Not many realize that Martha’s Vineyard is a year-round destination. While summer is the most popular time to visit, each season brings about its own reason to stay on the island, and the town of Oak Bluffs is no exception. Discover our seasonal guide to Oak Bluffs, Martha’s Vineyard, and find your favorite time to visit!
Spring
Springtime on Martha’s Vineyard brings warmer temperatures, spring flowers, Sunday brunches, and Easter egg hunts all over the island. Businesses that shut down in winter begin reopening in preparation for summer, and people emerge from winter hibernation.
One of our favorite things to do in the spring in Oak Bluffs is stroll through the Oak Bluffs Campground. While you can visit any time of year, the famed gingerbread houses are the most beautiful in the spring, with all the fresh floral blooms and new spring greens popping up. The gingerbread cottages at the Oak Bluffs Campground are an iconic attraction here. The 19th-century cottages feature delicate trim, picket fences, and colorful details, all with the look of storybook gingerbread houses.
Summer
Summer is by far the most popular time to visit Martha’s Vineyard. Warm sunny days and long summer nights bring fun festivals and relaxing days at the beach. Crowds gather along Circuit Avenue for shopping, dining, and nightlife while the beaches fill up during the day for endless summer fun.
Martha’s Vineyard beaches are known for their unspoiled charm, scenic landscape, and beautiful views. The Oak Bluffs Town Beach, also called Inkwell Beach, is a popular spot in the summer. At the heart of town and with views of Nantucket Sound, it’s a great place to spend your summer days.
Summer in Oak Bluffs kicks off with the annual Oak Bluffs Harborfest and goes out with a bang in August, with some of the most popular summer events on the island, including the Grand Illumination Night and the Aggie Fair.
Fall
There are many reasons to visit Martha’s Vineyard in the fall, from the colorful fall foliage to the many autumn festivals. Plus, you’ll notice the busy hustle and bustle of summer beach-goers has died down, allowing visitors to enjoy more of the island they love.
A famous fall festival on the island is Tivoli Day in Oak Bluffs. Join us as we wave goodbye to summer with our street fair and block party. Tivoli Day is an old-fashioned September festival in downtown Oak Bluffs and has been an island tradition for four decades. Enjoy live entertainment, street vendors, dancing, arts, end-of-summer sales, food, and more food. It is typically held the weekend before the first day of autumn.
Fall is also a great time to visit Mocha Mott’s. A local favorite, this little coffee shop serves organic and fair-trade coffee, espresso drinks, baked goods, and other tasty treats. Located on Circuit Avenue in the heart of Oak Bluffs, it’s a great place to enjoy the cool fall weather with a hot cup of joe.
Winter
Winter on Martha’s Vineyard brings about much colder temperatures and snow but also fewer crowds and beautiful snow-capped scenery. Settle into cozy accommodations at Martha’s Vineyard Surfside Hotel, explore the island’s beautiful trails, dine in or take out from some of the year-round restaurants, and grab your camera to capture beautiful wintery scenes of the island.
One of our favorite things to do in the winter is photographing the island’s lighthouses. Visit Oak Bluffs’ East Chop Lighthouse for some stunning winter photos. Or take your camera with you while you explore many of the area’s open trails.
Discover our favorite winter activities on Martha’s Vineyard.
Stay at Martha’s Vineyard Surfside Hotel
When planning a visit to Oak Bluffs Martha’s Vineyard this year, book a stay at Martha’s Vineyard Surfside Hotel! 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!