CAN'T MISS FALL ACTIVITIES

The Berkshire Botanical Garden's Harvest Festival returns October 10–11 for a weekend celebrating the best of autumn in the Berkshires. Enjoy 50 artisan craft vendors, regional food trucks, live music, and family-friendly activities including hayrides, a hay maze and jump, pony rides, face painting, a petting zoo, square dancing, and more. The Garden’s 24-acre grounds make a beautiful setting for this much-loved fall tradition in Stockbridge.

Berkshire Coaching Weekend rides again on October 10-12. Experience a step back in time as elegant antique horse-drawn coaches travel through the picturesque towns of Stockbridge, Lenox and Lee, continuing the Gilded Age tradition of coaching in the Berkshires. Visitors are invited to see the beautifully restored coaches and teams of horses as they travel the countryside, with opportunities to view them at the Mount, Highlawn Farm and along the roads through Stockbridge and Lenox.

The Incredible Naumkeag Pumpkin Show is BACK from October 1-31! More than 1,500 jack-o’-lanterns, hundreds of mums, pumpkins and countless gourds transform the gardens into a spectacular celebration of autumn. Timed tickets are required and should be purchased in advance. |Stockbridge, MA

Another family fun activity is the tradition of APPLE AND PUMPKIN PICKING at Windy Hill Farm, located just a few miles south of Main Street, Stockbridge. The farm has been a local fall tradition since 1980, offering apples, pumpkins and fresh-pressed cider. Check with the farm for current 2026 picking availability. |Great Barrington, MA


Celebrate fall at the first annual Sheffield Fall Festival, Saturday, October 17, on the Sheffield Town Green. From 3–7 p.m., enjoy live music, vendors, activities and demonstrations, a costume parade, cook-off and bake-off, and a Jack-o’-Lantern contest and lighting. The celebration continues with Festival After Hours from 7–9 p.m., featuring bonfires, music, entertainment, and refreshments on the lawn behind Dewey Hall and Roberto’s Pizza. Free and open to all!

All aboard! The Hoosac BERKSHIRE Valley Explorer  offers Fall Foliage Speedliner rides beginning September 19, Chilling Tales on Mysterious Rails October 17, and Halloween Rides October 31. Pumpkin Patch Rides and Halloween Trains are also planned. |Adams, MA

Raise a glass to fall with Nejaime’s Wine Cellars! Enjoy an Oktoberfest Free Tasting & Sale on September 19 in Stockbridge and Lenox, featuring fall brews, German and Austrian wines, spirits, cocktails, and bites. On September 30, BRAVA in Lenox hosts a special Sicilian Wine Dinner featuring the wines of Tasca d’Almerita. Explore the wines of the Pacific Northwest at a Wine Seminar at Ventfort Hall on October 8. Then, on November 7, celebrate the season with Nejaime’s Savor the Season Free Tasting & Holiday Sale, featuring fine wines, artisan spirits, gourmet cheeses, and specialty foods.

In addition to the can’t miss fall activities, there’s always LIVE PERFORMANCES AND EXHIBITIONS TO VIEW.

At the Unicorn Theatre in Stockbridge, MA, Berkshire Theatre Group presents Summer, 1976 by Pulitzer Prize-winning playwright David Auburn October 7–31. The production explores friendship, memory and the unexpected ways one summer can shape two lives. At The Colonial Theatre in Pittsfield, An Evening with David Sedaris takes the stage October 1 at 7:30 p.m. The bestselling author and humorist brings his signature sardonic wit and keen observations to an evening of stories, humor and insights into everyday life. 


Tanglewood Learning Institute at the Linde Center for Music and Learning continues its year-round programming this fall. October highlights include Ulysses Owens Jr. and Generation Y on October 16, TLI Chamber Concert and Radu Rățoi on October 18 and 23, and Andy Wrba & Friends October 30. November brings Berkshire Pulse November 1, Berkshire Bach’s Eugene Drucker: The Savior November 7, Christine Andreas November 13, Imani Winds November 15, Lam Dance Works November 21, and Ted Rosenthal Quartet November 27. | Stockbridge, MA

This fall, Jacob’s Pillow presents two exciting weekends of dance. Youth America Grand Prix: Fresh Voices in Dance, October 16–18, features six rising choreographers and six world premieres, showcasing the next generation of choreographic talent. Doug Varone and Dancers, October 23–25, celebrates the company’s 40th anniversary with a program of kinetically thrilling and emotionally resonant works by acclaimed choreographer Doug Varone. |Becket, MA

At the Mahaiwe Performing Arts Center fall highlights include the Nicole Zuraitis Quartet October 3, Met Opera Live in HD: Così fan tutte October 4, VOCES8 October 9, Raul Midón October 10, Vitamin String Quartet & Girl Named Tom October 16, A.J. Croce October 23, and Jeff Tweedy Solo October 30. November brings Close Encounters With Music: Saluting the Clarinet November 1, Samantha Bee November 13, and the Cowboy Junkies November 14. |Great Barrington, MA

At Shakespeare & Company in Lenox, the fall season continues with The Norwegians through October 4, followed by Celebrating Jewish Plays, October 9–11, featuring a weekend of staged readings and special programming. 

