Two Days in the Berkshires: Your Winter Wonderland Itinerary

Dreaming of a magical winter escape but unsure where to begin?

Spend 48 hours in the Berkshires to discover why the best kept secret of Western Massachusetts is the ultimate chilly-season getaway. Whether you’re planning a weekend retreat or a midweek adventure, solo or with a group, the Berkshires offers a unique and unforgettable experience, curated just for you! Picture cozy small-town charm, rich cultural experiences, breathtaking natural beauty, and just the right mix of relaxation and adventure. This jam-packed two-day itinerary is a perfect starting point – mix and match to tailor just for you. Ready to make some frosty memories? Let’s dive in!

Norman Rockwell Museum

Day 1

• Kick start your day with freshly baked treats and warm coffee at Marketplace Cafe in Pittsfield, then stop by Guido’s Fresh Marketplace for locally sourced car ride snacks!
• Travel to The Mount, Edith Wharton’s Home for a free, self-guided tour of the magnificent estate. (The main house is open spring through fall and there is an entry fee.) The grounds are gorgeous when blanketed in snow!
• Grab lunch (and a drink) at 110 Grill. Swing by Chocolate Springs on your way through for a sweet treat! 
• Check into your room at the Red Lion Inn. This iconic Berkshire location offers cozy charm around each corner. Say hi to the resident cats, Jack and Jane! 
•  Stroll Stockbridge Main Street and feel like you’ve stepped into a Norman Rockwell painting. After stopping at the shops, visit the Norman Rockwell Museum for tours through the galleries. Home to the world’s largest collection of Norman Rockwell’s iconic American illustrations, this museum is a must-see for art enthusiasts.
• Travel to Great Barrington to browse shops, for a delicious dinner at The Prairie Whale, then end the evening with live entertainment in the historic Mahaiwe Performing Arts Center. Robin’s Candy Shop offers nostalgic sweets for later!

The Barn Kitchen & Bar at the Williams Inn, credit Great Sky Media

Day 2

• Hit the road to head to North! Warm up with breakfast and a latte at Haven Cafe & Bakery in Lenox.
• On your travels, visit Lanesborough Local for some fun country store shopping and to stock up on provisions. Across the street you’ll find Inspired Creations for gifts.
• Ready to embrace the chilly weather charm? Hike at the Greylock Glen. The new Outdoor Center provides the perfect place to warm up by the fire with clear views of Mount Greylock. Or are you more of a snowshoe enthusiast? The Clark has trails ideal for snow exploration (they even have free snowshoes on-site) and admission is free through March!
• Head to Williamstown to check out the shops on Spring Street. Stop into The Barn Kitchen & Bar for a gourmet lunch, then tour the Williams College Museum of Art gallery or take in a film at Images Cinema.
• Check in for your stay at TOURISTS in North Adams, with amble views of the winter season from each room. Explore the expansive grounds and suspension bridge blanketed in snow. Then hop across the street to grab a tasty dinner and nightcap at the Trail House Kitchen & Bar.  

Photo by Christina Lane Photography

Are you looking for ways to unwind during your stay in the Berkshires? Check out one of our Cannabis Retailers or schedule a stop at one of our many Wellness offerings! Rather hit the slopes on your visit? The options are endless! Check out our Ski and tubing locations across the Berkshires, and explore more ways to get outdoors with Berkshires Outside. 

For more inspiration when visiting in winter, check out our Winter Brochure! Whether you’re marveling at world-class art, skiing through scenic trails, or indulging in farm-to-table cuisine, the Berkshires offers an unforgettable winter escape for every type of traveler. So pack your warmest layers and get ready to explore — adventure awaits #intheberkshires!

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