It’s true — as the colder months settle in, many favorite island spots take a well-earned break. But don’t let the quiet fool you. While much of the island slows down, there are still plenty of places that stay open on Martha’s Vineyard all winter long. From cozy cafés and comfort food to indoor activities and local shops, winter here has its own kind of charm. Whether you’re a year-round resident or just visiting for an off-season escape, you’ll find welcoming spots to eat, explore, and enjoy even in the heart of winter.
Offshore Ale Co
Nestled in Oak Bluffs, Offshore Ale Co isn’t just about crafting the finest local brews – though their beers are indeed legendary. It’s also a haven for foodies craving mouthwatering pizzas and hearty fare. Picture yourself sinking into a booth, savoring each bite of their delectable pies while sipping on a pint of their signature ale. Pure bliss.
Sweet Life Café
Oak Bluffs welcomes back Sweet Life Café with open arms, as it now extends its culinary prowess throughout the winter months. Renowned for its exquisite cuisine and inventive cocktails, this top-tier restaurant adds a touch of sophistication to any evening out. Whether you’re craving a perfectly seared steak or a creatively crafted cocktail, Sweet Life Café delivers.
Chowder Company
Craving a taste of the island’s signature dish? Look no further than Chowder Company. Their award-winning clam chowder is a must-try, but this spot offers much more than just soup. It’s a laid-back locale where you can unwind over dinner and perhaps catch some live music upstairs at The Loft. A quintessential Martha’s Vineyard experience awaits.
Reliable Market
For those seeking provisions for a cozy night in, Reliable Market in Oak Bluffs is your go-to. This local supermarket stocks everything you need, from fresh produce to premium meats and dairy. Don’t forget to swing by their in-store bakery and deli for some tempting treats.
Winston’s
Spice up your winter dining adventures with a taste of the Caribbean takeout at Winston’s. This year-round hotspot serves up inspired dishes bursting with flavor – think mouthwatering jerk and curry delights. With Winston’s, every meal is an exotic culinary journey right in the heart of Martha’s Vineyard.
The Barn Bowl & Bistro
Don’t let winter’s chill keep you inside! The Barn Bowl & Bistro is open year‑round on Martha’s Vineyard, offering a lively bistro and bar plus a boutique 10‑lane bowling alley, making it a perfect indoor destination for cold or rainy winter days.
Want to Know What Else Is Open? For the most up‑to‑date listings of restaurants, shops, and services open throughout the off‑season, be sure to check out What’s Open on MV. This handy resource is updated regularly and makes it easy to see which local spots are open now all across the island.
Stay at Surfside Hotel
Once the Martha’s Vineyard winter is over, you’ll need a cozy place to unwind. Book a room at Martha’s Vineyard Surfside Hotel when planning to visit Martha’s Vineyard! Nestled in the heart of Oak Bluffs, our dog-friendly hotel is one of the premier lodgings in the area. Choose from accommodations with ocean-view rooms, garden views, modern amenities, and enough space for the entire family. We are a short four-minute walk from Ocean Park and a convenient location for exploring the rest of the island!
Our seaside accommodations are proud to be family-owned and operated since 1987. We look forward to welcoming you and your family to your home away from home at Martha’s Vineyard Surfside Hotel. Book your vacation with us today!