Annual Events on Martha’s Vineyard

Annual Events on Martha’s Vineyard

When you’re planning a summer getaway, location is everything, and a stay with us means that you’re not only in the center of all the action in Woods Hole – you’re also just a short journey away to the picturesque island of Martha’s Vineyard. Many of our guests at the inn adventure over to the Vineyard for a day trip filled with stunning sightseeing, beaches, great food, relaxation, and so much more. Beyond its stunning natural landscapes and quaint seaside villages, the Island comes alive with a rich calendar of annual events that capture its unique spirit. From summer celebrations of culture and community, to exciting fall festivities, let’s embark on a journey through the enchanting annual events that make Martha’s Vineyard a perfect destination during your Cape Cod summer getaway.

Island Alpaca Shearing Day

As winter’s chill gives way to spring’s warmth, Martha’s Vineyard kicks off its annual seasonal events with Island Alpaca Shearing Day. Held in April, this event hosted by Island Alpaca Company in Oak Bluffs invites visitors to get up close to their pack of gentle, curious alpacas while enjoying hands-on and educational experiences about the fleece to fiber transition and the benefits of alpaca ownership. Fun for the whole family!

Annual Events on Martha’s Vineyard: Welcoming Spring and Mother’s Day Weekend

What better way to celebrate mom than with a family getaway to Martha’s Vineyard? During this annual celebration of spring and Mother’s Day, the charming town of Edgartown comes alive with special brunches, shopping experiences, scenic strolls, horse drawn carriage rides, and heartwarming moments shared with loved ones.

Taste of the Vineyard Food Festival

The month of June brings culinary delight with the Taste of the Vineyard, known by many as “The Taste”. Food enthusiasts gather on the grounds of the historic Daniel Fisher House to indulge in a delectable showcase of local flavors, wines, and handcrafted delicacies. This two-night occasion is the Vineyard Preservation Trust’s most important annual fundraiser. By attending, you are stewarding their work to preserve and care for the Island’s most iconic, historic landmarks, including the Flying Horses Carousel in Oak Bluffs, the nation’s oldest operating platform carousel!

Annual Events on Martha’s Vineyard: Oak Bluffs Harborfest

Celebrate the arrival of summer with Harborfest, a maritime celebration that takes place in June each year in the vibrant town of Oak Bluffs. Take the opportunity to walk, taste, and shop your way through town, while enjoying live music and plenty of waterfront festivities for all ages. Catch an Oak Bluffs-bound Steamship Authority ferry just a short walk from our inn and arrive steps from Oak Bluffs harbor!

Juneteenth

Juneteenth is more than just a single day on Martha’s Vineyard, it has become a weekend-long multicultural extravaganza of engaging speakers, music, food, and more! Local businesses, nonprofit organizations, and the Island community come together during this time each year to celebrate and honor African American culture and heritage. 

Annual Events on Martha’s Vineyard: First Friday Vineyard Haven

From June through October, First Friday in Vineyard Haven is a free community-inspired outdoor event that takes place on the first Friday of each month. Enjoy a night full of local art, music, food, and culture in Owen Park, a picturesque lawn with incredible views of the Vineyard Haven Harbor. Festivities also include gallery walks and late night shopping on Main Street. Catch a Vineyard Haven-bound Steamship Authority ferry just a short walk from our inn, and arrive just steps from Owen Park!

Fourth of July in Edgartown

Martha’s Vineyard goes BIG each year with their Independence Day celebration! The festivities kick off with the Edgartown 4th of July Parade, where the streets come alive with patriotic pride as floats, marching bands, and community groups march downtown. After the sun sets, enjoy a spectacular fireworks display over the stunning Edgartown harbor. 

Annual Events on Martha’s Vineyard: Tisbury Street Fair

The annual Tisbury Street Fair marks the town’s birthday, which is celebrated with a fun-filled block party on Main Street in early July. Join thousands of locals and visitors in supporting Tisbury’s local businesses while enjoying live music, delicious food offerings, souvenir shopping, and lots of family-friendly activities. 

Grand Illumination Night

Grand Illumination Night in Oak Bluffs is a cherished tradition held on the third Wednesday in August where thousands gather in the heart of Oak Bluffs to witness the illumination of colorful lanterns at the iconic Gingerbread Houses. This magical event harks back to the 19th century, paying homage to the Island’s unique history and a spirit of unity between Islanders and visitors alike. 

Annual Events on Martha’s Vineyard: Agricultural Fair

Candy apples, carnival rides, and adorable farm animals await at the West Tisbury Agricultural Fair! Every August, the Island comes together for four days to celebrate the Island’s agricultural roots during the third week of the month, Thursday through Sunday. Bring the whole family for a night full of competitive games, rides, livestock displays, and delicious treats. 

Oak Bluffs Fireworks

As summer draws to a close, don’t miss out on the spectacular fireworks display in Oak Bluffs during their annual fireworks celebration, typically held on the third Friday in August. Start the evening in picturesque Ocean Park and watch a live musical performance on the gazebo, then get ready for an exciting night of “oohs” and “ahs” as the colorful fireworks light up the night sky. It’s truly a stunning display!

Annual Events on Martha’s Vineyard: Beach Road Weekend

Beach Road Weekend treats music lovers to an eclectic three-day music festival, welcoming renowned artists from around the world for a weekend of unforgettable performances. Enjoy live music by world-renowned acts, good eats, great vibes, and fun for the whole family. This festival takes place at Veterans Memorial Park in Vineyard Haven every August. Previous headliners have included superstars like Beck, Wilco, Mumford & Sons, Leon Bridges, Bon Iver and many other big names!

Wind Festival

The annual Wind Festival in Oak Bluffs each September embraces the Island’s breezy charm with kite-flying, music, and interactive family activities. Held in Ocean Park, this event is fun for both adults and children alike, and is a playful reminder of the Island’s natural wonders. 

Annual Events on Martha’s Vineyard: MV Striped Bass & Bluefish Derby

As autumn approaches, the Striped Bass & Bluefish Derby takes center stage. For almost 8 decades, this legendary fishing competition draws anglers from far and wide to test their skills and enjoy the island’s scenic waters. Spanning from mid-September to mid-October, “The Derby” invites anglers to experience great fishing, rich history, making new friends, and generous sponsor-donated prizes. 

MV Food & Wine Festival

Discover the flavors of Martha’s Vineyard with the Island’s annual Food & Wine Festival! This culinary celebration in October brings together chefs, winemakers, and enthusiasts for tastings, workshops, and gourmet experiences that celebrate the Island’s rich and diverse flavors. 

The possibilities are endless for a day (or several!) spent on Martha’s Vineyard. From exploring charming towns to basking on sun-kissed beaches to participating in their many community events, every moment on the Island is a treasure. With its idyllic scenery and close-knit community, it’s a place where time seems to slow down. And as the sun sets on your day, the welcoming embrace of our Inn awaits, following a quick trip on the ferry. So pack your bags and book your next stay with us for an unforgettable Cape and Island adventure!