10/29/2026
October in the Berkshires: Peak Foliage & Halloween Magic! 🍂
✨ Check out big spots celebrating the season like Naumkeag and Hancock Shaker Village for outdoor beauty, plus The Mount and Ventfort Hall for spooky tours! Our local farms—Highlawn, Windy Hills, Taft, Second Drop, and Hilltop—are always providing the best of the season.
The Naumkeag Pumpkin Show goes through month-end (get tickets online in advance!).
Swipe through for events, music, art, food, shopping, and hiking!
And stay with us next time: use code WEEKDAY15 for 15% off weekdays in Fall.
www.berkshirehousestay.com
Link in bio too to book direct! 🏡
✨ Events & Entertainment: From outdoor fun to spooky entertainment, here is what's happening:
• Wknd: Hancock Shaker Village Haunted Hancock
• 10/30: The Mount Ghost Tour (Kids & Adults)
• Wknd: WAM / Shakespeare & Co. Camp Siegfried
• Wknd: Naumkeag Pumpkin Show (book ahead!)
• 10/31: Norman Rockwell Walking Tour
• 10/31: Ventfort Hall Paranormal Investigation
• Wknd: Unicorn Theatre Summer 1976
🎸 Live Music ( ): Always good music vibes in the Berkshires. Here is our recommendation this week:
• Route 8 Pub: Rounders Revival (Fri)
• Stationary Factory: Bad Company Tribute (Fri)
• Lion’s Den: Miss Paula / Twanbusters (Fri)
• Balderdash Cellars: Colby Lewing (Sat)
• Buttonball Barn: Halloween Bash (Sat)
• Barrington Hall: The Weeds (Sat)
• Lion’s Den: Michael Junkins & Friends (Sun)
🍴 Good Food ( ): We enjoy so many different spots in the Berkshires. Some fancy, some hearty, some great breakfasts!
• Lee (Walkable from BHS): The Station (dinner at bar), Agave Mexican, Burmese Bowl
• Egremont: The Mill (modern fare)
• Lenox: Cello (seasonal), Ombra (eat 'til midnight)
• Great Barrington: Bizen (Omakase), Number 10 (Steak & Martini)
🛍️ Shopping ( ): When you are staying with us, here are the cool shops in Lee. You can walk to all but the Mall! Enchanted Alter, Finders Keepers, Ben’s, Knollwood Antiques, Zabian's, and the Outlet Mall. Plus, grab charcuterie board items at Highlawn Farm!
🎨 Art ( ): So much to see. These are some of our favorite places to stop—some indoors, some outdoors:
• The Wit: Mood Swings by Michael Alfano (All Wknd)
• Good Purpose Gallery: Addicted to Abstract (All Wknd)
• Art on Main: Plein Air Show (Sat)
• Ozzie’s Glass Gallery (All Wknd)
• Art in Berkshires Gallery: Visual Frequencies (All Wknd)
• Bernay Fine Art: Material Matters (Sat) (Follow for all upcoming art events!)
🥾 Hike of the Week ( ): Kennedy Park (Lenox) Explore trail networks winding through acres of dense forests, with stunning views of the valley and local mountains covered in color.
• Ease: Family-friendly with trails of varying degrees of difficulty.
• Length: Wide, well-maintained paths from short walks to multi-hour treks.
• Sites: Stunning views of the Housatonic River Valley and Parsons Marsh. Look for hawks, owls, deer, and foxes!
🧗 Outdoor Adventures ( ): Our favorite adventure spots are open as the seasons change. Check the fall color from on high! Catamount (Catamonster zip line), Jiminy Peak (alpine slide/coaster), Ramblewild aerial park, and Berkshire East.
🏠 STAY: Looking for your group base in the Berkshires? Our 5-bed/5-bath home is ready for you. Save 15% mid-week for Fall with code WEEKDAY15. Link in bio to book direct! 🔗