Stockbridge has a small, attractive downtown surrounded by some lovely historic homes. The small town, with a population of approximately 2018 people, has had a large influence on American art. I recently went back for the second time in July 2026. Highlights of my visits include:
The Red Lion Inn: At 30 Main St., this is an inn, one of the oldest in the US, that has been providing food and lodging since 1773, when it began as a two-story tavern. After a fire in 1896, it was totally rebuilt. I love the charming atmosphere of this historic building. I enjoyed a fun lunch in Widow Bingham’s Tavern. They have a more formal main dining room, a lovely outdoor patio in the courtyard and the Lion’s Den Pub downstairs, dating from 1937, that is open in the evening. In addition to dining they have 125 antique-filled guest rooms and suites. The long front porch with rocking chairs is out of a different era. Past guests have included Presidents Grover Cleveland, William Howard Taft, Theodore Roosevelt, Calvin Coolidge and Franklin Roosevelt; and literary figures including Nathaniel Hawthorne, Henry Wadsworth Longfellow and Thornton Wilder.
Located within the Stockbridge General Store is the Main Street Cafe: This is a casual downtown cafe serving breakfast and lunch along with coffee and ice cream. I stopped in for some ice cream before heading back to Hudson, NY. 40 Main St.
Stockbridge General Store is a mall store offering grocery items along with home decor, gifts, old-fashioned candy along with children’s puzzles and toys.
For more sweets you might check out The Lost Lamb Patisserie for French and Berkshire-inspired croissants, tarts, cupcakes, macarons and baguette sandwiches. They also serve coffee drinks. 31 Main St. There is also Peace, Love and Chocolate which is a local shop offering handmade chocolate and truffles along with coffee drinks and gelato. I was sorry that both were closed on the day that I was back in town. It is located in the Mews at 36 Main St.
Norman Rockwell Museum: Located at 9 Route 183, not far from downtown Stockbridge, this is a museum highlighting the work of this famous illustrator. Here you can see his studies for his original paintings for many of his famed Saturday Evening Post covers. Downstairs, you can see all of his covers in one exhibit. They also have temporary exhibitions of other artists. His original Stockbridge studio which was downtown behind his home was moved to the 36-acre site. This is a highlight so make sure to see it as it is a short walk from the museum.
Just south of the Norman Rockwell Museum is Chesterwood, a Site of the National Trust for Historic Preservation. Chesterwood is the former Summer home, studio and gardens of Daniel Chester French, one of America’s foremost sculptors, who lived from 1850 to 1931. He is best known for his Minute Man statue from 1875 in Concord, MA and his statue of a seated Abraham Lincoln, from 1922, that is the focal point of the Lincoln Memorial in Washington, D.C. He created over 100 memorials and monuments located in France and the US.
You can tour his home and visit his studio where he did most of his work. Since 1978, more than 500 emerging and established sculptors have exhibited at Chesterwood. I enjoyed an excellent exhibition of 24 contemporary works located throughout the grounds and gardens. Make sure to check the website to see information about current exhibitions. 4 Williamsville Rd. in Stockbridge, MA.
If you have time, you might visit the Berkshire Botanical Garden at 5 W. Stockbridge Rd., with 15 acres of display gardens featuring perennials, annuals, ornamental grasses, shrubs and trees. There is an herb garden from 1937, a rose garden, a rock garden and a water garden.
Local friends recommend the Berkshire Theatre Group for its good performances. You can choose from performances in Stockbridge at The Berkshire Theater Festival Campus or in Pittsfield at the Colonial Theatre/Garage.
Getting great reviews as a place to stay in town is the Inn at Stockbridge at 30 East St. It has beautifully decorated rooms. It is located in a classic Georgian-style mansion built in 1906 as a private residence.