What you'll do
Savor the flavors of fall in the Berkshires with a culinary-focused weekend that highlights the region’s best farm-to-table dining, wineries, cider houses, and local markets. Start your trip with brunch at beloved cafés like Haven Café & Bakeryor Six Depot Roastery, then spend your afternoons wine tasting at Balderdash Cellars, sampling cider at Hilltop Orchards, or enjoying craft cocktails and small-batch spirits at Berkshire Mountain Distillers. Evenings are reserved for memorable meals at acclaimed restaurants such as Prairie Whale, Cantina 229, and Alta Restaurant & Wine Bar, where menus showcase fresh, seasonal ingredients. Along the way, stop at farm stands and pumpkin patches for true autumn flavors, from cider donuts to harvest produce. With cozy stays at the Apple Tree Inn in Lenox or the historic Red Lion Inn in Stockbridge, this itinerary blends world-class dining with rustic New England charm — the perfect way to experience the Berkshires in fall.
Day 1
Recommended Hotels
Apple Tree Inn or Red Lion Inn
Apple Tree Inn
酒店
Charming retreat in Massachusetts
Perched on a hillside in Lenox, the Apple Tree Inn combines historic charm with modern style. Guests can relax in well-appointed rooms, enjoy live music in the Ostrich Room bar, or savor seasonal dining overlooking the mountains. A favorite for fall foliage getaways and cultural trips to Tanglewood.
To book this property with exclusive perks, message me or email ryan.jones@fora.travel.
Arrival & Lenox Flavor
Morning:
Arrive in Lenox and ease into the trip with brunch at Haven Café & Bakery for fresh pastries and cozy brunch plates, or head to Six Depot Roastery & Café in West Stockbridge, where coffee roasting meets art gallery vibes.
Haven
咖啡店
Charming getaway in Massachusetts
Haven is a cozy little spot in Massachusetts, nestled at the coordinates 42.3596° N latitude and -73.2833° W longitude. It’s one of those places that feels like a hidden gem, perfect for anyone looking to escape the hustle and bustle. The vibe is laid-back, making it a great place to unwind and enjoy some downtime. Whether it's the scenic views or the friendly locals, Haven has a charm that draws people in and keeps them coming back for more.
Afternoon:
Spend a couple of hours exploring Lenox’s charming downtown shops and galleries. For an afternoon tasting, head to Hilltop Orchards & Furnace Brook Winery for cider and wine sampling, plus a stroll through the orchard if time allows.
Hilltop Orchards Winery, Cidery and Taproom
winery
Charming winery and cidery
Hilltop Orchards, located in Massachusetts, is a charming spot that combines the best of nature and local craftsmanship. It’s home to Furnace Brook Winery and Jmash Cidery, where visitors can enjoy a variety of wines and ciders made from fresh, locally sourced ingredients. The atmosphere is relaxed and inviting, making it a perfect place for friends and family to gather. The Taproom at Hilltop Orchards offers a cozy space to sample these delicious beverages while soaking in the beautiful orchard views. Whether you’re a wine enthusiast or just looking for a fun outing, this place has something for everyone.
Evening:
Dinner at Alta Restaurant & Wine Bar, where Mediterranean-inspired dishes pair beautifully with an extensive wine list. Overnight at Apple Tree Inn for boutique charm and live music in the Ostrich Room, or at the Red Lion Inn in Stockbridge for historic New England ambiance.
Alta
餐厅
Charming small community in Massachusetts
Alta is a small community located in Massachusetts, nestled at a latitude of 42.3573 and a longitude of -73.2829. It’s one of those charming spots that might not be on everyone’s radar but has its own unique vibe. The area is characterized by its scenic surroundings and a laid-back atmosphere, making it a nice place for those who appreciate a quieter lifestyle. Residents enjoy the natural beauty of the region, with plenty of opportunities for outdoor activities like hiking and exploring local parks. Alta has a friendly feel, where neighbors know each other and there’s a sense of community that makes it special.