Theatre, Art and Fall Foliage

Set amidst the scenic fall foliage of Vermont and the Northern Berkshires in September and October, this is a typically shorter trip that offers picturesque views and cultural exploration. From quaint and delightful Vermont inns to some of the most respected art museums in the world, this is the very best way to experience the autumn color changes in New England. Landmarks include the Clark Art Institute, Mass MoCA, the Weston Playhouse, scenic walks along trails and covered bridges, and much more.

In addition to hearty strolls each day across several of New England’s most picturesque towns, followed by classic New England drinks and dinners on cool fall evenings in front of roaring fires in big stone fireplaces, our travellers typically attend two plays in three nights, each showcasing a different theatre company’s approach to both new and traditional performances. You can choose from Vermont’s oldest and longest-running professional theatre company, the Weston Playhouse, which offers the best theatre in Vermont, a performance by the Oldcastle Theatre Company, opened almost fifty years ago, or a play at the Dorset Playhouse, the historic barn turned theatre that has been around since 1927 and is a staple of New England theatre. 

The Northern Berkshires is also home to two elite museums that range from French impressionist galleries to massive contemporary art installations. Opened to the public the decade following World War II, The Clark has become one of the most beloved and respected art museums in the world, and our travelers continue to find it a treasure each time they go here. It is perhaps best known for its significant collection of French Impressionist and Post-Impressionist paintings by such recognized artists as Pierre-Auguste Renoir, Claude Monet, Edgar Degas, Eduoard Manet, Henri de Toulouse-Lautrec and Camille Pisarro.

The Clark is one of the premier art museums in the country, with stunning galleries on a scenic property.

On the complete other end of the art spectrum, MASS MoCA, only opened in 1999, is one of the world’s ‘liveliest centers for making and enjoying today’s most evocative art.’ Located in an enormous repurposed factory, MASS MoCA embraces all forms of art: music, sculpture, dance, film, painting, photography, theatre and new, boundary-crossing works of art that ‘defy easy classification.’ It is sure to keep your attention.

In addition, the Williams College Museum of Art has blossomed over the past two decades to become a must-see for art tourism in the Berkshires. 

Experiencing great destinations also means experiencing the natural beauty of New England. From trail walks and garden tours to more demanding hikes, the Berkshires and Vermont not only share a border, they share similar terrain. Prospect Rock Trail, part of the Green Mountain National Forest, provides a family friendly 3+ mile hike that features, babbling mountain streams and beautiful summit foliage views. For a more vigorous outing, and the most scenic view of fall foliage from the tallest peak in the state of Massachusetts, there is a choice to hike or drive up to the summit of 3,491 foot Mount Greylock. We provide guides or drivers if you desire.

While you won’t be spending too much time in your inn, we ensure that each place we stay is special and has top-notch relaxation space. From rocking chairs on a front porch, to spacious living rooms, you will have the opportunity to relax, enjoy a drink and take in the environment of each destination.

What a wonderful adventure for a few days with good friends or family. Maybe ones you haven’t seen in awhile!