Bennington

Day Trips

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

day 1
Arrival and Exploration
morning
:

Arrive in Bennington and check into your cozy accommodation. Take a leisurely stroll around the picturesque downtown area, soaking in the charming architecture and small-town vibe. Stop by a local café for a hearty breakfast to fuel your day ahead.

afternoon
:

Visit the Bennington Museum to learn about the town’s rich history and its connection to American art. Explore the nearby Bennington Battle Monument, where you can climb to the top for panoramic views of the surrounding Green Mountains. Enjoy a light lunch at a local eatery, sampling some quintessential Vermont cuisine.

evening
:

Dinner at a farm-to-table restaurant will provide an authentic taste of Vermont's local produce. Afterward, you might catch a live music performance or a community event at a local venue. Wind down your evening with a peaceful walk through the town to enjoy the stars twinkling above.

day 2
Art and Nature
morning
:

Start your day with a hike in the nearby Green Mountain National Forest to immerse yourself in the stunning natural surroundings. The scenic trails will offer breathtaking views and a chance to connect with nature. Pack a picnic breakfast to enjoy amidst the beauty of the great outdoors.

afternoon
:

After your hike, visit the Robert Frost Stone House Museum, where the famous poet resided. Enjoy a guided tour and learn about special features of his life and work. Head back to town for a leisurely lunch, then explore the local art galleries showcasing works by regional artists.

evening
:

Dine at a historical inn known for its rustic charm and delicious menu. Participate in a storytelling evening, where locals share tales of Bennington's past. Cap the night with dessert at a nearby ice cream shop, a perfect way to end a delightful day.

day 3
Cultural Immersion
morning
:

Begin your day with a visit to the nearby Shires of Vermont Scenic Byway, a beautiful drive that reveals the unique character of the region. Stop at roadside farms to taste fresh produce and homemade goods. Afterward, enjoy breakfast at a local diner where residents enjoy their morning coffee.

afternoon
:

Engage in a workshop at the Bennington Center for the Arts, allowing you to unleash your creativity through various mediums. Spend some time exploring the local artisan shops and galleries before having lunch at a café that emphasizes local ingredients. The afternoon culminates in a visit to the Bennington Potters for a pottery demonstration.

evening
:

Savor a delightful dinner at a fine restaurant known for using seasonal farm produce in its dishes. Attend a seasonal festival or arts event that showcases local talents and community spirit. After enjoying the festivities, head back to your accommodation for a well-deserved rest.

day 4
History and Heritage
morning
:

Visit the Old First Congregational Church, a stunning architectural gem that stands as a reminder of Bennington’s long history. Follow this with a visit to the Bennington Cemetery, where notable figures are buried, including Robert Frost. Enjoy breakfast at a café with outdoor seating to enjoy the morning air.

afternoon
:

Delve deeper into the Revolutionary War history by exploring the historical markers and sites around town. Have lunch at a historic tavern that offers a taste of traditional New England fare. Spend the afternoon exploring the scenic riverside parks nearby for a relaxing stroll.

evening
:

Experience dinner at a historic restaurant, where the walls are lined with memorabilia reflecting Bennington’s past. Attend a lecture or guided ghost tour for an engaging evening of local legends. Wrap up the day with a nightcap at a local pub, enjoying the warm atmosphere.

day 5
Outdoor Adventure
morning
:

Take a guided rafting trip on the Battenkill River, experiencing the thrill of nature’s waves. Enjoy breakfast on the riverbank, surrounded by lush greenery, and gear up for an adventurous day ahead. The morning air will fill with the sound of laughter and nature as you begin your journey.

afternoon
:

Continue your outdoor escapades by hiking the Long Trail, a beautiful stretch offering stunning vistas of the valley. Pack a picnic lunch to enjoy on the trail while taking a moment to appreciate the natural beauty surrounding you. The afternoon is full of exploration and encounters with wildlife.

evening
:

After an exhilarating day, find a rustic lodge for dinner, where hearty meals will revive you after the adventures. Share stories with your companions about the day’s experiences under a starry sky. As the evening winds down, settle around a bonfire to reflect on your outdoor journey.

day 6
Local Flavors and Craft Beverages
morning
:

Start your day at a local farmer’s market, where the fresh produce and homemade goods bring the flavors of Bennington to life. Sample local delights while enjoying breakfast from food vendors. The vibrant atmosphere will energize your morning as you mingle with community members.

afternoon
:

Visit local breweries and distilleries for guided tastings, learning the craft behind Vermont's renowned beverages. Enjoy lunch at a brewpub offering a menu prepared with locally sourced ingredients. Take a leisurely stroll afterward to savor the beautiful landscapes of the surrounding area.

evening
:

Dine at an upscale restaurant that showcases local craft beers and wines alongside elevated dishes. Engage in a local food tour that leads you through the best eateries in town for a memorable collective dining experience. Conclude your evening back at the brewery for some live music and a lively atmosphere.

day 7
Scenic Views and Relaxation
morning
:

Start your day with a visit to the Bennington Viewpoint, located on a scenic overlook with spectacular views of the mountains and valleys. Enjoy breakfast outdoors, appreciating the serene setting. Capture the early morning light with a few photographs to remember the beautiful scenery.

afternoon
:

Spend the afternoon at the Lake Paran Recreation Area, where you can enjoy swimming, kayaking, or picnicking by the lake. Have lunch at a grill that overlooks the water, providing a perfect spot to relax. Explore the trails that surround the lake, perfect for an afternoon nature walk.

evening
:

As the day winds down, enjoy dinner at a lakeside restaurant while watching the sunset reflect on the water. Afterward, participate in open mic night at a local venue, showcasing talent from the community. Reflect on your day’s activities around a cozy fire pit at your accommodation.

day 8
Departure and Reflection
morning
:

Enjoy a leisurely breakfast at your favorite café in Bennington, taking time to savor the flavors one last time. Reflect on your adventures over the past days, reminiscing about the places visited and memories made. Take a final stroll through downtown, picking up any last-minute souvenirs.

afternoon
:

Before leaving, visit a local spa for a relaxing treatment to unwind before your journey home. Enjoy a light lunch at a nearby spot that serves quick bites and local drinks. As your time in Bennington comes to an end, enjoy the tranquil ambiance around you.

evening
:

Depart from Bennington with a heart full of memories and a camera full of photos. Whether it's with friends or family, share stories of your adventures on the ride home. Arrive back refreshed and inspired by the beautiful experiences you've had in this charming town.

Discover Bennington

Read more in our Bennington 2025 Travel Guide.

Bennington Travel Guide