Bennington

Day Trips

Make the most of your day with our curated plans, packed with Bennington's hidden gems and unique experiences!

day 1
Explore Bennington
morning
:

Start your day with a visit to the Bennington Museum to learn about the local history and culture. Don't forget to check out the impressive collection of Grandma Moses paintings.

afternoon
:

After lunch, take a stroll through the picturesque Bennington Battle Monument. The panoramic views from the top are worth the climb!

evening
:

Wrap up your day with dinner at a local restaurant. Enjoy some delicious farm-to-table cuisine while soaking in the charming atmosphere.

day 2
Nature's Beauty
morning
:

Enjoy a hike at the nearby Green Mountain National Forest. The trails offer stunning views and an opportunity to connect with nature.

afternoon
:

Pack a picnic and relax at the scenic Lake Bennington. The area is perfect for fishing, kayaking or simply soaking up the sun.

evening
:

Return to town for a cozy dinner. Try the local pizza joint for a casual yet satisfying meal.

day 3
Arts and Culture
morning
:

Begin your day at the Bennington Museum for rotating exhibitions by local artists. The museum offers insight into the area's creative spirit.

afternoon
:

Take a self-guided art walk around town to admire various local murals and installations. Enjoy your lunch at a quaint cafรฉ along the way.

evening
:

Find a local theatre performance or musical event to attend. Experience the vibrant arts scene that Bennington has to offer.

day 4
Outdoor Adventures
morning
:

Rent a bike and explore the scenic VAST trails. The fresh air and beautiful views will energize your day.

afternoon
:

Stop by a local brewery for a refreshing lunch and sample some craft beers. Relax in the outdoor seating area.

evening
:

Join a guided night tour to learn about the local wildlife. The evening is a great time to be out in nature with a chance to stargaze.

day 5
Fall Foliage Tour
morning
:

Take a scenic drive through the surrounding hills to witness the vibrant fall colors. Stop at overlooks for breathtaking views.

afternoon
:

Visit local apple orchards for cider tasting and pick some fresh fruit. Enjoy the fall flavors at a local eatery.

evening
:

Attend a fall festival or harvest event. Immerse yourself in the seasonal celebrations with live music and local vendors.

day 6
Historic Sites
morning
:

Start the day at Bennington's Old First Church and its beautiful cemetery. The historical significance of the site is deeply rooted in local culture.

afternoon
:

Visit the Bennington Civil War Monument for a glimpse into the town's role in American history. The surrounding park area is perfect for a leisurely lunch.

evening
:

Explore the local dining scene with a focus on historical taverns. Savor traditional dishes that have been passed down through generations.

day 7
Train Ride and Vineyard
morning
:

Take a scenic train ride on the nearby recreation railway. Enjoy the views of the countryside from the comfort of the train.

afternoon
:

Stop at a local vineyard for a wine tasting experience. Learn about the winemaking process while sampling delicious varieties.

evening
:

Dine at the vineyard's restaurant, savoring dishes that pair well with the wines. Experience a romantic atmosphere amidst the vines.

day 8
Stargazing Night
morning
:

Visit the local planetarium for a morning of astronomy. Discover the wonders of the universe through interactive exhibits.

afternoon
:

Take a hike to higher elevations for the best stargazing spots in the evening. Pack a picnic to enjoy the sights during daytime.

evening
:

Bring a telescope to your chosen stargazing location. Spend your evening marveling at constellations and learning about celestial bodies.

day 9
Camping and Bonfire
morning
:

Set out early for a camping adventure in one of Bennington's wooded parks. Gather supplies and ensure you have everything for a great trip.

afternoon
:

Spend the day engaging in outdoor activities like fishing or hiking. Enjoy the serenity of nature and make sure to relax by the water.

evening
:

Gather around a campfire for stories and marshmallow roasting. The perfect ending to a day immersed in the great outdoors.

day 10
Music and Fun
morning
:

Visit a local music venue to explore upcoming acts. Check out any matinee performances that may be scheduled.

afternoon
:

Grab lunch at a diner with live music or open mic events. Experience the local music scene and enjoy some good food.

evening
:

Attend a concert or music festival if one is happening during your visit. Integrate into the local culture and have a great time.

Discover Bennington

Read more in our Bennington 2024 Travel Guide.

Bennington Travel Guide