We’re often being asked by visitors and new residents “what is there to do on Martha’s Vineyard in the winter?” While many of our businesses are seasonal and won’t reopen until the spring, there are ample businesses that remain open throughout the year to keep us Island residents and visitors well-fed, inspired and entertained. We recently set about exploring Oak Bluffs one afternoon and were reminded of the many opportunities for excitement and enrichment in this colorful town, even in the winter months. Here we go, what to do in Oak Bluffs during the winter on Martha’s Vineyard.
What To Do In Oak Bluffs During The Winter On Martha’s Vineyard – Check Out The Barn Bowl and Bistro
One part restaurant, one part bowling alley, and one part private event/community space, you can feel the beat of The Barn Bowl and Bistro all year through. Many locals flock to the lanes each week as part of The Barn’s league bowling, and there are regular options for drop-in and bowling by reservation too. Families and friends gather here for a wide selection of well-priced meals and a spacious dining room that can accommodate large parties and special events. This winter the Oak Bluffs library is hosting Paint Nights at The Barn, an opportunity for individuals to come together to create masterpieces over cocktails, how fun! Look out for The Barn’s daily specials and if you’re into Trivia, get there on Mondays at 6:30 pm!
What To Do In Oak Bluffs During The Winter On Martha’s Vineyard – Savor the Sweet Life at The Sweet Life Cafe
Just up the street from The Barn Bowl & Bistro is The Sweet Life Cafe, a warm and inviting space that envelops you like a big warm hug upon entering. Saddle up to the bar for a glass of wine from their extensive wine list or make a dinner date of it. At the helm of the kitchen is Chef-Owner Hal Ryerson who is constantly innovating upon his New American menus based on what our local Island farmers and fishermen have available. Sunday brunch is extra special under the heated tent of their gorgeous patio and on Thursday Nights you can be treated to the sounds of local pianist Jeremy Berlin. How sweet it is!
What To Do In Oak Bluffs During The Winter On Martha’s Vineyard – Boogey on Down to The Ritz
If music and nightlife are what you’re after The Ritz is the place to be, and one of the only places to be on Martha’s Vineyard in the winter. This historic dive bar is the go-to venue for live music and revelry 12 months a year. Try your luck at karaoke or trivia on Tuesdays and enjoy live music from some of the Island’s most beloved bands Wednesday through Saturday in January. New in 2022 The Ritz is also home to Nina’s Dine and Dash which serves Brazilian fare packed with flavor.
Be Enchanted by the Oak Bluffs Gingerbread Cottages
The charm of the gingerbread cottages of the Martha’s Vineyard Camp Meeting Association is always in season! This time of year you can meander through the historic cottages, admiring the brightly colored homes and their intricate wooden trim, at a leisurely pace and appreciate them all to yourself. As you walk about imagine how the area has transformed from a religious tent campground dating back to 1835 to the adorable landmarks they are today. To learn more about the Oak Bluffs Campground check out our Martha’s Vineyard Bucket List post all about it. And be sure to mark your calendar for this year’s Grand Illumination event!
Stroll Along Oak Bluffs Harbor
Enjoy a scenic stroll along Oak Bluffs harbor and soak in the serenity it offers this time of year, with views of Vineyard Sound and the quiet homes that dot the coastline. While many of the boats have departed and the surrounding businesses have shuttered for the season, Winston’s Kitchen along the west side of the harbor is a year-round take-out operation in full swing. Winston’s serves breakfast, lunch, and dinner in generous portions six days a week, Tuesday through Sunday. Don’t miss their fried chicken! The owners of Winston’s Kitchen also recently took over Circuit Ave mainstay Linda Jean’s and we’re excited to see what the next chapter holds for the esteemed eatery.
Shop Year-Round Stores on Circuit Avenue
When it comes to retail, Circuit Avenue has several year-round shops and shopkeepers ready to assist with your next purchase. Basics Clothing Company is the go-to spot for clothing and footwear for the whole family, including big-name brands like Columbia, Carhartt, Helly Hansen, and more. Jewelry lovers can rejoice in knowing that Stefanie Wolf Designs is open all winter long, stocked with beautiful versatile pieces, plus clothing, accessories, and gifts galore. The holidays might be over but there’s always someone to buy for and Stefanie’s shop will not disappoint. When it comes to shopping local for life’s everyday staples, Reliable Market and Phillips Hardware have long offered year-round hours–and service with a smile.
What To Do In Oak Bluffs During The Winter On Martha’s Vineyard – Take Up a New Hobby
Did you make a resolution to try something new this year? Oak Bluffs is the place to discover new passions and dive into new projects. Enrich your winter by taking a class at Featherstone Center for the Arts, with options across ceramics, drawing, painting, jewelry, and more. Look out for their Art Nights, a series of fun evenings intended to get people out of the house and over to Featherstone to explore their creative side. The Oak Bluffs Library is another mecca for stimulating one’s curiosity, and its programming calendar includes crafts, game nights, dance lessons, and more!
If you’re on Martha’s Vineyard this winter make the most of these quieter days by getting out and mingling with friends and neighbors while supporting our local year-round businesses. And if an Oak Bluffs summer vacation is in the cards this year we’ve got plenty of Oak Bluffs Vacation Rentals still available. Email or call us today at 508-627-4567 ext 2 to find your perfect home away from home!
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