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Weekend Connect: March 20-22

The Main Event: Stay Cozy & Summer Planning

The "Mud Season" 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 Three" are officially calling. If you are planning a summer visit, these dates belong on your calendar today:

  • Tanglewood: The 2026 schedule is officially live! 
  • Jacob’s Pillow: The 94th season features legends like the Paul Taylor Dance Company and the Pillow debut of the San Francisco Ballet. Sales start April 9.
  • Shakespeare & Company: Summer highlights include Twelfth Night in the outdoor amphitheater (July) and Hamlet in the Tina Packer Playhouse (August). Tickets and FLEXpasses are available now.


The Entertainment Shortlist 

This weekend offers a diverse range of theater and unique local experiences:

  • The Bulb Show: Visit the Berkshire Botanical Garden for a much-needed dose of color. It’s the perfect antidote to the lingering gray March weather.
  • Barrington Hall (Lenox): Catch the Picky Bastards on Saturday night (3/21) for a high-energy local performance. 🎸
  • Karaoke Night: For a bit of local fun, head over to the Dalton American Legion on Friday (3/20).

 ART

The Berkshires are world-renowned for their galleries, and this weekend is a great time to explore: 

  • The Clark (Williamstown): 🖼️ Take advantage of FREE admission thru end of March! It’s the perfect time to see their collection sans crowds.
  • The Wit Gallery (Lee): 🎨 Right on Main Street! Don’t miss their "Thought Provoking Art" exhibit—a must-see during your afternoon stroll through town.
  • Koussevitzky Gallery (Pittsfield): ✨ Explore the "Magical Beings" exhibit, running all weekend long

Local Fare and Seasonal Finds

Whether you’re looking for a stroll down Main Street or a quick drive to the surrounding towns, here is what’s on the menu this weekend:

  • The Heart of Lee (Walkable!): Stroll down the street from BHS to Starving Artist Creperie for their  toasted scone with butter—the ultimate local morning ritual.
  • A Short Drive Away: Head over to the Housatonic Farmer’s Market on Saturday morning (3/21) to stock up on local cheeses and fresh-baked breads to bring back to the BHS kitchen.
  • Last Tracks: It’s prime time for spring skiing! Grab the car and head to Butternut or Bousquet Mountain to catch the final runs of the season while the sun is out.

Live Music & Culture Calendar

From the barn to the vineyard, the county is humming:

  • The Egremont Barn: A quintessential Berkshire night out.  Hazzard County playing Saturday.
  • Balderdash Cellars: Spend Saturday afternoon sipping local wine and catching live tunes with the best views in the region. 🍷🎶


    FAQ's for the Season

    1. What are the best things to do in the Berkshires in March?

    • Answer: March is "Maple Season" and the start of spring blooms! We recommend visiting local sugar houses like Ioka Valley Farm, catching the Bulb Show at the Berkshire Botanical Garden, or taking advantage of Free March Admission at The Clark Art Institute.

    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 The Egremont 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 ski season...

    Cross-Country & Snowshoeing 

    For those who prefer a quiet glide through the woods over a downhill rush, Lee is the perfect base camp.

    • October Mountain State Forest (3 Mins): Literally in our backyard. It's the largest state forest in MA. While trails are not groomed, it is a local favorite for rugged "backcountry" cross-country skiing and snowshoeing.
    • Canterbury Farm (12 Mins): A dedicated Nordic center in Becket. They groom 22km of trails daily and offer rentals, lessons, and a cozy lodge with a fireplace.
    • Notchview (25 Mins): A high-altitude gem in Windsor. Because it's 2,000 feet up, they often have snow when the rest of the valley doesn't. They have over 3,000 acres of groomed trails.
    • Kennedy Park (10 Mins): Located right in Lenox. It offers beautiful, ungroomed carriage roads that are perfect for a casual morning ski followed by coffee in town.


    Bousquet Mountain (The "Local Legend")

    Best For: Families with kids, night skiing, and post-slope cocktails.

    • The Hub Logic: It’s so close (11 mins) that you can go for "twilight skiing" after a slow morning at the house and still be back in time for dinner by the fire.
    • The Vibe: Recently renovated with a great new lodge. It’s small enough that you won't lose the kids, but steep enough to keep adults happy.
    • Pro Tip: Their "Drifters" restaurant is genuinely good—try the local craft beer flight.


    Ski Butternut (The "Family Favorite")

    Best For: Long, scenic cruisers and a classic "New England" ski feel.

    • The Hub Logic: Located just 14 minutes south in Great Barrington. It’s the perfect "Saturday Mountain."
    • The Vibe: Known as the "Wapentake" of the Berkshires—very laid back, excellent grooming, and 100% snowmaking coverage. It feels like a hidden gem.
    • Pro Tip: If you have beginners in the group, their "Ski School" is widely considered one of the best in the Northeast.


    Jiminy Peak (The "Big Mountain" Experience)

    Best For: The serious skiers in your group and those who want a "Resort" feel.

    • The Hub Logic: A 22-minute drive through the beautiful North Berkshires brings you to the largest ski resort in Southern New England.
    • The Vibe: This is where you go for high-speed six-person lifts and a bustling "Village" at the base with shops and fire pits. It’s powered by 100% renewable wind energy!
    • Pro Tip: It can get busy on weekends. We recommend our guests head there early (8:30 AM) to get the "corduroy" snow before the crowds arrive.


    Catamount Mountain Resort (The "Border Crosser")

    Best For: Variety and thrill-seekers who want steeper terrain.

    • The Hub Logic: A scenic 25-minute drive from the house. It’s unique because the trails actually cross the state line between Massachusetts and New York.
    • The Vibe: It offers some of the most challenging terrain in the Berkshires (like the legendary "Catapult") but balances it with a cozy, updated base area and great fire pits.
    • Pro Tip: They offer excellent Night Skiing on 15 trails—perfect if your group wants to spend the morning at a museum and hit the slopes after 4:00 PM.




    Berkshire East (The "Eco-Adventure")

    Best For: Serious skiers and sustainability fans.

    • The Hub Logic: About 45 minutes north, but worth the drive for a full-day excursion.
    • The Vibe: It is the first ski area in the world to be 100% powered by onsite renewable energy (wind and solar). It has a "big mountain" feel with long, rugged trails.
    • Pro Tip: Check out their $25 Wednesday Night Skiing deal if your guests are staying mid-week—it’s the best value in the state.
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