Life Style

What To Do & Where To Eat in Winter 2024

If you’re looking for a seamless winter escape from the hustle and bustle of daily life, consider yourself in luck. I recently had the chance to steal away for a winter adventure weekend in the Berkshires, courtesy of Explore Western Mass, and am here with the ultimate fun-filled itinerary to suit just about everyone’s travel needs. Unless you live in a climate that’s warm year-round, staying active in the winter is all about getting into the snow—and of course, a little bit of après ski action paired with delicious bites and tasty sips. The Berkshires offers that—and so much more...READ THE FULL STORY HERE▶

Keep reading to learn the best ways to have the perfect active winter getaway in the Berkshires, plus, what to eat and where to stay.

Winter activities in the Berkshires:

Contrary to what you may believe, the Berkshires are brimming with winter activities that go far beyond skiing and snowboarding. Don’t get me wrong, it’s certainly a haven for those who love to hit the slopes, but there are many other fun mountain activities, intimate eateries, and downtown shops and boutiques you can enjoy as well.

1. A beer tasting at White Lion Brewing

White Lion Brewing
Alexa Mellardo

What’s a winter weekend getaway without a few good brews? You’ll miss out if you don’t stop at White Lion Brewing Company. I enjoyed a beer tasting and tour of White Lion’s Springfield location on my way to the Berkshires, complete with fried catfish bites, sesame ribs, mixed greens salad, and Brussels sprouts with actual honeycombs. As far as beers go, my favorite was the Blueberry & Marshmallow—such a unique treat!

White Lion’s founder, Raymond Berry, and his team do everything to make this experience top-notch. Kick back, enjoy, and tell Raymond I sent you!

2. Snow tubing at Bousquet Mountain

snow tubing
Alexa Mellardo

History buffs will enjoy learning that before becoming a ski mountain, the land was a mink farm owned by Clarence J. “Clare” Bousquet. Bousquet Mountain is the oldest ski area in the Berkshires and is known for bringing night skiing to life.

I kicked off my first night in the Berkshires snow tubing at Bousquet—because snow tubing isn’t just for kids! The charming base of Bousquet offers fire pits where you can snuggle up and take in the picturesque sunset melting into the slopes. It’s so easy to make the moment your own with a night of snow tubing with family, friends, or your significant other. The mountain offers four large tubing lanes that provide plenty of room to make core memories. It felt invigorating as I flew down the mountain in my tube and made my way back up the carpet lift for some more runs.

3. Snowshoeing at Jiminy Peak

snowshoeing and skiing
Alexa Mellardo

According to research, snowshoeing is considered one of the “top 20 participatory sports in the United States”—and for good reason. If you’ve never tried snowshoeing before, I strongly urge you to buckle up some snowshoes and hit the trails.

This winter sport was an incredibly peaceful way to clear my mind. I took in the snowy sights along Jiminy Peak’s John Hancock trail while going at my own pace uphill; it was an incredible cardio workout. (My legs and glutes felt the burn after my snowshoe session, in the best possible way!) Snowshoeing is also an excellent calorie burner. Science says this activity expends a comparable amount of energy to walking, but you can snowshoe at a slower pace to achieve the same effects.

4. Riding the Mountain Coaster at Jiminy Peak

mountain coaster
Alexa Mellardo

If you’re game for a different kind of ride up and down the mountain, consider swapping out your skis and hopping aboard Jiminy Peak’s Alpine Coaster, where you can take in the landscape at up to 23 mph. In my opinion, this is one of the coolest attractions offered at a mountain resort to take a short break from the ski day. (And it’s family-friendly!)

The ride up the mountain is slow and steady, and you control how fast your cart goes down the mountain by adjusting the speed handles. It was such an invigorating ride winding through the snow-covered trees with the cool breeze rushing through my hair. The winter views are truly breathtaking, and I can only imagine how jaw-dropping it looks in the fall.

