Southern Vermont & The Berkshires Day Trip Itinerary

Experiencing the country drive from Pond Mountain Inn on Routes 30, 7 &7A to southern Vermont and the Berkshires may be one of the prettiest drives in the northeast…

Bennington, Vermont—The Gateway to the Berkshires

The Town of Bennington: After a day of exploration here and beyond, and on your way back to Pond Mountain Inn, first stop in historic downtown Bennington to experience a vibrant cultural scene with lovely sidewalk cafés—it’s quintessential Vermont.

Robert Frost Stone House Museum: South Shaftsbury, VT. Just off Route 7A toward Bennington, the museum captures nice moments of Frost’s life in Vermont. Robert Frost lived here in the 1920s, the Stone House Museum and grounds are a lovely companion to where Frost is buried in Bennington.

The Old First Church: The First Protestant Church in Vermont was gathered in 1762. Early churches of New England hold a special place in our hearts as we’re all drawn to these remarkable New England towns and villages to experience this unique sense of place that broadly defines our New England character. Robert Frost’s grave is located behind the church.

See our blog for the beautiful interior photograph and further insights. 

The Bennington Battle Monument State Historic Site: The spectacular 306-foot stone obelisk was completed in 1889 to commemorate the Battle of Bennington that took place on August 16, 1777, and was considered the turning point of the Revolutionary War. Visitors can explore exhibits on the grounds, and ride the elevator to the top. The area of Old Bennington is pure New England.

Bennington Museum: Explore the rich culture of southern Vermont, eastern New York State, northwestern Massachusetts, and southern New Hampshire in all its forms, from the 18th century to the present. The permanent collection includes superb furniture and paintings from Vermont, one of the oldest “Stars and Stripes” in existence, and a 1924 Martin Wasp Touring Car, the only automobile manufactured in Vermont.  

Park McCullough House: Park-McCullough is one of New England's finest, most significant, and best-preserved Victorian Mansions. It is an actual example of a country house in the Second Empire Style and incorporates architectural features of the Romantic Revival style that was popular then.

Bennington College: Year after year Bennington is recognized by The Princeton Review for campus beauty—inside and out—from its student houses to its 440 acres of sweeping views. And, Architectural Digest included Bennington of its list of the country’s “Top Ten Campuses with Best Architecture.”

Covered Bridges: Silk Road Covered Bridge • Henry Covered Bridge • Paper Mill Village Bridge.

See our Vermont Covered Bridges page for more.  

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Welcome to The Berkshires—Williamstown & North Adams, Massachusetts: We’ll show you the most northern area of The Berkshires—serene mountain vistas, lush forests, and clear blue lakes on your way to unforgettable cultural experiences that you’ll never forget.  

The Clark Art Institute: This museum simply cannot be missed—arguably, one of the finest museums in the world. The Clark’s collection includes; works by Dürer, Degas, Toulouse-Lautrec, Gauguin, Inness, Renoir, Rodin, Goya, Monet, Courbet, Corot, Manet, Sargent, and Homer. The Clark is one of our favorite museums, with an extensive American and English sterling silver collection… the silver is polished every fourteen years. *

Williams College: Walk the campus, and see why Williams College is among the oldest and most prestigious liberal arts schools in the country. Williams does not have any mandatory courses, but it does have rigorous requirements for students in the arts and humanities, social sciences, science and mathematics. 

Massachusetts Museum of Contemporary Art (MASS MoCA): This museum also cannot be missed, even if modern art isn’t your thing. One of the world’s liveliest centers for making and enjoying today’s most evocative art. With vast galleries and a stunning collection of indoor and outdoor performing arts venues, the raw industrial character of the soaring galleries with 250,000 square feet of open and often naturally lit space may be as impressive as the art work itself. *

* Given the depth and breadth of The Clark and MASS MoCA, you may find it overwhelming to visit both museums on the same day—each take over two hours to visit. 

Norman Rockwell Museum: Founded in 1969, the Norman Rockwell Museum is dedicated to the enjoyment and study of Rockwell’s work and his contributions to society, popular culture, and social commentary. The Museum houses the world’s largest and most significant collection of Rockwell’s work, including 998 original paintings and drawings. Rockwell occupied some 20 studios during his life, but it was the last one—on the museum grounds—he called his “best studio yet.”

Mount Greylock: The 3,489-foot mountain located in the northwest corner of Massachusetts is the highest point in the state, and from its peak on a clear day, you can see as far as 90 miles away. In the mid-19th century, many writers and artists were drawn to Greylock—Nathaniel Hawthorne, William Cullen Bryant, Oliver Wendell Holmes, Herman Melville and Henry David Thoreau. Hiking trails at Mount Greylock vary in difficulty from casual to extremely difficult.