art galleries.

You’ll also find many restaurants offering different dining options, live theatres, parks, and other exciting options in the area.

Address: Bennington, VT 05201, United States

3. The Old First Congregational Church

The Old First Congregational Church is a historical church established in 1805, making it the oldest church in the state.

It is widely recognized as the first protestant Church in Vermont, which began in 1762, way before the church was built.

The early residents held meetings in what was called the meeting house and later relocated to the main building when the church was built.

The Old First Congregational Church is open to everyone all the days of the week throughout the year, although Time for its opening might vary.

This church takes you on an excursion through the path of history, and it was also named Vermont Colonial Shrine by the Vermont Legislature.

Address: 1 Monument Circle, Bennington, Vermont 05201 United States

4. The White Rocks

For outdoor enthusiasts, add a visit to the White Rocks to your list of fun things to do in Bennington, VT for an amazing adventure.

The White Rocks feature a long trail of approximately 6.4-km (4-mile) and is a popular destination for hikers.

This trail offers picturesque views of the mountain surrounding it and spectacular views of the city. The White Rocks are the shoulder of Bald Mountain with exactly 2, 400-feet.

The White Rocks is quite easy to navigate and leads you to the Wilderness of Glastonbury, consisting of a lovely small stream.

Walk until you reach the apex of the white Rocks, which is an excellent place to meditate and enjoy the quietness and peace away from the noise in the world.

Address: 449 NorthBranch St, Bennington, VT 05201, United States

5. Bennington Lanes

Bennington Lanes is a family fun center in Bennington, established in 1980, which has become a part of many childhood memories.

This center is a favorite spot for many families to hang out and spend quality time in the city, where they can create new beautiful memories.

Bennington Lanes consists of eighteen different lanes; no need to bother about the place being crowded or not but everyone will have a good time.

The fun center features a full-service bar that offers a wide variety of delightful drinks served chilled with a small food menu to match up.

Bennington Lanes is open on Saturday from 12pm-10pm, Sunday from 12pm-5pm, Monday & Tuesday from 2pm-9pm, Wednesday from 10am-2pm, and Friday from 2pm-10pm.

Address: 219 Northside Dr, Bennington, VT 05201, United States

6. Bennington Cinemas

If you’re a bit confused about where to watch your favorite blockbuster movie, obtaining your movie tickets at Bennington Cinemas is one of the best things to do in Bennington, VT.

Bennington Cinemas is an awesome theater where you can just relax and be sure to have a terrific movie experience.

The theater shows newly released movies that are trendy and perfect for the whole family, including recent animated movies for both kids and adults.

Bennington Cinemas is always clean and well maintained, with comfortable seats, large flatscreen TVs, and fantastic sound system.

The theatre is designed in a way that from every point where you’re seated you would be able to see the stage without stress and any obstruction.

The staff is professional and polite when dealing with visitors, plus the concession that offers freshly made popcorn and chilled drinks.

Address: 125 Phyllis Ln, Bennington, VT 05201, United States

7. Bennington Museum

Are you interested in discovering new facts? Visiting Bennington Museum is one of the best things to do in Bennington, VT.

Bennington Museum was established in 1852 and is recognized for housing a comprehensive and outstanding collection of local and regional art history.

The museum is home to the largest collection of the original paintings made by Grandma Moses and other diverse exhibitions.

Bennington Museum showcases several paintings, artifacts, and stonewares. The Museum was established to promote and showcase the level of creativity in the city of Bennington and other areas during the 18th century.

The Museum hosts some exciting events and is open for free throughout the year for visitors from the age of seventeen upwards.

Address: 75 Main St, Bennington, VT 05201, United States

8. Kimberly Farms

Are you in for a more unique experience? Visiting Kimberly Farms is one of the best things to do in Bennington, VT with your friends and family.

Kimberly Farms has been in existence for nearly thirty years now, spanning across sixty acres featuring several essential amenities.

The farm features many horse riding tracks ideal for the entire family or a group of friends who want to explore the various horses.

Kimberly Farms assures visitors a safe ride as a professional guide is always around to offer assistance and guidance.

While riding, you also get to enjoy the amazing views provided by the mountains and the panoramic views of the state surrounding the Kimberly Farms.

Kimberly Farms offers horseback riding lessons, exciting events, and day camps. This is a place you should definitely, that will bring your cowboy dreams to life.

Address: 1214 Cross Hill Rd, North Bennington, VT 05257, United States

9. Oldcastle Theatre Company

Oldcastle Theatre Company officially opened in 1972 as a performing arts theatre in Bennington, offering great entertainment for little cost.

The theatre is a venue for numerous events performed by talented local artists, many of the plays produced here have been shown all over the country and worldwide.

Oldcastle Theatre Company has been in existence for more than fifty years; during this period, it produced more than three hundred dramas.

