Fall in the Berkshires FAQs

Fall is the most magical time to visit the Berkshires! Between the crisp air and world-class leaf peeping, there is plenty to explore. For the most up to date info, check out our weekly blog page for things to do in the Berkshires:  This Weekend in the Berkshires

• Farm Fun & Festivals: For the classic autumn experience, visit Ioka Valley Farm (Hancock) or Whitney’s Farm Market (Cheshire) for corn mazes, pumpkin patches, hayrides, and legendary cider donuts. Taft Farms (Great Barrington) is another must-stop for pumpkins, a corn maze, and a beautiful fall foliage picnic area.
• Apple Picking & Orchards: Head to local favorites like Hilltop Orchards in Richmond for pick-your-own apples, orchard trails, and fresh cider donuts, or stop by Windy Hill Farms on Rt 7 between Stockbridge and Great Barrington for all the farm fall fun!
• Foliage Strolls & Estates: Visit Naumkeag in Stockbridge to walk the stunning Gilded Age gardens and see the famous Blue Steps framed by autumn colors.  In October your have to explore their legendary Pumpkin Show featuring thousands of glowing jack-o'-lanterns! Get tickets early through The Trustees.
• Fall Hikes: Hit the trails when the weather cools down! Explore the moderate trek up Dry Hill Reservation in New Marlborough, or take on Monument Mountain in Great Barrington for stunning panoramic valley vistas blanketed in fall colors.
• Spooky Season & Haunted Mansions: The Berkshires take on a wonderfully eerie vibe in the fall. Historic Gilded Age properties like Ventfort Hall in Lenox and The Mount host incredible ghost tours and candlelit autumn events. Check out our dedicated blog post on Berkshire Haunted Mansions & Fall Nights for all the spooky details!
• Theater & Culture: The cultural season extends right into autumn! Catch wonderful indoor performances and festivals at venues like Shakespeare & Company, Barrington Stage Company, and the Mahaiwe Performing Arts Center.
• Note: Some smaller sugarhouses or niche farms like Millbrook, High Hopes, or Shadowbrook are wonderful, but their availability often varies by the week—we recommend checking their social media pages directly before heading out!

Answer: You are minutes away from the county's top-tier venues! For an authentic barn vibe and great local energy, head to Buttonball Barn. If you prefer an industrial-chic setting with incredible acoustics, The Stationery Factory in Dalton is a must. For a more relaxed afternoon, Balderdash Cellars in Richmond offers live music paired with world-class vineyard views. For the intimate vibe, The Guthrie Center or the Lion’s Den. For an historic vibe: Saint James Place or Mahaiwe Performing Arts Center.

Check out all of our recommendations on our Berkshire Blog.

Answer: Our guests' favorite walkable breakfast is Starving Artist Creperie—be sure to try their toasted scone with butter! For a classic diner experience, Lee's Corner Kitchen is just a 10-minute stroll from the house. Our Berkshire Blog has many more recommendations for your stay.

Explore more insider favorites on the Berkshire Blog

Planning your visit? Berkshire House Stay is located close to it all. Staying with us means most everything is within 15 minutes, making your trip even more seamless. Click here to check availability: BHS Availability