Nestled in the heart of New England, The Shires of Southwestern Vermont offer a charming and picturesque destination for a family vacation. With its rolling hills, historic villages, and a plethora of family-friendly activities, this region promises a delightful experience for both parents and children. To ensure a memorable and hassle-free trip, we've curated a 3-day itinerary guaranteeing top-notch service and authentic local experiences for your family.
Day 1: Arrival and Exploration of Bennington
Morning:
Arrive in the town of Bennington and check-in at a family-friendly hotel or charming bed and breakfast.
Start your day with a hearty breakfast at a local diner (recommended: Blue Benn Diner, The Coffee Bar, The Angry Egg 2, Elm Street Market, The Local), serving Vermont's famous maple syrup-infused delights.
Mid-morning:
Head to the Bennington Museum, where your children can learn about the region's rich history through interactive exhibits. Don't miss the "Grandma Moses Schoolhouse" exhibit, perfect for younger visitors.
Lunch:
Enjoy a picnic lunch at the picturesque Lake Paran, surrounded by lush greenery and tranquil waters. We suggest these great North Bennington places to pick up your picnic: Powers Market, Prospect Coffee House, or Kevin’s.
Afternoon:
Take a scenic drive to the historic Battle of Bennington Monument and take a ride to the top of monument. Take a moment to reflect on the battle that was the turning point of the Revolutionary War.
Dinner:
Savor a delicious farm-to-table dinner at one of the local eateries, like the Mt. Anthony Country Club (open to the public), serving fresh, locally sourced ingredients.
Day 2: Exploring Manchester and Dorset
Morning:
Travel to the charming town of Manchester and indulge in a scrumptious breakfast at a cozy café or diner:
Mid-morning:
Visit the Northshire Bookstore, where your children can immerse themselves in a vast selection of books, toys, and interactive storytimes.
Late morning:
Embark on a adventure driving up the ambitious Equinox Skyline Drive. The 3,848-foot summit of Mount Equinox is enveloped in a nearly-perpetual breeze that has been described as “nature's white noise.”
Lunch:
Enjoy a delightful lunch at the Zoey’s Double Hex, known for its kid-friendly menu and relaxed ambiance.
Afternoon:
Head to Hildene, The Lincoln Family Home, where the Lincoln family stayed in the summers. Your family can explore the historic mansion and its beautiful gardens. Don't miss the opportunity to take a look at an old-fashioned 1903 wooden Pullman palace car, Sunbeam.
Dinner:
Relish a sumptuous dinner in Dorset at a restaurant like the Barrows House, The Dorset Inn, Mistral’s at Toll Gate.
Day 3: Adventures in Arlington and Shaftsbury
Morning:
Travel to Arlington and begin your day with a delicious breakfast at The Arlington Inn.
Mid-morning:
Visit the Sugar Shack, where your children can learn about the maple syrup-making process and indulge in maple-flavored treats. Discover the fascinating history of the Norman Rockwell Exhibition, boasting a collection of Rockwell's iconic artwork.
Late morning:
Bring your bathing suit and take a dip in the famous Dorset Marble Quarries. The first marble quarry in the U.S., opening in 1785, the beautiful Dorset Marble Quarry is filled with fresh, clean water year-round. The quarry supplied marble to the New York Public Library, Brown University’s library, several impressive mansions in NYC, and the Memorial Continental Hall of the Daughters of the American Revolution in Washington, D.C. With many cliffs to jump from, this has become a trendy and well-known local swimming place. Located at 1848 Vermont Route 30 in Dorset, VT, the quarry is generally open from 9:00 am through dusk, Memorial Day through Columbus/Indigenous People's Day.
Lunch:
Stop at the deli at H.N. Williams and enjoy a picnic lunch at the picturesque Lake Shaftsbury State Park, offering a serene setting for relaxation.
Afternoon:
Finish the day with a stroll in downtown Bennington boasting many fun shops for children including the Village Chocolate Shoppe, Knapps, Gamers’ Grotto, The Gift Garden, various antique stores, and pocket parks.
Dinner:
End your vacation on a high note with a special dinner at a restaurant like The Publyk House, serving up classic Vermont dishes with amazing sunsets.
A family vacation to The Shires of Southwestern Vermont is a wonderful opportunity to create lasting memories with your children. From historical museums to outdoor adventures, this enchanting region offers a diverse range of experiences for the whole family. By relying on Southwestern Vermont Chamber of Commerce members, you can rest assured that your journey will be filled with warmth, hospitality, and authentic local charm throughout your 3-day adventure.