The company has played a major role in the world of art and entertainment, also providing a means for local artists to be heard and seen.

Oldcastle Theatre Company produces incredible plays through the hard work of professional designers, actors, writers, and directors in the company.

Address: 331 Main St, Bennington, VT 05201, United States

10. Bennington Recreation Center

To your list of fun things to do in Bennington, VT, add a day at Bennington Recreation Center, a perfect place to spend the day.

Bennington Recreation Center features a public swimming pool open to everyone and a favorite place for swimmers.

The center offers you a chance to cool off during the hot summer days as you get to relax in the large indoor swimming pool.

Bennington Recreation Center’s swimming is easily accessible by everyone including the handicapped, and also features stairs and lifts.

The recreational center also features a gym for those who want to work out to keep fit or shade some extra calories.

Bennington Recreation Center is always open on Saturday from 9am-6pm, Monday, Wednesday & Friday from 6am-8:30pm, and Thursday from 8am-8:45pm.

Address: 655 Gage St, Bennington, VT 05201, United States

11. Publyk House

For an exceptional dining experience, add a visit to Publyk House to your list of top things to do in Bennington; you will be grateful you did.

Publyk House was built more than forty years ago in an old-fashioned European public housing style which has grown immensely into a community center.

The restaurant serves as a meeting place for locals and visitors, where they get to enjoy savory food and delicious drinks.

Publyk House offers a lively, calm, and friendly atmosphere with a beautiful interior and a crystal clean and well organized environment.

Some of the meals served include spinach salad, creamy shrimp scampi, warm Buffalo chicken dip, blackened salmon fillet, Publyk House meatloaf, roast turkey dinner, black bean burger, lobster mac & cheese, and more.

The restaurant offers a wide variety of drinks, including best quality spirits, beers, juices, and many others. Publyk House is well ventilated to keep the atmosphere cool during the summer months, and during the winter season, patrons are kept warm.

Address: 782 Harwood Hill Rd, Bennington, VT 05201 United States

12. Kevin’s Sports Pub and Restaurant

Are you still searching for a restaurant to dine? Kevin’s Sports Pub and Restaurant is the perfect choice for you.

Kevin’s Sports Pub and Restaurant take you back in time with a beautiful old-fashioned, well-designed interior that gives you the true old-school vibes.

The restaurant provides a comfortable dining area and a nice outdoor patio; you can choose to enjoy your food anywhere you want.

Kevin’s Sports Pub and Restaurant offer a unique food menu peculiar for each day, Thursday for Italian dishes, Wednesday is Mexican cuisine, and Tuesday is the Steak night.

There is a full-service bar that offers a wide variety of drinks with fantastic taste and quality you haven’t had before.

Kevin’s Sports Pub and Restaurant is open on Saturday & Sunday from 11am-12am, and Monday to Friday from 11am-9m; get ready for the energetic live entertainment.

Address: 27 Main St, North Bennington, VT 05257, United States

13. Silk Road Covered Bridge

Looking for a perfect escapade from all the noise, add a stop to Silk Road Covered Bridge to your list of fun things to do in Bennington, VT.

Silk Road Covered Bridge was constructed in 1840 by Benjamin Sears, a spectacular builder from a family of builders.

The bridge was built as a one Lane Road, which serves as the link between North Bennington and downtown Bennington.

Silk Road Covered Bridge is one of the three bridges in this region; in 2011, it faced an attack by a mighty flood which led to a great damage.

The bridge was restored and later reopened; when you visit Silk Road Covered Bridge, make sure you take beautiful pictures and fully explore it

Address: Silk Rd, Bennington, VT 05201, United States

14. Laumeister Art Center in Southern Vermont College

Laumeister Art Center in Southern Vermont College is an art gallery that offers you an amazing experience in Bennington.

The art gallery is dedicated to bringing the people closer to the beautiful art world and encouraging their full participation in fine and cultural arts.

Laumeister Art Center in Southern Vermont College showcases an incredibly large Native American art collection.

This art gallery hosts different kinds of events and exhibitions offers the best cultural sets, fine arts, performing arts, and graphics arts.

Laumeister Art Center in Southern Vermont College consists of seven different galleries, a covered bridge museum, a theater with a seating capacity of three hundred & fifteen, and art studios.

The art gallery is solely focused on supporting the community art section; Laumeister Art Center in Southern Vermont College is open on Saturday and Sunday from 10am-5pm

Address: 44 Gypsy Ln, Bennington, VT 05201, United States

15. Walloomsac Farmers’ Market

For your next family meal, add shopping at Walloomsac Farmers’ Market to your list of things to do in Bennington, VT.

Walloomsac Farmers’ Market is a popular farmers’ market in the city, which draws many locals and visitors from different parts of the state.

