Weekend Connect: May 1 - May 3
Start your Summer Planning
May in the Berkshires is often our best-kept secret. While the hills are quiet, the cultural calendar is bursting with energy. This weekend, we have your list of must-see events.
The Summer Giants: Secure Your Spot Now The "Big Four" are officially calling. If you are planning a summer visit, now is the time to secure your dates:
- Tanglewood: The 2026 schedule is officially live!
- Jacob’s Pillow: The 94th season tickets are now on sale.
- Shakespeare & Company: Summer highlights include Twelfth Night. Tickets are available now.
- Edith Wharton - The Mount: The 94th season tickets are now on sale.
Spring Special: Stay for the story. We are offering a 3rd Night Free for direct bookings through May 18th! Use code SPRING2026 at checkout.
Events
Always something to see in the Berkshires:
- Baby Animals at the Village: A spring tradition! Head to Hancock Shaker Village all weekend to meet the newest additions to the farm. 🐏
- Dance at the Pillow: Don't miss inDance, Rowdies in Love at Jacob’s Pillow in Becket- merging Bharatanatyam with contemporary dance. 💃
ART
The Berkshires are world-renowned for their galleries, and this weekend is a great time to explore:
- The Wit Gallery (Lenox): Don't miss their new artist, pricilla robinson during your afternoon stroll through town. 🎨
- Ozzie's Glass Gallery: Head to south Lee and watch Ozzie create these lovely works of Art.
Local Fare and Seasonal Finds
Stroll down Main Street for Lee Restaurant Week:
- Cafe Triskele: Our #1 BHS Top Pick. Chef-driven, cozy, and inventive.
- The Station: Refined dining in the historic Gastropub setting.
- Mint: Waterfront Indian cuisine that is a must-try for families.
- Agave’s: Incredible Mexican flavors and the best service in town.
- 51 Park: Your go-to for classic American favorites on Main St.
Live Music & Culture Calendar:
- Balderdash Cellars: Jason & Trev take the stage this Saturday. Pair the music with their great wine and the local food truck on-site. 🍷
- Buttonball Barn: For a nostalgic night of sound, don't miss Neon Avenue (Saturday) in this unique, intimate venue. 🎸
FAQ's for the Season
1. What are the best things to do in the Berkshires in Spring?
- Answer: We like to head to Naumkeag for the Flower Festival, Hancock for the baby animals, find the latest at the Berkshire Botanical Garden, or getting your hike on with the many lovely trails in the area.
2. Where can I find live music and entertainment in The Berkshires?
- Answer: You are minutes away from the county's top-tier venues! For an authentic barn vibe and great local energy, head to Buttonball Barn. If you prefer an industrial-chic setting with incredible acoustics, The Stationery Factory in Dalton is a must. For a more relaxed afternoon, Balderdash Cellars in Richmond offers live music paired with world-class vineyard views.
3. What is the best "Insider" breakfast spot in Lee?
- Answer: Our guests' favorite walkable breakfast is Starving Artist Creperie—be sure to try their toasted scone with butter! For a classic diner experience, Lee's Corner Kitchen is just a 10-minute stroll from the house.
And since it is Spring:
Naumkeag: The grounds are open and ready for a quiet spring stroll. It’s the perfect time to explore the famous Blue Steps and the 48-acre Gilded Age estate. The architecture and mountain views are stunning year-round, but there is a special magic to the gardens as they begin to wake up.
Naumkeag's Daffodil & Tulip Festival Mark your calendars for 4/18-5/10!
- The Blooms: Over 100,000 daffodils and tulips will carpet the gardens in a massive display of color.
- The Experience: Explore the vibrant container displays, seasonal decorations, and self-guided tours of the historic house's first floor.
- Insider Tip: This is a timed-entry event and it always sells out. If you’re planning to be in town after the 18th, grab your tickets now at thetrustees.org.
No Mud (or Little) Hikes
The best spring views don't always require hiking boots. Here are four local favorites, ensuring you get all the fresh mountain air without the messy cleanup.
- The Mount, Lenox -7 minutes from BHS. Edith Wharton’s gardens and forest trails are free and open to the public year-round (dawn to dusk). The main paths are well-maintained crushed gravel, making it a sophisticated, dry way to see the first spring bulbs.
- Tanglewood Grounds, Lenox -7 minutes from BHS
Before the summer concert season begins, Tanglewood’s 200+ acres are a quiet secret. Stick to the paved service roads and hard-packed walkways to enjoy the famous "Shed" views and the Stockbridge Bowl overlook without the "Mud Season" mess. - Ashuwillticook Rail Trail, Lanesborough -15 minutes from BHS. This 14-mile former railroad track is fully paved and follows the edge of the Cheshire Reservoir. It’s the gold standard for spring because you get wide-open water views and mountain vistas without a single patch of mud.
Baby Animals
The best spring views don't always require hiking boots. Here are four local favorites, ensuring you get all the fresh mountain air without the messy cleanup.
- Hancock Shaker Village, Hancock -18 minutes from BHS
This is the big one. Starting mid-April 2026, the Round Stone Barn is filled with newborn lambs, piglets, calves, and chicks. It is hands-on and incredibly heartwarming. - High Lawn Farm, Lee -2 minutes from BHS
You can often see the young Jersey cows in the fields or near the barns on your driving adventures. Their big, soulful eyes are the unofficial mascot of Lee! Stop and pet the young-ins.
- Ioka Farms, Hancock -25 minutes from BHS
Head to the barnyard to see the specialty farm animals. It’s a great spot for kids to learn about the "sugaring" woods and the animals that live there.
Holiday Brook Farm, Dalton -20 minutes from BHS
A true working farm where you can see the cycle of farm life up close. Check their schedule for weekend visits where you can say hello to the calves and grab a fresh farm snack.