Small Town America: Stockbridge, Massachusetts

Visit an American Art Colony in the Berkshires

The small town of Stockbridge, Massachusetts, located in the Berkshires, is a four-season destination filled with cultural attractions, outdoor recreation, world-class performing arts, and unique dining and shopping experiences. Stockbridge is best known as an art colony and the former home of American artist Norman Rockwell and sculptor Daniel Chester French. A wide range of outdoor activities are available, from hiking trails, cycling, and bird watching in the summer to skiing and snowshoeing during the winter months. The historic village of Stockbridge is a perfect representation of small-town America with historic lodging, galleries, shops, and restaurants to explore during your visit.

Did You Know? A resident and former slave living in Stockbridge played a role in ending slavery. Elizabeth Freeman’s “freedom lawsuit” served as a precedent to future cases that would eventually end slavery in Massachusetts. Ms. Freeman was laid to rest, a free woman, in the Stockbridge Cemetery.

Events & Festivals

Plan your trip around one of the major festivals that take over Main Street. The Summer Arts & Crafts Show held in August has over 80 jury-selected artists and crafters. The Halloween Parade & Party features dozens of family activities. The Stockbridge Main Street at Christmas event is your chance to celebrate with the locals and experience the village decorated for the holidays. You might be familiar with Rockwell’s rendition— this is your chance to see it for yourself!

Museums & Attractions

– The highlight of any art enthusiast’s visit to the Berkshires is the Norman Rockwell Museum. See the world’s largest collection of original Rockwell art and step into Rockwell’s actual art studio, presented as it would have appeared when the artist was alive. Each visit to the museum is different with frequent rotating exhibits.

– Another not-to-be-missed art museum in Stockbridge is Chesterwood, the former country home, studio, and gardens of American sculptor, Daniel Chester French. French might not be a household name, but his masterpieces include the Minute Man (Concord, MA) and the Abraham Lincoln statue in the Lincoln Memorial (Washington, D.C.).

– Spend a day touring historic homes, covering almost 300 years of American history. Take a step back in time at the Mission House, a rare surviving Colonial-era mission house. The Federal Style Merwin House was a summer retreat for the Doane family and is decorated with American and European furniture and objects from their travels in America and abroad. The Naumkeag House and Gardens is a Gilded Age 44-room mansion and 10-acre garden that is definitely worth a visit. The home was owned by Joseph Choate, a leading 19th-century attorney, and designed by the renowned architectural firm of McKim, Mead, & White.

Outdoor Activities

– Between May and October, the Berkshire Botanical Gardenis a great outdoor option while visiting Stockbridge and the Berkshires. The 15-acre public garden features 25 display gardens areas showcasing local plants. Every year the Garden’s Harvest Festival is held over Columbus Day weekend. The popular autumn event features children’s activities, pony and hayrides, games, live entertainment, over 100 regional artisan vendors, a farm market, and yard and plant sales throughout their final weekend of the season.

– From your home base in Stockbridge there are dozens of hiking trails and places to bike along country roads without much traffic. For miles of trails and wildlife viewing, Mass Audubon’s Pleasant Valley Wildlife Sanctuary is a great choice. Greylock Glen has a trail system that covers 1,000 acres. If you are feeling ambitious, hike to the top of Mount Greylock, the tallest point in Massachusetts.

– During the fall, take a hot air balloon ride for an amazing view of the changing foliage. The winter months are fantastic for Nordic skiing or downhill runs at Ski Butternut or Berkshire East Ski Resort.

Historic Downtown

The downtown village is worth exploring, including the former stagecoach stop and colonial meeting place – The Red Lion Inn. Take a step inside, have a seat on the porch, and enjoy lunch in the garden. There aren’t many of these historic hotels left in operation, so have a look around and enjoy it. The hotel has hosted U.S. Presidents, American authors, movie stars, and musicians.