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CAN'T MISS FALL ACTIVITIES
The Berkshire Botanical Garden's Harvest Festival in Stockbridge, MA is October 11-12. Get ready for the much-anticipated Berkshire Botanical Garden’s annual Harvest Festival, a cherished tradition that has been a highlight of our community since their founding! This year’s festival promises to be a vibrant celebration filled with non-stop family fun! Delight in the delicious offerings from the botanical bakery, featuring mouthwatering sweets, savory chili, and creamy bisque, alongside a lively beer garden and a variety of food trucks. With over 80 craft vendors showcasing their unique creations, an exciting obstacle course for the kids, a massive plant sale for garden enthusiasts, and live music performances to keep your spirits high, there’s something for everyone to enjoy! While they won’t be hosting a tag sale this year, their "Accessorize Sale" will dazzle with a fabulous collection of clothing, belts, scarves, jewelry, and shoes.
The Incredible Naumkeag Pumpkin Show is BACK from October 1-31! This year with more pumpkins, more fun, and an expanded schedule! It's a celebration of autumn with over 1,500 jack-o-lanterns, hundreds of mums, pumpkins and countless gourds. Hot cider and fall treats will be available for sale on-site. Advanced purchase of timed tickets is required and suggested as it does sell out fast.
Visit the Bidwell House Museum in Tyringham, MA on October 4 and 5 with a preview event on October 3 to immerse yourself in the lives of the men and women who lived during America’s Revolutionary War. As you make your way down Art School Road to the Museum, you will be able to leave the modern world behind and enter a time when fire was used for cooking, everyone lived off the land and muskets were the weapon of choice. The living history weekend includes lectures, tactical experiences and artillery demonstrations.
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. Since establishing their farm in 1980, they typically have over 25 varieties of apples, including several heirlooms as well as their own fresh-pressed, all-natural unpasteurized sweet cider blend. |Great Barrington, MA
All aboard! Ride the The Hoosac BERKSHIRE Valley Fall Foliage Trains (Sept 20, 27, October 4, 11, 18) and Halloween Trains (October 25 & 26) |Adams, MA
In addition to the can’t miss fall activities, there’s always LIVE PERFORMANCES AND EXHIBITIONS TO VIEW.
Tanglewood Learning Institute in Stockbridge, MA at the Linde Center for Music and Learning are increasing their programing with over three dozen programs running from early September through May. The season includes a new jazz series, solo and chamber recitals, holiday programming, a film series, and several events for families. TLI Jazz offers the Berkshires Jazz 20th Anniversary Concert with Emmet Cohen and Georgia Heers (Oct. 10), drummer Ulysses Owens, Jr. and his band Generation Y (Nov. 7), the Ted Rosenthal Trio (Nov. 28), and vocalist Stella Cole (Dec. 13).
At the Unicorn Theatre in Stockbridge, MA Berkshire Theatre Group presents Mary Zimmerman’s Metamorphoses, winner of the Drama Desk Award and a Tony Award nominee, dives headfirst into the thrilling, sometimes terrifying world of Greek and Roman mythology September 25 - October 26. At the Colonial Stage in Pittsfield, MA The Eagles Experience takes stage on October 4, The Vagabond Ball on October 17, Yesterday Once More: A tribute to the Carpenters on October 18 and don't miss Albert Cummings performing live on November 14.
Berkshire Bach's Fall Season has begun. On September 20th, Kenneth Weiss, a professor of Chamber music at Conservatoire National Superieur de Musique et de Danse de Paris will perform Harpsichord, Peter Sykes, Harpsichord (Oct. 25), Film Bach & Friends (Nov. 8) and Messiah Sing-Along (Nov. 29).
Norman Rockwell Museum Exhibit Jazz Age Illustration opens November 8, 2025 – April 6, 2026 Jazz Age Illustration is the first major exhibition to survey the art of popular illustration in the United States between 1919 and 1942. Organized by and from the Delaware Art Museum's collection, with selective loans, the exhibition explores the mass visual culture that emerged at the end of the First World War—a period characterized by cultural vibrancy and dramatic social change. Jazz Age Illustration will include more than 100 works of art and dozens of publications by prominent artists such as Aaron Douglas, John Held Jr., Neysa McMein, Norman Rockwell, and Frank Schoonover. On view & continuing I SPY! Walter Wick’s Hidden Wonders Through October 26, Hidden Worlds and Wonders: Outdoor Sculpture Exhibition Through October 26 and Illustrators of Light: Rockwell, Wyeth, and Parrish from the Edison Mazda Collection Through May 10, 2026. |Stockbridge, MA
In October comedian John Blue takes his Berserker Tour to the Mahaiwe Performing Arts Center on October 3. Also performing this Fall at the Mahaiwe will be Pat Metheny, winner of 20 Grammy awards in 10 different categories on October 4, David Sedaris, one of America's Pre-eminent humor writers and a master of satire on October 5 and Folk-rock singer-songwriter Natalie Merchant in an acoustic duo with Erik Della Penna on October 31 and November 1. Over her 40-year career Natalie Merchant has earned a reputation as a songwriter and recording artist of rare quality, a captivating stage performer, and a skilled producer. She has also distinguished herself as a social justice and environmental activist through her work with a wide variety of non-profit organizations, and by creating documentary films and large-scale community arts projects. The Mahaiwe will hold a Grand Opening Celebration for its new performance space the Indigo Room from October 10 through October 12, with performances by jazz vocalist Ann Hampton Callaway, blues guitarist Guy Davis, and family-friendly musician Terry A La Berry, among ceremonial festivities throughout the weekend. |Great Barrington, MA
The great-great-grandson of the literary legend Charles Dickens, British actor Gerald Charles Dickens returns to Ventfort Hall Mansion and Gilded Age Museum, in Lenox, MA this time to present his one-man theatrical performance of his ancestor’s classic works in Mr. Dickens Is Coming! on Sunday, September 21 in both a matinee at 2 pm and an evening performance at 7 pm. An elegant tea will follow the matinee performance. Ventfort will host its second annual Masquerade Macabre on Saturday, October 25th. They also offer daily tours and special ghost tours through their historic estate sharing tales of their hauntings. Stand in the places where the eerie encounters occurred, listen to the first-hand accounts of those who experienced them, and maybe even experience something unusual yourself.