And don't forget Berkshire Bach. On October 10, acclaimed harpsichordist Peter Sykes performs music for harpsichord and clavichord at the Berkshire Waldorf High School in Stockbridge. On November 7, Berkshire Bach joins Tanglewood Learning Institute for The Savior, a book reading and live performance with violinist Eugene Drucker. |Stockbridge, MA

Chesterwood is open through October 31 offering visitors the opportunity to explore Daniel Chester French’s historic home, studio, gardens and woodland trails. The 2026 season features The Minute Man: Examining Patriotism, Victory and Loss and the 48th annual outdoor sculpture exhibition, In the Open: New England Sculptors Reclaim the Landscape. A special Chesterwood 5K Run/Walk will take place October 10. |Stockbridge, MA



At the Norman Rockwell Museum American Stories: From Revolution to Rockwell continues through October 26, while Norman Rockwell Paints the Presidents remains on view through December. Beginning November 7, George Herriman, Krazy Kat, and the Path to Calvin and Hobbes opens, followed by Exploring Calvin and Hobbes and Norman Rockwell: The Human Touch on November 14. The museum’s annual Many Lights, One Season: A Holiday Celebration opens November 20. Historic Studio Tours continue through November 7. A Special Fall tour will take place on Indigenous People's Day Weekend Ocotber 10 & 11. The tour highlights the artwork of Native American artists, such as Shonto Begay, Jaune Quick-to-See Smith, Rabbett Before Horses Stickland, Kay Walkingstick, and more, featured in the Museum's American Stories: Revolution to Rockwell exhibition. The tour will explore how artists explore the complexities of Indigenous identity, myth and history, and cultural resilience.|Stockbridge, MA

Fall brings a lively calendar of programs to the Stockbridge Library Museum & Archives, including the 29th Manhattan Short Film Festival and a series of engaging author talks. Featured programs include Bordeaux Chronicle with photographer Peter Aaron and wine expert Jane Anson on October 16; Tom Rosenstiel in conversation with Marty Baron, discussing The Next Journalism, on October 17; and Linda Kaye-Moses, presenting The Argentera and the Tales of the Six Arabesques, on October 24. The season also includes poetry, book discussions, children's programs, and the annual Stockbridge Town Parade and Pumpkin Walk on October 30. |Stockbridge, MA

Visit the Bidwell House Museum in Monterey on October 3 for a Walk Through History, and explore the museum’s 194-acre grounds, gardens and trails. The museum’s 2026 season continues through October.

The Clark Art Institute  in Williamstown offers another wonderful fall destination. An Exquisite Eye: Introducing the Aso O. Tavitian Collection continues through February 21, 2027, while Giorgio Griffa: Paths in the Forest and Ground/work continue through October 12. On October 12 Indigenous Peoples’ Day Tour: Edmonia Lewis — explores the life and work of the important Black and Indigenous sculptor, using the Clark’s recently acquired Sleep as a starting point and on Performing Artists in Residence Concert featuring pianist Jeewon Park and cellist Edward Arron with guest artists on October 18. The Clark’s extensive grounds and walking trails are also a beautiful way to experience the changing season.

Frelinghuysen Morris House & Studio in Lenox is open weekends to Columbus Day. Visit the home of American Abstract Artists George L.K. Morris and Suzy Frelinghuysen, set on a 46-acre estate. View their paintings, frescoes, and sculpture; experience their exquisite collection of American and European Cubist Art.

The Mount Edith Wharton Cultural Center in Lenox in continues to offer tours, exhibitions, and special programming into the fall. Highlights include local author Betsy Smith celebrating the launch of Sign of a Loon on September 27, and the Whose Truth? Writers and Readers Forum on October 4. The outdoor sculpture exhibition Flourish continues through October 24, along with Roman Fever, From Page to Stage and Robert Oakes’ Among the Primeval Shadows: Exploring the Strange Magic of Edith Wharton’s Ghost Stories on October 16 and 24.

Susan B. Anthony Birthplace Museum in Adams welcomes visitors through October 31, with guided tours of the home where Susan B. Anthony was born and spent her early childhood. The final Afternoon Tea Party will take place on October 31st at 3 p.m.

Step into the Gilded Age—and a little bit of the supernatural—this fall at Ventfort Hall Gilded Age Mansion & Museum in Lenox. Explore the historic mansion and enjoy a season filled with intriguing talks, ghost tours, and Halloween festivities. Robert Oakes, author of Ghosts of the Berkshires, leads evening ghost tours in September and October. On October 24, don your finest masquerade attire for the Masquerade Macabre, an evening of music, dancing, drinks, and dark delights. For those looking for an extra dose of the paranormal, a special Halloween-night investigation takes place October 31.

Fall is also the perfect time to simply slow down and enjoy Stockbridge and the surrounding Berkshires. Take a scenic drive, hike the trails, explore historic Main Street, browse unique shops, enjoy locally sourced dining and experience the brilliant colors of autumn.

Come and stay in our quintessential New England town! Plan a weekend escape or an extended getaway and discover why fall in Stockbridge and the Berkshires is so special.

Start your visit at StockbridgeChamber.org.