A three-day getaway to the Berkshires offers outdoor adventure, cultural experiences, and world-class dining. Surrounded by gorgeous scenery, this charming four-season destination in western Massachusetts has something for everyone. We’ve curated an itinerary to help you plan the ultimate Berkshires weekend escape, featuring scenic hikes, fine dining, and a little boutique shopping.
Book a favorite room at our romantic bed and breakfast near Lenox, MA. A central location that allows easy access to great activities and adventures. Then relax and unwind with an onsite program of enriching activities and events on the property.
Let’s explore what makes a perfect 3-day getaway to the Berkshires.
Day 1: Road Trip to the Berkshires
Reaching our elegant country retreat becomes part of the adventure. Those driving from Boston or New York City can enjoy scenic routes through small New England towns. Once you arrive, a trip to the Berkshire Botanical Garden makes for the perfect introduction. Stroll through 24 acres of beautifully landscaped grounds setting the tone for a weekend escape.
Lunch Stop: Before checking in, visit Once Upon a Table, located on Main Street in Stockbridge, this cozy eatery provides an excellent introduction to the Berkshires dining scene.
Guest check-in begins at 3:00 PM. Kick off your shoes and settle into a romantic accommodation. Suites and private cottages offer spa tubs to ease travel fatigue. When weather permits, a dip in the heated pool provides refreshment. Strolling along Meadow and Wilderness Trails across our 32-acre private property provides a relaxing intro to the weekend. Sitting in an Adirondack chair on the expansive lawn and admiring the view creates a moment of pure tranquility.
Dinner & Drinks at The Barrington Brewery
A casual yet satisfying dinner awaits at The Barrington Brewery in nearby Great Barrington. This charming spot serves hand-crafted beer and from-scratch pub fare six days a week. The menu features an array of soups, salads, sandwiches, barbecue, and comfort food. A signature ale or seasonal tap brew completes the experience.
Evening Wind Down
After dinner, return to the Inn and settle into the library, cozy sitting room, or seasonal sunroom. The firepit outside offers a warm gathering space for guests to enjoy good company. A luxurious guest room promises restful sleep at the end of the first day.
Day 2: Explore the Berkshires
Breakfast of Champions
Wake up to the smell of freshly brewed coffee. A breakfast spread of fresh fruit, yogurt, granola, and home-baked goods that fills the sunlit dining room. And enjoy the sweet or savory entrée of the day.
Morning Hike to a Waterfall
Begin the day with a hike in the woods to a beautiful waterfall. Bash Bish Falls showcases twin falls cascading down a granite rockface into a deep pool. Those preferring a gentler hike can explore a scenic loop around a lake or pond. Another option includes visiting Stephen’s Glen in West Stockbridge, which features a stunning waterfall surrounded by lush forest.
Leisurely Lunch in Town
Hiking takes a lot of energy, so a leisurely lunch is the best way to replenish it. Check out Alta in Lenox for delicious Mediterranean-inspired eats. Experience exceptional service and an impressive wine list before heading out for an afternoon at a local museum.
Visit to the Norman Rockwell Museum
Norman Rockwell, the iconic American illustrator featured on 323 covers of the Saturday Evening Post, lived and worked in Stockbridge, MA for much of his career. His museum is a living showcase for his downhome illustrations of American society. The much-loved museum features a revolving series of exhibitions, permanent collections, and archives.
A Fine Dining Adventure
For an unforgettable fine dining experience, Café Triskele (formerly Chez Nous) takes pride in serving the finest and freshest ingredients available. This European-style bistro and brasserie is a welcome addition to the food scene on your Berkshires getaway. Book a table for two and dive into an eclectic selection of entrees and appetizers with a distinctive French flair.
Day 3: A Relaxing Send-Off
After a cozy night’s sleep and recharging your batteries from the previous day, visit the breakfast room and decide on Chef Jim’s divine Eggs Florentine or something sweet like maple-glazed French toast. If you’re feeling adventurous, try the honey-pecan waffles. Whichever you choose, it’s sure to satisfy. Continue the slow morning by lingering over a cup of coffee and admiring the stunning view outside before returning to your room to pack.
Treat yourself to a little retail therapy before heading home. Visit the charming shops and boutiques that line the main streets of Lenox and Stockbridge. If you love outlet shopping, stop by Lee Premium Outlets for designer deals. Discover a treasured antique to bring home with you, then stop by High Lawn Farm for the perfect sweet treat before heading out of town.
Plan Your Next Visit
Memories of the perfect 3-day getaway in the Berkshires will linger long after returning home. As the seasons change, so does the scenery! And as we creep into spring, the waterfalls begin to overflow, the trees fill out once again, and the scent of fresh flowers fills the air. A new season means there’s so much more to see. Plan your next visit and let Devonfield Inn welcome you back for another unforgettable escape.
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