At Shakespeare & Company in Lenox, MA Mother Play by Paula Vogel continues through October 5. The play by Paula Vogel, directed by Ariel Bock follows Phyllis, a hardheaded matriarch, and her children, Martha and Carl, through five apartments and through many hardships, including cockroach infestations and painful conflicts. Phyllis wants her children to follow a certain path, but they each forge their own way. From October 10 -12, Celebrating Jewish Plays will hold an Immersive Weekend of Four Staged Readings: The Price, by Arthur Miller – Friday, Oct. 10, 7 pm, Roz and Ray, by Karen Hartman, directed by Daniela Varon – Saturday, Oct. 11, 2 pm, Featuring Tony-nominated actor John Douglas Thompson (HBO’s The Gilded Age), Here There Are Blueberries, by Moisés Kaufman and Amanda Gronich – Saturday, Oct. 11, 7 pm Featuring Annette Miller (The Victim, Golda's Balcony), The Sisters Rosensweig, by Wendy Wasserstein – Sunday, Oct. 12, 2 pm
This fall The Mount—Edith Wharton’s historic home in the Berkshires—invites visitors to immerse themselves in a dynamic lineup of events that celebrate literature, art, and the supernatural. From spine-tingling ghost tours to captivating dramatic readings, The Mount promises an unforgettable autumn experience for all ages. Wharton on Wednesdays brings Edith Wharton’s short stories to life, performed by acclaimed local actors on the Terrace of the Main House. Arrive early to enjoy refreshments from the Terrace Café as twilight sets the perfect stage. On October 8, 5:30pm – The Triumph of Night read by Tod Randolph. Additionally, don’t miss our Daily House Tours available through October 31, and be sure to join us for Ghost Tours every Friday night in September and October. The Sculpture at The Mount exhibition will also run through October 19, presenting a unique opportunity to engage with captivating local artistry. |Lenox, MA
The Clark Art Institute continues its new series of year-round public installations, Paginations, featuring works drawn from the Clark library’s extensive holdings and curated by members of the library staff. The installations are featured in a newly designed space located in the Manton Research Center’s reading room, just outside the entrance to the Clark’s library and are on view for free during all open hours.
On view September 26 through November 16, Back Bay to the Berkshires: Celebrating 250 Years of Art in Massachusetts looks at some of the artists and artistic innovations associated with the Bay State through their relationships with book illustration, printing, and publishing. This display is held in conjunction with MA250, the Commonwealth of Massachusetts' commemoration of the semiquincentennial of the American revolution, and highlights the revolutionary spirit upon which the state was founded. Get outside and wander their trails. Experience the beauty of Ground/work 2025 as the seasons change. Discover something new in their permanent collection and catch the final days of their summer exhibitions. |Williamstown, MA
Chesterwood is open through October 31 and offers the exhibition Modeling Women Female Artists and Models at Chesterwood and the annual outdoor sculpture exhibition, Global Warming/Global Warning! The exhibition is curated by architect and preservationist Michael F. Lynch, with works by artisit Kathleen Jacobs, Ann Jon, Harold Grinspoon, Natalie Tyler, and DeWitt Godgrey. |StockbridgeMA
The Stockbridge Library presents the Berkshire Players Concert on October 19, the 2025 Annual Pumpkin Walk on October 24 and Alison Larking audiobook launch on October 26. The library offers numerous events, programs for adults and children and free checkout of digital books, magazines and audio books. For a full list on events click here. |Stockbridge, MA
Susan B. Anthony Birthplace Museum Exhibit "Votes for Women: How Tea Sparked a Suffrage Revolution" runs through October 31 . The exhibit centered around an early 20th century “Votes for Women” tea set, donated by Ventfort Hall Gilded Age Mansions & Museum. |Adams, MA
Austen Riggs Center Free Exhibition Making Meaning: Growth and Artistic Expression in the Activities Program at the Austen Riggs Center at the Corner House Community Exhibition Space on 48 Main St, Stockbridge runs through -October 12. |Stockbridge, MA
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