5-Day Ultimate Itinerary in Bennington, Vermont

Day 1: Explore Historic Bennington

Bennington, Vermont

8:00AM

Breakfast at The Coffee Bar

Start your day with a delicious breakfast at The Coffee Bar, known for its artisan coffee and fresh pastries, setting the perfect tone for your Bennington adventure.
Located in downtown Bennington.
USD12, 1 hour

9:30AM

Visit Bennington Battle Monument

Climb to the top of the tallest stone monument in the U.S. for panoramic views of Vermont and to learn about the pivotal battle of the American Revolution.
A short 5-minute drive from the coffee shop.
USD4, 2 hours

12:00PM

Lunch at The Publyk House

Enjoy traditional New England fare with plenty of local flavors featuring farm-to-table dishes.
A 3-minute drive from the monument.
USD20, 1.5 hours

1:30PM

Explore Bennington Museum

Delve into history and art, showcasing works from local artists and artifacts that celebrate the town’s rich heritage.
A 5-minute drive from lunch.
USD10, 2 hours

4:00PM

Stroll through the Bennington Cemetery

Visit the final resting place of famous figures like Robert Frost while soaking in the area’s natural beauty.
A 5-minute walk from the museum.
USD0, 1 hour

6:00PM

Dinner at The Olde Banner

Enjoy dinner at The Olde Banner, famous for its hearty meals and welcoming atmosphere.
A 2-minute drive from the cemetery.
USD25, 1.5 hours
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Day 2: Nature and Art

Bennington, Vermont

8:00AM

Breakfast at The Bagel Shop

Grab a fresh bagel and coffee from The Bagel Shop before heading into the great outdoors.
Located downtown.
USD8, 1 hour

9:30AM

Hike at the Long Trail

Experience Vermont’s natural beauty with a hike along the Long Trail, offering both easy and challenging routes.
About a 15-minute drive to the trailhead.
USD0, 3 hours

1:00PM

Lunch at The Creamery

Refuel with a delicious sandwich at The Creamery, renowned for its sweet treats and casual vibe.
15-minute drive back to Bennington.
USD15, 1 hour

2:00PM

Visit Southern Vermont Arts Center

Explore local art exhibitions and beautiful grounds that often host outdoor art installations.
A quick 5-minute drive from lunch.
USD10, 2 hours

4:30PM

Scenic Cartwright Park

Relax and take in the views at Cartwright Park, perfect for a serene walk or picnic.
A 10-minute drive from the arts center.
USD0, 1 hour

6:00PM

Dinner at Bennington Pizza Plaza

Indulge in a delicious pizza with locally sourced toppings at this popular local pizzeria.
15-minute drive from the park.
USD18, 1.5 hours
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Day 3: Cultural Discoveries

Bennington, Vermont

8:00AM

Breakfast at The Blue Benn Diner

Enjoy a classic diner breakfast with options ranging from pancakes to hearty skillet meals.
Short drive to the diner.
USD12, 1 hour

9:30AM

Tour The Bennington Potters

Take a guided tour of the pottery studio and browse their beautiful handmade ceramics.
A 10-minute drive from the diner.
USD7, 1.5 hours

11:00AM

Visit the Bennington Historical Society and Museum

Learn about the area’s fascinating history from Revolutionary War times to today.
A short 5-minute drive.
USD5, 1 hour

12:30PM

Lunch at The Stagecoach Tavern

Savor some hearty New England comfort food in a cozy setting.
A 5-minute drive from the museum.
USD20, 1.5 hours

2:00PM

Explore the Bennington Museum's Art Gallery

Take a deeper look into the local art scene and view works from renowned artists.
5-minute drive back to the museum.
USD10, 2 hours

4:30PM

Relax at Lake Paran

Wind down by the lake, perfect for a peaceful stroll or quiet moments enjoying nature.
15-minute drive from museum.
USD0, 1.5 hours

6:00PM

Dinner at The Publyk House

Revisit this local favorite and try different dishes for a delightful dinner experience.
15-minute drive back into town.
USD25, 1.5 hours
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Day 4: Outdoor Adventures

Bennington, Vermont

8:00AM

Breakfast at The Coffee Bar

Fuel up once again with coffee and delightful breakfast options from this local gem.
Located downtown.
USD12, 1 hour

9:30AM

Visit Hogback Mountain Scenic Overlook

Spend the morning at a stunning viewpoint that overlooks the Green Mountains, ideal for photography.
About a 25-minute drive.
USD0, 1 hour

11:00AM

Go for a Bike Ride on the Bennington Rail Trail

Rent a bike and enjoy a leisurely ride along this picturesque trail.
Trail starting point is close by Hogback Mountain.
USD20, 2 hours

1:00PM

Lunch at Papa Frank's Italian Restaurant

Delight in hearty Italian dishes in a family-friendly atmosphere.
A 20-minute drive back to town.
USD18, 1.5 hours

2:30PM

Take a Guided Historic Farm Tour

Visit a local farm and learn about sustainable practices while enjoying scenic views.
10-minute drive from lunch.
USD15, 2 hours

5:00PM

Explore Bennington's Craft Breweries

Sample local craft beers and learn about Vermont's brewing traditions at a couple of breweries in downtown.
5-minute drive from the farm.
USD0 (tasting fees may vary based on selected samples), 1.5 hours

7:00PM

Dinner at The Olde Banner

Refuel after the day’s adventures with a hearty meal at this beloved local spot.
5-minute drive from the breweries.
USD25, 1.5 hours
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Day 5: Relaxation and Reflection

Bennington, Vermont

8:00AM

Breakfast at The Blue Benn Diner

Finish your trip with a nostalgic breakfast at this iconic diner with a great retro vibe.
Short drive to the diner.
USD12, 1 hour

9:30AM

Visit the Bennington Museum once more

Reflect on the cultural insights gained during your trip as you revisit the museum.
5-minute drive from the diner.
USD10, 2 hours

11:30AM

Relax at the Bennington River Walk

Take a peaceful stroll along the river and enjoy the sounds of nature one last time.
A 5-minute drive from the museum.
USD0, 1 hour

1:00PM

Lunch at The Creamery

Enjoy one last meal at The Creamery, savoring their classic sandwiches and ice cream.
15-minute drive back to crowded areas.
USD15, 1.5 hours

2:30PM

Visit the Bennington Potters for last-minute shopping

Grab unique gifts and souvenirs crafted by local artisans.
10-minute drive from lunch.
USD0 (cost depends on purchases), 1 hour

4:00PM

Departure from Bennington

Say goodbye to this charming town and take with you lasting memories of your Vermont adventure.
Depending on travel plans.
USD0, N/A
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