09/05/2026
www.berkshirehousestay.com
Planning a scenic escape this fall? 🍁🚗 As we kick off our new series of classic Berkshire day trips, we’re starting right from our front door in Lee. Buckle up for this lovely autumn drive heading west into the historic towns and rolling hills toward the NY border.
Drop these exact stops into your Google Maps and you're ready to roll:
• Starving Artist or Lee's Corner Kitchen, Lee, MA
• Stockbridge Coffee and Tea, Stockbridge, MA
• First Congregational Church, Great Barrington, MA
• Hillsdale General Store, Hillsdale, NY
• Olde 1811 Antique Shoppe, Chatham, NY
• Balderdash Cellars, Richmond, MA
• Berkshire House Stay, Lee, MA
Lee ☕ Meet in Lee: Every great road trip needs a starting line, and beautiful Lee is the place to be. Meet up with your crew for a relaxed morning bite—whether that’s a sweet pastry at Starving Artist or a classic, hearty breakfast at Lee's Corner Kitchen—before we hit the scenic back roads.
Stop 1: Stockbridge Stroll & Shop 🍂 Historic Stockbridge: Park at Stockbridge Coffee & Tea to kick off your stop! Browse gifts at Side Tracks, walk over to the iconic Red Lion Inn to check out Shop Around the Corner, and stroll back up Main Street to pop into Whispered in the Heart, BerkCHEERS, and NeJaime’s—then loop back for a treat at the coffee shop. ✨ Not a shopper? Stroll west down Main Street to take in the historic homes, or walk over to Naumkeag to explore the stunning autumn gardens if you've got the energy!
Stop 2: Great Barrington 🚗 The Drive: Cruising south on Route 7 toward Great Barrington, keep your eyes peeled as Monument Mountain rises up right alongside the road, framed by incredible bursts of autumn color. 🍎 Harvest Stops & Great Barrington Stroll: Right on Route 7 as you head out of Stockbridge, make a quick stop at Windy Hill Farm to pick your own autumn apples or select a pumpkin for the season. Park near the First Congregational Church and head out on foot! Browse the unique finds at Fripperie and explore the charming local shops lining Main Street. Afterward, take a peaceful meander along the Riverfront Trail to watch the fall foliage drape over the Housatonic River. 🍔 Lunch Stop: Hop back in the car for a quick drive to Bistro Box (open through October!) to grab a fantastic outdoor lunch in the crisp autumn air before heading further west.
Stop 3: Hillsdale, NY 🚗 The Drive: The journey over to Hillsdale treats you to sweeping, open-air views of the valley as you wind through the Taconic Range and get closer to the New York border. 🛍️ Crossing into New York: Park in front of the Hillsdale General Store and spend a happy hour exploring—don’t forget to check out the antiques upstairs! Step right across the street to HG Kitchen for wonderful cookware and gadgets, and visit Books and Cake on the other side for a wonderfully curated read (and, of course, a sweet slice of cake). 🍎 C***r Stop: If you have time before heading out, make a quick detour over to Little Apple C***ry for a lovely afternoon tasting.
Stop 4: Chatham, NY 🚗 The Drive: Winding your way north from Hillsdale toward Chatham on classic two-lane roads, you glide right through the scenic Harlem Valley and its historic farm hamlets, surrounded by rolling hills draped in vibrant fall foliage. 👻 Historic Wandering in Chatham: Begin your Chatham stop at the Olde 1811 Antique Shoppe—housed in Chatham’s oldest building, it’s an absolute blast to explore (and especially atmospheric around Halloween!). Afterward, wander down Main Street to check out the unique local boutiques and treat your crew to something sweet at Fork and Whisk Bakery.
Stop 5: Balderdash Cellars 🚗 The Drive: Winding your way east from Chatham over toward Balderdash Cellars in Richmond takes you across some of the prettiest country roads in the region—drifting past quiet rural farmlands, over gentle ridges, and down into the peaceful valleys just west of the Berkshires' interior. 🍷 Final stop in Richmond: Make your way over to Balderdash Cellars in Richmond—one of our absolute favorites! Drop in to enjoy some fantastic w**e, live music and food trucks on most weekends, and the warmest hospitality from owners Donna, Christian, and their wonderful staff. It’s the ultimate spot to unwind together in the afternoon.
Berkshire House Stay 🏠 Your Home Base in the Berkshires: Why rush home when you can make a full weekend out of it? Located right in the center of Lee, Berkshire House Stay is the ultimate cozy headquarters for your group getaway. With plenty of space featuring 5 bedrooms and 5 baths, a fantastic private backyard, and a wonderful porch for morning coffee or evening unwinding, there is plenty of room for everyone to spread out and relax together. ✨ Ready to gather your crew? Share this post with your travel partners, plan your autumn escape, and come stay with us! Skip the platform fees and save 15% mid-week for Fall using code WEEKDAY15. Link in bio to book your stay directly with us!