You can shop for a wide variety of seasonal produce, fresh farm products, and baked goods for reasonable costs.

Walloomsac Farmers’ Market is all about encouraging patrons to cook and eat healthy by offering the best products.

The market also features an amazing live entertainment that keeps the energy and vibrancy of the people alive.

Shopping at Walloomsac Farmers’ Market is a sure way to support local businessmen and women in the town. Walloomsac Farmers’ Market is open on Saturday from 10am-1pm, and Tuesday from 3:30pm-5:30pm.

Address: Walloomsac Pathway, Bennington, VT 05201, United States

16. Benner’s Pizza

Are you hungry? Add a visit to Benner’s Pizza to your checklist of things to do in Bennington, VT; it is housed in an ancient white colonial style building.

 Benner’s Pizza’s building was constructed in 1816

and has undergone renovation to help preserve the structure and its history.

This restaurant is family owned and operated, which serves the best and most deliciously prepared pizza, which comes with different toppings.

Benner’s Pizza serves a wide variety of salads, soups, pizza, sandwiches, burgers, chicken wings, calzones, and more.

Every meal is freshly made using fresh and locally sourced ingredients, giving it a unique taste and overwhelming freshness.

 Address: 604 Main St, Bennington, VT 05201 united states

17. Fiddlehead at Four Corners

Are you obsessed with artwork? Add a visit to Fiddlehead at Four Corners to your list of fun things to do in Bennington, VT.

Fiddlehead at Four Corners is a lovely art gallery located in the center of the city, showcasing an enormous collection of artworks.

The gallery features beautiful craftworks such as pottery, oil paintings, blown glass, metal or wooden artworks, photographs, and more.

Fiddlehead at Four Corners also features outstanding film photography; the gallery is a piece of art located in a refurbished old marble bank.

This art gallery is open all days of the week from 9am-6pm to everyone, both visitors and residents, free of charge.

Address: 338 Main St, Bennington, VT 05201, United States

18. Park-McCullough House

Due to how incredible Park-McCullough House actually is, it should be added to your list of fun things to do in Bennington, VT.

Park-McCullough House occupies exactly nine acres and stands as one of the remaining Victorian mansions which have been properly preserved.

The mansion has thirty-five rooms, and it is open for tours; you can also request a guided tour, so get ready to have a good time.

Park-McCullough House was erected in 1864 and was designed by Henry Dudley, inspired by the prominent Revival and Second Empire styles.

The house sits on two hundred acres of land, a venue for private events, including birthday parties, wedding parties, retirement parties, and more.

Park-McCullough House is open to visitors who want to tour the house and the entire property; make sure you check the website before visiting.

Park-McCullough House is open on Sunday from 12pm-4pm, Saturday from 10am-4pm, and Friday from 10am-2pm (closed from Monday to Thursday).

Address: 1 Park St, North Bennington, VT 05257, United States

19. The George Aiken Wildflower Trail

The George Aiken Wildflower Trail spreads over six acres of land, and it is located in the Bennington Museum.

This is a large garden with a fantastic trail excellent for jogging, hiking, running, and walking, mostly surrounded by nature.

The George Aiken Wildflower Trail truly stands out due to its breathtaking views from the beautiful wildflowers.

This trail also serves as an educational center where visitors learn about various wildflowers species because every plant is marked as a way of identification.

You can take a quiet walk down the trail while also enjoying the beauty and tranquility of the environment, making it a perfect place to reflect.

Address: 77 Main St, Bennington, VT 05201, United States

20. Green Mountain Oasis Day Spa

Irrespective of how much you want to explore the city, take a break and visit a fantastic spa that offers highly beneficial services.

Green Mountain Oasis Day Spa is the best place for you in Bennington; they will help you rejuvenate and get relief from your stress.

The homey and welcoming ambiance of the spa gives visitors that calm, restful, and soothing environment that will make them want to stay for long.

Green Mountain Oasis Day Spa offers raindrop therapy massages, pain therapy massages, Oasis signature massage, sports massages, and more.

Every kind of massage has its purpose, either to heal injuries acquired during sports, to stop anxiety, for chronic pains, pregnancy, to relieve stress, and more.

Green Mountain Oasis Day Spa also offers facials, body wraps, treatments, and spa pedicures.

The staff is well trained and certified to offer this kind of services, they know what is fit for every person and how to attend to their guest.

Address: 469 Main St, Bennington, VT 05201, United States

21. The Mile-Around Woods

When you’re in the mood to go outdoor, visiting the Mile-Around Woods is one of the fun things to do in Bennington, VT.

The Mile-Around Woods is a favorite hiking destination in the city established to serve as a refuge for local flora and fauna.

This preserve is an excellent place for hiking, bird watching, and walking as you also enjoy the beautiful environment and peaceful ambiance.

