This Weekend in the Berkshires 10/16-10/18
October in the Berkshires: Fall Foliage, Pumpkins & Harvest Fun
What a beautiful time of the year. We are right in peak leaf peeping with plenty happening around the Berkshires. Be sure to check out the big spots celebrating the season like Naumkeag, The Mount, Hancock Shaker Village, and Ventfort Hall, alongside local farms across the county—including Highlawn, Windy Hills, Taft, Second Drop, and Hilltop—always providing the best of the season.
Whether you are staying with us or just need a good itinerary, check below for events, music, art, food, shopping, and hiking this weekend! Grab your group, plan your getaway, and come experience peak fall magic with us. Click here to book direct and save
✨Events & 🎭 Theater: (This isn't everything, but it’s a lot of it!!)
- 10/16: The Mount Ghost Tour — Chilling evening tours through Edith Wharton’s haunted historic estate.
- 10/16: The Barn @ Lee: Real Estate — A compelling live theatrical performance presented in Lee.
- 10/16–10/18: WAM / Shakespeare & Company: Camp Siegfried — A gripping, thought-provoking drama staged in the Bernstein Theatre.
- 10/1–10/31: Naumkeag Pumpkin Show — Thousands of glowing jack-o'-lanterns transforming Stockbridge's historic estate. Be sure to get your tickets online in advance!
- 10/17: All Hallows Lee — Downtown festival celebrating autumn community spirit and seasonal fun.
- 10/17: Hancock Shaker Village Pumpkin Extravaganza — Glowing carved pumpkins and family-friendly festivities around the historic round barn.
- 10/17: Books & Cake (Hillsdale, NY) — A special event featuring a wonderful pairing of live music and curated books, plus coffee and cake just across the border.
🎸 Live Music
Always good music vibes in the Berkshires! Catch these live sets across the county all weekend long:
Anthony Geraci at Stationary Factory (Friday)
- Kollin Kozlowski at Antimony Brewing (Friday)
- Vitamin String Quartet at The Mahaiwe (Friday)
- Meg Gehman at Away Lodge (Saturday)
- James Taylor Reimagined at Buttonball Barn (Saturday)
- Frank Lind at Berk Mntn Distillers (Saturday)
- Michael Junkins & Friends at Lion’s Den (Sunday)
🎨Art & Gallery Exhibits:
There is always a brilliant gallery to explore across the county—some indoors, some framed by crisp autumn air:
Devries Fine Art(Middlefield): The Sculpture Trail— A fun outdoor adventure combining art, poetry, and nature walks (All Weekend - weather permitting!).
Ozzie’s Glass Gallery(South Lee): Hand-crafted glass: Fun, and maybe you can catch Ozzie at work in the studio.( All Weekend)
Art on Main (West Stockbridge): "Chasing Shadows" exhibition (All Weekend).
Art in Berkshires Gallery: "As I See It" Artist Talk (Saturday).
The Wit (Lenox): “Hannah” by John Petrey (All Weekend).
Becket Art Center (Becket): Sculptural Installation (All Weekend).
Follow @artintheberkshires for all upcoming art events!
🛍️Shopping - Books:
We rotate our shopping towns weekly. When you are doing the WAM, Camp Siegfried Weekend, here are the cool shops in Lenox to check out:
Lykke Living: Danish happiness for you and friends.
The Bookstore & Get Lit Wine Bar: A grown-up afternoon; enjoy a conversation with the owner.
Concepts of Art: Gifts from all across the world.
Wilcox & Co: Unique selection for gifts or to take home.
Catwalk Boutique: Where shopping saves animals.
Glad Rags: Spice it up a bit with this lovely team.
Shooz: Sometimes shoes, sometimes hats, always cute!
Dare Bottleshop: Most weekends, they have afternoon wine tastings.
🍴 Good Food & Dining
Working up an appetite exploring the foliage? Here are our top dining selections across the towns this week:
Lee (Walkable from BHS):
- The Mint: Sunday Brunch
- Roses: Get the biscuits!
- Lee’s Corner Kitchen: Breakfast/lunch, great owners
Becket:
Neon Newt: Weekend Brunch, Fancy dinner Mondays!
Lenox:
Olde Heritage: Local hangout for burgers and beers
Brava: Tapas, Pizzas, Craft Cocktails
Great Barrington:
GB Eats: Exceptional service, excellent breakfast and lunch
The Well: Good food, good drink, good company!
(Craving dessert? Order a custom cake from @shellycakes413 for home!)
🥾Hike of the Week: Steven's Glen
Explore a stunning waterfall cascading through a romantic rock cleft, a deep and quiet hemlock forest, and a tranquil reflection platform built for quiet reflection.
- 🥾 Ease: Moderate 1.2-mile round-trip trail that offers an engaging walk through varied terrain.
- 🗺️ Length: About 1 hour of total hiking time to complete the loop and enjoy the sights.
- ✨ Sites: A cascading waterfall through a romantic rock cleft, deep hemlock groves, and a viewing platform with a reflection bench.
- 📍 Location: Straddling Richmond and West Stockbridge, MA.
🧗 More Outdoor Adventures
Only a few more weeks left for our summer playgrounds (start thinking SKI!):
- Catamount: Hit the "Catamonster" zip line and one of the largest aerial adventure parks in the country (we had a blast here last week!).
- Jiminy Peak: Ride the legendary alpine coaster, mountain coaster, and scenic chairlift rides.
- Ramblewild: Explore a massive tree-to-tree aerial park hidden deep in the forest canopy.
- Berkshire East: Ride the Thunderbolt Mountain Coaster or hit the world-class bike park.
🎟️ Berkshires Travel Tip: Fall Foliage: Follow us on Instagram. We have several fall foliage day trips around the area!
Planning your visit? Berkshire House Stay is located close to it all. Staying with us means everything is within 15 minutes, making your trip even more seamless. Click here to check availability: BHS Availability