Bennington Battle Monument
Day 1: Arrival and Exploration in Bennington
Morning:
Arrive in Bennington, VT.
Start your day with breakfast at the Blue Benn Diner, a quaint, authentic diner in Bennington with a retro vibe, serving traditional American breakfast and lunch options. Famous for its old-school jukeboxes at each table.
Afternoon:
Visit the Bennington Museum, home to a diverse collection including Grandma Moses paintings and Revolutionary War artifacts.
Stop by Bennington's historic church, The Old First Church, known for its beautiful colonial architecture and as the burial site of the famed poet Robert Frost, whose gravestone famously reads, "I had a lover's quarrel with the world."
Explore the Bennington Battle Monument, the tallest structure in Vermont, offering panoramic views from the top. This monument commemorates the Battle of Bennington, a turning point in the Revolutionary War.
Evening:
Have dinner at The Publyk House, located on a hill overlooking Bennington, this restaurant offers a cozy, rustic setting with a fireplace and serves traditional American dishes made from local ingredients.
Check into your accommodation.
Day 2: Adventure in THE NORTHSHIRE
Hildene, The Lincoln Family Home
Morning:
Drive to Manchester (approx. 30 minutes from Bennington).
Grab a delicious brunch at The Copper Grouse, a tavern in Manchester serving classic New England comfort food in a warm, inviting atmosphere, ideal for relaxing after a day of activities.
Ready to game? Old school rules? Take the kiddos over to Pastime Pinball, an all-inclusive pinball museum and arcade that brings a dash of nostalgic entertainment to the modern day. The venue features a vibrant collection of over 60 pinball machines ranging from classic to contemporary models, all set to free play for unlimited enjoyment.
Afternoon:
Visit Hildene, The Lincoln Family Home, to explore the estate and beautiful gardens. The summer home of Robert Todd Lincoln, the son of President Abraham Lincoln, the estate features a Georgian Revival mansion, formal gardens, and a working farm, reflecting the family’s legacy and love for Vermont.
Enjoy getting lost in the landmark independent bookstore located in Manchester, Northshire Bookstore. This store offers an extensive selection of books across all genres, a dedicated children's book and toy area, and a cozy café. Known for its warm, inviting atmosphere, it frequently hosts author events and book signings, making it a cultural hub for both locals and visitors.
Evening:
Start to head back to Bennington and take scenic route 7A and make sure to stop in Arlington for dinner at Browyn On The Battenkill, a rustic European tavern, dressed up with the treasures from the Chef’s travels including oversized antique chairs and tables. The vibe is Old Europe with a German flair and cozy laid-back Vermont, with ornate woodworking and a warming wood-fire nestled in the rear dining room.
Upon arrive back in Bennington, check out the theater and performing art scene at either Bennington Theater or Monument Arts & Cultural Center (check their websites for a current schedule).
Animal Farm at Merck Forest and Farmland Center
Day 3: Nature Day
Morning:
Head to downtown Bennington for breakfast at The Local - great for coffee, bagels, treats and sandwiches.
Head to the Merck Forest and Farmland Center (40 min from Bennington), a conservation area offering extensive hiking trails, sustainable farming education, and breathtaking views of the Taconic and Green Mountains. Choose trails suitable for your family’s ability levels.
Afternoon:
As you head back through Dorset, Vermont, stop at the Dorset Bakery to pick up some lunch for a picnic lunch at Lake Shaftsbury State Park.
Head 20 minutes south and enter Lake Shaftsbury State Park and spend the afternoon swimming or renting canoes at the park.
Evening:
Drive back to Bennington.
Wash up and grab dinner at Madison Brewing Co., a family-friendly brewpub.
Day 4: Departure and Local Culture
Morning:
Enjoy a leisurely breakfast at The Angry Egg 2 (try out the Angry Egg Sammich)
Stroll through downtown Bennington, visiting local shops and the covered bridges. Don’t forget to get a chocolatie treat for the drive home at The Village Chocolate Shoppe!
Afternoon:
Need a sandwich for the road as well? Check out the recently opened Vermont Chef, full of Boar’s Head meat and other Mediterranean and Middle Eastern treats.
This itinerary blends history, culture, shopping, and plenty of outdoor activities, ensuring that everyone in the family has a memorable long weekend in The Shires of Southwestern Vermont.
Check out various lodging options here!