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Join others with similar interests at food and wine festivals, local cooking challenges, art classes, and community dances on the Island. Enjoy your meal with water views, next to a cozy fireplace, or at a hip and modern bar or lounge. One-of-a-kind boutiques, spas, and a richly diverse culture scene, including art galleries and quality theaters, provide endless hours of relaxation and entertainment.

Since there are no chain hotels, each accommodation welcomes you in their own unique way to give you an authentic Island experience. Each of the six towns offer their own brand of hospitality, and all are enchanting and engaging. Family-friendly activities include street fairs, fireworks, farmers markets, the Agriculture Fair, day camps, and festivals of art and music — and all offer the promise of lifelong memories.

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Families enjoy the pristine beaches and overall kid-friendly atmosphere of the Island. The numerous public beaches along the north shores allow younger kids to swim in wave-free waters, while the ocean beaches on the south shore are a favorite among teenage kids. The five historic lighthouses are unique in personality, and the Edgartown, East Chop and Gay Head lighthouses are open to visitors, and an adventure out to the Cape Poge Lighthouse is truly a one-of-a-kind experience for kids of all ages.

Plus, this treasured carousel has been enjoyed by Vineyarders and visitors for more than a century. While in Oak Bluffs, visit the colorful gingerbread cottages at the Tabernacleor enjoy a family picnic in the park! There are also pet-friendly options for families with furry members! Moonlight kayak tours, LED standup paddle boarding with disco-style lights, wind surfing and boarding, classic aviator plane rides in the Red Plane, daytime fishing trips, sunset sails, multiple road races throughout the year, bicycling through forest trails or paved paths!

Get the latest information on the Annual Spectrum Film Festival here! For Families: Each of the six towns offer their own brand of hospitality, and all are enchanting and engaging.