5. Skiing at Berkshire East

Berkshire East skiing
Alexa Mellardo

One full day in the Berkshires was all about skiing the slopes at Berkshire East. This mountain resort gave such a cozy, local, welcoming vibe from the lodge to the base to the complimentary s’mores at the LLBean S’mores Shack after a long day in the snow. It’s a perfect mountain for beginners and advanced skiers/snowboarders alike to feel right at home, with the full gamut of beginner trails to double black diamonds. I only skied here, but the mountain also offers snow tubing and alpine racing.

Where to stay:

Hotel on North

Hotel on North
Alexa Mellardo

Hotel on North is a quaint boutique hotel situated in the heart of downtown Pittsfield, MA. It’s a convenient 10-minute drive to Bousquet Mountain and a short walk to tasty eateries and cafés. You may even be lucky like me and meet an artist showcasing their latest collection or something just as cool in the hotel lobby!

What I enjoyed most about Hotel on North is the love and character that fills every inviting nook and cranny, from the vintage suitcases to the leather and velvet furniture to work from local artists decorating the walls. It’s easy to simply curl up with a book and kick back. Not to mention, the hotel understandably boasts that every guest room is unique. Mine was complete with a comfy king-size bed, two plush velvet chairs, a vintage radio, a kitchen, and of course, artwork covering the walls.

I’m told Pittsfield has more of an urban vibe compared to the more quaint surrounding towns; if you’re looking for a traditional New England vibe, there are also plenty of charming inns, hotels, and B&Bs in surrounding towns like Great Barrington and Lenox.

The Williams Inn

Williams Inn
Alexa Mellardo

For an upscale, modern farmhouse aesthetic, consider The Williams Inn, a property I absolutely fell in love with. The central fireplace is an ideal gathering area for playing a game of chess or enjoying a glass of wine. I loved exploring the entire hotel, although my oh-so-comfortable room made it quite challenging to head downstairs for dinner. I had the most amazing view of downtown Williamstown, MA with the mountains and sunset setting the perfect backdrop. The shiplap-adorned walls, rocking chairs on the front porch, and barn door accents provide an overall home-away-from-home feel. The best part? The Williams Inn is a short 20-minute drive to Jiminy Peak and a 40-minute drive to Berkshire East.

Where to eat:

Dottie’s Coffee Lounge

Dottie's Coffee Lounge
Alexa Mellardo

Fueling up for a day on the mountains is essential, and it’s nice to have that one breakfast/lunch spot you can always count on. Dottie’s Coffee Lounge is that go-to place you’ll be looking for, and it’s walking distance from Hotel on North. The best thing about Dottie’s is they really know how to jazz up a classic egg breakfast sandwich. The Berkshire Breakfast Sandwich is to die for, and includes scrambled eggs, cheddar cheese, mixed greens, red onion, and homemade caper pesto on fresh sourdough bread (I added tempeh bacon to mine!).

Methuselah Bar and Lounge

Methuselah Bar & Lounge
Alexa Mellardo

You may have heard of Methuselah, the 969-year-old biblical man, or perhaps, Methuselah, the 14.5-billion-year-old star, which is older than the entire universe. But you may not have heard of Methuselah Bar and Lounge in the Berkshires, which is right down the street from Hotel on North. In my book, it’s a legend in itself.

Created by owner Yuki Cohen, this trendy eatery offers everything from whimsical cocktails to organic, locally grown menu items. I savored a cheese and charcuterie board and sesame shoyu roasted portobello mushroom tacos. The extensive liquor menu includes a great selection of tequilas and mezcals, along with whiskey. I decided to sip the house drink, the Berkshire Bramble, prepared with BMD Ethereal Gin, blueberry mint syrup, lime juice, and soda.

The Barn Kitchen & Bar

The Barn
Alexa Mellardo

The Barn is an ultra-cool, lively, and super convenient restaurant located right inside The Williams Inn. (Think fine dining meets relaxed, modern farmhouse.) My meal kicked off with champagne, followed by a scrumptious seared scallop dish, courtesy of the chef. I chose the grilled salmon with vegetable and lentil stew, sauteed spinach, and chive oil for my entrée, along with a decadent, warm apple tart for dessert—topped with vanilla ice cream and caramel sauce.

About the author

Tiara Clephin

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