The Mile-Around Woods is a pet-friendly location, so you may choose to come with your furry friend and also go on a walk together.

When you visit this place, you will surely appreciate the work of nature and how beautiful this place is; you can visit during the summer or winter.

Address: Woods Ln, North Bennington, VT 05257, United States

22. Jensen’s Family Restaurant

Jensen’s Family Restaurant officially opened its doors in 1961 and has been serving the public with the most delicious meals they could get.

Even after being in existence for years, the cost of the meals changed, but the uniqueness and tastes of the meals didn’t.

Jensen’s Family Restaurant features a cozy outdoor patio ideal during the hot days for better relaxation, while the greenhouse seating is perfect during the freezing days.

The popular meals at the restaurant include French fries, hot dogs, chili dogs, hamburgers, chicken French onion soup, clams strips, and more.

They also offer an extensive drink menu, including root beer, lemonade, raspberry iced tea, mt. Dew, sugar free root beer, kids’ soda, and different flavors of juices.

Jensen’s Family Restaurant is open on Tuesday from 8am-2pm, Wednesday to Friday from 8am-8pm, Saturday from 8an-8pm, and Sunday 8am-4pm.

Address: 332 North St, Bennington, VT 05201 United States

23. The Mt. Anthony Country Club

The Mt. Anthony Country Club has one of the best golf courses in Bennington and a popular place for golf fans, whether you’re a beginner or an expert.

Imagine swinging your club in an incredibly beautiful natural golf course that offers you the challenges and excitement you need.

Mt. Anthony Country Club is a top-notch 18-hole championship golf course constructed in 1897, a place that will make you appreciate the beauty of greens.

This is also a great place for various kinds of private events, including wedding celebrations and more. Mt. Anthony Country Club features a gift shop that offers a wide variety of golf equipment and a nice cafe where you can enjoy different delicacies and drinks.

Address: 180 Country Club Drive, Bennington, VT 05201 United States

24. Madison Brewing Company, Pub & Restaurant

Madison Brewing Company Pub & Restaurant is a popular attraction in Bennington, known for its unique craft beer and delicious meals.

This brewhouse shares a strong relationship with the community and has been operating in Bennington since 1996. The brewhouse has been consistent in its mission to offer people top-quality beers and mouth-watering watering foods in a lovely environment.

They have a broad selection of beer styles, from traditional Old-world styles to New England Style IPAs, and a full-service bar.

This attraction is a great place to relax and enjoy beers with friends and loved ones.

Address: 428 Main St, Bennington, VT 05201, USA

25. Lake Paran Recreations

Lake Paran Recreations is in North Bennington, VT, a voluntary organization generously run by indigenous nature enthusiasts.

A group of locals from North Bennington established Pancan Recreations in 1960 and bought a six-acre property beside the shores of Paran for recreation and swimming activities.

Its goal is to assist the residents and visitors in exploring and enjoying nature’s beauty in Southern Vermont and create healthy and accessible outdoor recreation.

During summer, this place is a favorite hangout spot for residents to enjoy the views of the beautiful lake and the watershed surrounding the area.

Lake Paran Recreations features a mini beach area, lawns, sand volleyball court, concession stands, charcoal grill, kayak and canoe rentals, floating rafts, and lifeguards. Their summer events include the 3rd of July Fireworks, Stone Kipping Festival, and “Our Village ” Summer Camps.

Apart from summer, other seasonal activities include fishing and ice fishing, ice skating, outdoor Education, and Youth and Adult Programs. You can also utilize its Paran Plunge, rental services, and Paran-Frost Trail access.

Address: 269 Houghton St, North Bennington, VT, USA

26. Norman and Selma Greenberg Conservation Reserve

The Norman and Selma Greenberg Conservation Reserve is a 96-acre property in Bennington, VT. This land was purchased and transformed into a nature preserve through a grant and financial funding from a Vermont Housing Estate and conservation board.

The 96-acre nature preserve comprises an open meadow, a forested hillside at Bennington’s South entrance, and a wetland.

This one-time dairy farm is currently a classroom for kids and college children. The trail in the Preserve cuts across an open meadow and a wetland to connect other tracks at a distance.

The woodland trails travel across different forest stands to showcase artifacts of the era when the hillside witnessed many farming activities. The trailhead offers parking spaces for vehicles.

Address: 414 Route 7S, Bennington, VT 05201, USA

Check out more cities in Vermont, here is  a guide on things to do in San Montpelier, and fun things to do Brattleboro in for a fun time

Plan a Trip to Bennington

Bennington is a city rich in history and culture, there are lots of cultural establishments and traditional festivals to visit or attend.

In a city like Bennington, you might get confused about what to do or where to visit due to the variety of fun attractions and activities.

The city is suitable for everyone, having something in store for individuals of all ages including kids. Do plan a visit to Bennington!