Celebrate music, movement, and cultural traditions at the 17th annual Tamarack Hollow Berkshire Drum and Dance Fest on Oct. 17 in Windsor! Enjoy West African drumming, interactive dance, and community performances. ow.ly/rqM050ZXkSg

Ready for winter in the Berkshires? Jiminy Peak’s last chance to save on 2026/27 season passes is Oct. 15. KidsRule Mountain Camp and Value Cards are on sale, too. Plan ahead: jiminypeak.com/

What's calling you to the Berkshires this October? 🎃 Our latest newsletter is packed with October inspiration, seasonal favorites, and scary-good ways to make the most of fall #intheBerkshires. ow.ly/SjJC50ZWios

Lenox Restaurant Week! November 1–8, local restaurants will offer special prix fixe menus, tasting menus, family-style feasts & more. Participating spots include Ombra, Frankie’s, Brava, Firefly, Cello, Pizzeria Boema and more. #intheberkshires #TasteBerkshires

The inaugural Stockbridge Film Festival comes to the Berkshires October 16–18! Expect short films, documentaries, narrative features, filmmaker Q&As, industry panels, networking, and an awards program, plus a panel with Oscar winner Cynthia Wade. simpletix.com/e/stockbridge-…

Ready to put your music knowledge to the test? Music Bingo is coming to the Pittsfield Italian American Club on Thursday, October 8, from 5–8 PM! Join Berkshire County Head Start for a fun night of music, bingo, and community. Register here: zeffy.com/en-US/ticketing/be…

🍂 Berkshire Botanical Garden's Harvest Festival returns October 10–11, 10 a.m.–5 p.m. Pony rides, hay bale maze, live music, square dancing, scarecrow walk, petting zoo, craft vendors, hot cider, autumnal bisque, pies & more. Kids 12 & under get in free! berkshirebotanical.org/harve…

“Western Mass is home to unique attractions, museums, sporting experiences, outdoor adventures, cultural events, restaurants, and four-season activities.” A look at what makes the region a four-season destination. Source: explorewesternmass.com/ Photo Cred: Great Sky Media

🎭 Local actors, this one's for you! Berkshire Theatre Group is casting local non-Equity actors for A Christmas Carol. Auditions are Oct. 19, with youth auditions Oct. 20. Sign up by Oct. 10 [email protected] #intheberkshires #Berkshires

🚨 Parade Day reminder! Heading to the 70th Annual Fall Foliage Parade Sunday, Oct. 4? No parking begins at midnight, with traffic changes starting at 10:30 AM and all detours/closures in place by noon. Plan ahead + allow extra travel time. 🍂 1berkshire.com/fall-foliage-…

🍂 Heading to the 70th Annual Fall Foliage Parade Sunday? Traffic detours + road closures begin Sunday morning, with all parade-route closures in place by noon. Plan ahead: 1berkshire.com/70th-annual-f… See you at 1 PM! 🍁

This weekend in the Berkshires: The Homelands PowWow – Tending the Fire returns to Shakespeare & Company in Lenox, Oct. 3–4. Experience traditional dancing, drumming, storytelling, Native arts, food & cultural education. $20/day or $30 weekend pass. homelandspowwow.org/tickets-…

Where is your favorite place pick pumpkins? We suggest Hilltop Orchards🍎with famous cider doughnuts, Ioka Valley farm 🍁 with delicious maple syrup, Bartletts Orchard for friends in Richmond, and Whitney's Farm Market for their corn maze and baby animals! 🐑 🍂

Celebrate Hispanic Heritage Month through dance with Jacob’s Pillow. Explore a new playlist featuring Latine artists from the Pillow’s history, plus a new podcast with Festival 2026 artists Eduardo Vilaro, Nélida Tirado, and Luis Salgado. Explore more at jacobspillow.org

CATA’s Reading of Poetry & Prose brings together writers with disabilities for an intimate evening of heartfelt, thought-provoking, poignant, and humorous work, read by a cast of guest readers. 9/29 5–7 PM The Stable at The Mount in Lenox Learn more at cataarts.org.

Making Marks by Berkshire artist Caroline Kelley opens October 2 at Framework by Downtown Pittsfield, Inc. Join the opening reception from 5–7 PM at 437 North Street. The exhibition will be on view through October 29. Learn more at downtownpittsfield.com.

A behind-the-scenes look at the Berkshire Food Project getting their Fall Foliage Parade float ready! 🍂 See it in motion Oct. 4 at 1 PM in North Adams during the 70th Annual Fall Foliage Parade. 1berkshire.com/fall-foliage-…

A new story is taking the stage in the Berkshires. 🪐 Barrington Stage Company presents the world premiere of The Urmetazoan, Sept. 30–Oct. 25 in Pittsfield. Plan a fall night at the theater. #intheberkshires #Berkshires #BerkshireTheater barringtonstageco.org/series…

PMC Unpaved returns October 3! 🚴🍂 Ride 20, 30 or 50 miles through the scenic gravel backroads of the Berkshires, then enjoy a full weekend at Camp Mah-Kee-Nac in Lenox. #intheBerkshires #PMCUnpaved unpaved.org/

Tune in Wednesday at 7:30 PM! 🎨 Andrew DeVries of DeVries Fine Art International will be featured on WMHT PBS’s A House for the Arts, highlighting Berkshire-based artistry and creativity. #liveBRK #intheberkshires