What to Do on a Weekend Getaway in Stockbridge, MA

If you're one to embrace the chill and send summer away at the start of September, you’re not alone. In the western most of Massachusetts, you’ll find a little town that celebrates the season of pumpkins, spookiness, and cozy sweaters. Known for its fall foliage and wide range of outdoor activities, Stockbridge is quaint, authentic, and the perfect balance of adventure and relaxation. In short, it may be something in the air, but this part of the Berkshires has a unique charm you won’t want to miss. 

Things to Do in Stockbridge, MA

Berkshire Botanical Garden 

There’s no shortage of things to do in the Berkshires. One of our fall favorites is the Berkshire Botanical Garden, a not-for-profit, membership-supported educational organization that spans 24 acres. Established in 1934 as the “Berkshire Garden Center,” today it’s known as one of the oldest public display gardens in the Northeast. They host year-round classes, lectures, workshops and, of course, garden exhibits. Here, every visit promises discoveries. 

Chesterwood 

American sculptor Daniel Chester French may be best known for creating two of our nation’s most powerful symbols: the Minute Man at the Old North Bridge in Concord, Massachusetts and Abraham Lincoln for the Lincoln Memorial in Washington, D.C. But, his inspiration stemmed from right here in the Berkshires. A visit to Chesterwood—his former summer home, studio, and gardens where he did much of his work—perfectly fuzes culture, history, and art. 

Afternoon Tea 

If you’ve ever been to England, you know afternoon tea is more than a social hour. Served on Fridays and Saturdays from 4pm to 5pm at The Red Lion Inn, afternoon tea invites you to enjoy a variety of Harney & Sons loose leaf teas, delectable finger sandwiches, and sweet bites on the Side Piazza, Front Porch, Main Lobby, or Side Parlor. 

Norman Rockwell Museum 

Located right in Stockbridge, Norman Rockwell Museum is a place for learning as well as appreciating and preserving art. Inspired by the legacy of iconic painter and illustrator Norman Rockwell, the Museum features the world’s largest and most significant collection of Rockwell’s work as well as rotating exhibitions.  

The Lion’s Den

Tucked away under Red Lion Inn, The Lion's Den is a speakeasy-esque bar that serves up more than just specialty cocktails. Live music, brought to you by local bands, jazz musicians, and more, is hosted regularly, as are special and seasonal events. So grab a seat, sip a drink, and enjoy this unbeatable Berkshire activity. 

Tanglewood 

Iconic Tanglewood is home to the Boston Symphony Orchestra, bringing classical musicians,orchestras, and contemporary artists to the area. Year-round, they host unique events such as masterclasses, open rehearsals, lecture series, concerts, and more. Be sure to check out their Berkshire events this weekend—you're bound to find something that suits your fancy.

Places to Eat in Stockbridge, MA

The Dining Room at Red Lion Inn

The menu at the historic Main Dining Room at the Red Lion Inn features a blend of traditional favorites and contemporary interpretations of classic New England fare. Here, the chefs believe that the highest quality ingredients have the power to change an entire dish. Ideal for a romantic date night or special occasion, The Main Inn has an award-winning wine selection and an artisanal cocktails and beer program. 

Widow Bingham’s Tavern

Craving fresh vegetables and seasonal staples? Named for Anna Bingham, one of Red Lion Inn’s original owners, this rustic tavern offers traditional favorites and updated classics like lobster rarebit, coconut curry mussels, and gnocchi parisienne. Prepare to indulge in a hearty meal in a cozy and eclectic setting adorned with historic signs, old posters, wicker baskets, and a hodgepodge of other memorabilia.

Stay at The Red Lion Inn

There are so many things to do in the Berkshires in the fall! Make The Red Lion Inn your Stockbridge homebase this weekend as you explore all that the quaint town has to offer. The quintessential Berkshire hotel, The Red Lion Inn, has been a landmark of hospitality for 250 years and has grown and evolved with new generations of guests. The best of the Berkshires awaits—book your room now.