Annual Events

Our Favorite Martha’s Vineyard Summer Events

If you’ve ever dreamed of the perfect New England summer—think salty air, small-town charm, and something magical happening around every corner—Martha’s Vineyard is where it all comes to life. Summer 2026 is shaping up to be one for the books, and we’ve rounded up our absolute favorite events you’ll want to pencil in. June 7-9: […]

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Top 5 Martha’s Vineyard Fall Events You Can’t Miss This Year

As the vibrant summer days give way to the crisp air of fall, Martha’s Vineyard comes alive with a variety of events that capture the island’s unique charm and spirit. This autumn, the Vineyard is packed with exciting festivals and celebrations that promise something for everyone. From arts and film to family fun and Halloween […]

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A Dazzling Guide to Illumination Night Oak Bluffs

Every year, on the third Wednesday in August, Martha’s Vineyard transforms into a scene straight out of a fairytale. The annual Illumination Night Oak Bluffs is a summer staple that enchants both locals and visitors with its breathtaking display of thousands of colorful Japanese lanterns adorned on the iconic Gingerbread Houses. This magical evening is […]

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Our Favorite Martha’s Vineyard Festivals to Attend This Year

As the island gears up for a spectacular year of celebrations, we’ve curated a list of our favorite Martha’s Vineyard festivals that promise a deep dive into the soul of our picturesque island. Join us on this journey through the lens of the Martha’s Vineyard Film Festival, the savory notes of the Martha’s Vineyard Food […]

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Embrace Love and Inclusion: Your Ultimate Guide to Oak Bluffs Pride 2023

Welcome to Oak Bluffs, the perfect destination to celebrate Pride Month 2023! This beautiful town on Martha’s Vineyard is excited about the upcoming Oak Bluff Pride Parade, drag brunches, and the Spectrum LGBTQ Film Festival. Whether you’re a local or a visitor, there’s something for everyone to enjoy and celebrate. Oak Bluffs Pride 2023 is […]

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How to Celebrate the Holiday Season in Martha’s Vineyard

The temperature is getting colder, and winter is approaching on Martha’s Vineyard! Chillier weather brings new opportunities for our island town, especially during the holidays. Martha’s Vineyard is illuminated with thousands of twinkling lights, bringing a sense of magic during the season. Get bundled up and discover the holiday season on Martha’s Vineyard! Annual Holiday […]

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Martha’s Vineyard Events to Attend this Summer

When visiting Martha’s Vineyard, hitting up the beach may be the first thing on your itinerary. We really cannot blame you! Taking a swim in crystal-clear water or hanging in the white sand is always fun. But as warmer weather approaches, more unique and fun Martha’s Vineyard events are at your fingertips!  From music festivals, […]

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6 Fun Winter Activities to do on Martha’s Vineyard

mmer, some of the popular seasonal businesses shutter their doors until the following spring. Fortunately, there are a few good ones that stay open! Come on out to our island for a winter weekend getaway. You’ll find that there’s plenty of fun to be had during the off-season. Stay busy with these winter activities to do on Martha’s Vineyard.

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Top Things to do in August in Oak Bluffs MA

Not only is Oak Bluffs home to the largest marina on Martha’s Vineyard, but it’s also home to some of the most popular summer events. We’re gearing up for our biggest month in the summer with these events and things to do in August in Oak Bluffs, MA. Oak Bluffs Fireworks Who says fireworks are […]

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