What you'll do
Escape to the Berkshires this fall for a romantic foliage getaway filled with cozy inns, scenic drives, and unforgettable dining. Base yourself in Stockbridge or Lenox with a stay at the luxurious Blantyre or the historic Red Lion Inn, both offering classic New England charm. Drive the winding Jacob’s Ladder Scenic Byway, one of the most beautiful fall foliage routes in Massachusetts, before enjoying an intimate wine tasting at Les Trois Emme Winery. In the evening, savor a candlelit dinner at the Old Inn on the Green, where flickering light and seasonal cuisine set the mood. Add a sunrise hike at Laura’s Tower or Olivia’s Overlook for breathtaking views, and spend time strolling through the charming towns of Stockbridge and Lenox, with their boutique shops, historic streets, and small-town romance. This itinerary blends autumn scenery, fine dining, and timeless New England ambiance for the perfect couples’ getaway.
Day 1
Arrival & Scenic Drive
Late Afternoon:
Arrive in the Berkshires and check in to your romantic base — choose between The Prospect Berkshires, a lakeside mountain retreat with modern cabins, or Berkshires Untold, a retro-inspired boutique hotel in Lenox with stylish, creative flair.
Prospect Berkshires
hotel
Charming outdoor getaway in Berkshires
Set on a serene mountain lake at the crossroads of Massachusetts, New York, and Connecticut, The Prospect Berkshires blends modern design with nature. Its 49 year-round cabins are inspired by the Transcendentalists, designed for gathering, unwinding, and reconnecting with the outdoors. Amenities include a pool, sauna, tennis, and lakeside dining, with sunsets that feel timeless.
To book this property with VIP perks, message me or email ryan.jones@fora.travel.
Optional Activities
If time allows take a short drive over to the historic town of Stock Bridge. Check out the shops and the historic Red Lion Inn. If time allows grab a drink at the bar and relax on the iconic porch.
or
Head on over to Balderdash Cellars for a wine tasting and fall views out over the lake.
Stockbridge
area
Charming historic town in Massachusetts
Stockbridge is a charming little town nestled in the Berkshires of Massachusetts. Known for its picturesque landscapes and rich history, it offers a delightful mix of art, culture, and outdoor activities. The town is famous for its connection to the artist Norman Rockwell, whose former studio is now a museum showcasing his iconic works. Visitors can stroll through the quaint streets lined with unique shops, cozy cafes, and beautiful historic buildings. Nature lovers will appreciate the nearby hiking trails and scenic views, especially around the Stockbridge Bowl, a lovely lake perfect for swimming and picnicking. With its friendly vibe and stunning surroundings, Stockbridge feels like a slice of New England charm.
Bar & Restaurant at The Red Lion Inn
bar
Cocktail bar & restaurant
Surrounded by crystal chandeliers, antique china and colonial pewter, our historic Main Dining Room is an ideal place to spend a romantic evening or mark a special occasion. Long the focal point of our culinary reputation, the dining room’s menu features a blend of traditional favorites and contemporary interpretations of classic New England fare. Our wine list, featuring over 300 selections, is a perennial recipient of Wine Spectator’s Award of Excellence.
Balderdash Cellars
winery
Charming Massachusetts winery
Balderdash Cellars is a charming winery located in Massachusetts, nestled at latitude 42.4160108 and longitude -73.3360973. Known for its laid-back vibe, this spot offers a delightful selection of wines that reflect the local terroir. Visitors often rave about the friendly atmosphere and the knowledgeable staff who are always ready to share their passion for winemaking. The picturesque setting makes it a perfect place for a casual outing with friends or a romantic afternoon. Whether you're a wine enthusiast or just looking to enjoy some good company, Balderdash Cellars has something for everyone.
Evening:
Ready for dinner? — try Cliff House on sight at Prospect - or if you're staying at Berkshire Untold try their on sight dinning at The Club Room.
The Cliff House
restaurante
Charming dining spot with views
The Cliff House is a charming spot located in Massachusetts, nestled at the coordinates 42.1949499 latitude and -73.4464822 longitude. It’s known for its stunning views and inviting atmosphere, making it a popular destination for both locals and visitors. The place has a laid-back vibe, perfect for enjoying a meal or just soaking in the scenery. With its unique blend of natural beauty and cozy ambiance, The Cliff House offers a delightful escape from the everyday hustle and bustle. Whether you're grabbing a bite to eat or simply taking in the sights, it's a great place to unwind and enjoy some quality time.