Event Calendar

Martha’s Vineyard Event Calendar

The captivating Island of Martha’s Vineyard occupies a special place in the hearts and souls of both its year-round population and diverse visitor base. Whether you’re seeking the quiet and solitude of nature, looking for a festive cultural experience, or both, Martha’s Vineyard offers it all.

The Island’s year-long calendar of events entices visitors to come back again and again—for a day trip or an extended stay. And remember, it's easy and convenient to book your Steamship Authority reservations online.

  • Martha's Vineyard Comedy Fest

    When: Jul 31 to Aug 4, 2023.

    This comedy festical features the depth and breadth of current and past African American comedians, writers, promoters, club owners, and supporters.

  • Annual Seafood Buffet & Auction - Virtual event

    When: Jul 6, 2023.

    In support of sailing, rowing, and maritime education on the Island.

    For more than a quarter of a century Sail MV’s annual Seafood Buffet & Auction has been a highlight of the Vineyard summer season. Consider supporting the Virtual Seafood Buffet & Auction by purchasing tickets or a table. Auction items include sailing trips aboard classic local vessels. 

  • Sail MV Vineyard Cup Regatta

    When: Jul 7 to Jul 9, 2023.

    This 2-day race is held annually on the waters of Nantucket Sound and Vineyard Sound off the Island of Martha’s Vineyard. Sail Martha’s Vineyard is the Organizing Authority and invites all to come and enjoy a great blend of sailing and fun.

  • Annual Possible Dreams Auction

    When: Jul 23, 2023.

    The Possible Dreams Auction benefits Martha’s Vineyard Community Services.  The idea for an 'unbuyable opportunities' auction was brought to Community Services by Sandy Ray, then chair of the Fundraising Committee. The Possible Dreams Auction is one of the oldest, most enduring celebrity concept auctions. The Auction Committee has raised over $8 million dollars in support of unfunded care provided by the five programs of Martha’s Vineyard Community Services.

  • Grand Illumination

    When: Aug 16, 2023.

    Grand Illumination

    One very special highlight of the summer season on the Oak Bluffs Campground is Grand Illumination. The famous gingerbread cottages are adorned with colorful Chinese and Japanese lanterns, and both a Community Sing and a band concert are held in the Tabernacle.   Grand Illumination started in Oak Bluffs over a century ago and was initially intended as a way of marking the visit of the Governor of Massachusetts.

  • Annual Agricultural Society Fair

    When: Aug 17 to Aug 20, 2023.

    The Martha's Vineyard Agricultural Society was established in 1859. It promotes the pursuit of agriculture, horticulture, land conservation, youth activities, mechanic and domestic arts and encourages the raising and improving of plant and animal stock and the sale of island-grown produce and flowers at local farmers' markets.

    The Society, which has over 1000 year-round and seasonal members, is perhaps best known for its annual Agricultural Fair, which attracts thousands of islanders and visitors each summer.

  • MV International Film Festival

    When: Sep 5 to Sep 10, 2023.
  • Martha's Vineyard Wind Festival

    When: Sep 9, 2023. Location: Ocean Park Oak Bluffs

    MV Wind Festival

    Kite flying and making, Frisbee games, model sailboat racing, live music, and more! All events are at Ocean Park in Oak Bluffs, MA. This is a free event with no registration fees. 

  • Christmas in Edgartown

    When: Dec 7 to Dec 10, 2023. Location: Martha's Vineyard

    Christmas in Edgartown

    Christmas in Edgartown is a weekend festival you don’t want to miss! Every year through the various events, Christmas In Edgartown helps raise over $50,000 for island-wide charities and non-profits. Come be apart of the holiday magic!

Nantucket Event Calendar

Fondly nicknamed the “Grey Lady”, Nantucket is an enticing mecca of charm and distinction. From the cobblestone streets and sea captains’ mansions of Nantucket town, to the rose-covered cottages of Sconset, to the panoramic wind-swept moors, pristine beaches and ocean vistas, you will find Nantucket to be the perfect antidote to the hectic demands of modern life.

Once the whaling capital of the New World, today the Island attracts visitors year-round with its natural tranquility, delightful traditions, fine dining, and premier cultural events. Remember, it's easy and convenient to book your Steamship Authority reservations online.

  • Figawi Race Weekend

    When: May 26 to May 29, 2023. Location: Nantucket

    Figawi Race











    The Annual Figawi Race Weekend is recognized as a top sailing event not only on the East Coast but is known nationally as well as internationally. Figawi Race Weekend kicks off the Cape Cod and Nantucket summer season. Entries include sailors from several states 240+ boats (including 30 power boats.) Over 3,000 sailors and visitors, as well as locals, attend this event.

  • Sam Sylvia Pro-Am Golf Tournament

    When: Jun 4 to Jun 5, 2023. Location: Nantucket

    Participants select their own threesomes, and play with a professional from the New England PGA. This special event kicks off with a cocktail party, on course golf games and auction on Sunday evening. The tournament will be played Monday morning at Sankaty Head Golf Club, followed by an awards luncheon.

    All proceeds benefit the Nantucket Boys and Girls Club. If you are interested in playing in this year's tournament or sponsoring the tournament, please call 508.228.0158.

  • Nantucket Book Festival

    When: Jun 15 to Jun 18, 2023.

    The Nantucket Book Festival is a multi-day cultural event celebrating the rich literary resources of Nantucket’s past, present and future. The Festival seeks to create and renew enthusiasm for books, connect authors and readers, encourage a love of reading and writing among young people, raise funds for literary causes, and promote Nantucket Island as an oasis and haven for the literary arts.

  • Nantucket Film Festival

    When: Jun 21 to Jun 25, 2023. Location: Nantucket

    One of the premiere destination film festivals in the world, visitors come from all over to experience our preview screenings, signature programs, and stand out hospitality on a magical island rich with history, a friendly atmosphere, and beautiful sandy beaches.

  • Fourth of July Celebration

    When: Jul 4, 2023. Location: Nantucket

    Jetties beach is the best place in Nantucket to view fireworks and celebrate the Independence Day. Each year, families and friends set up on the beach at Jetties beach and marvel at the spectacular fireworks show, over the harbor. The amazing firework display is very popular and draws quite a crowd. Leading up to the fireworks at night, there are many activities to take part in throughout the day. A fun, annual event is the 4th of July parade through Main St. This family oriented event is highlighted by a water fight featuring local fire trucks, supplying lots of water.

  • Nantucket Comedy Festival

    When: Jul 13 to Jul 15, 2023. Location: Nantucket

    Founded in 2007, the Nantucket Comedy Festival is an annual summer event that brings top comedic talent to Nantucket Island as the major fundraiser for Stand Up & Learn, an island-based, year-round comedy education program serving Nantucket's children. The Nantucket Comedy Festival envisions Nantucket as a community connected by laughter.

  • Nantucket Triathlon

    When: Jul 15, 2023. Location: Nantucket

    Nantucket Triathlon

    The Steamship Authority is proud to be the official transportation sponsor of this USAT sanctioned event. Register to compete or cheer on your favorite athlete as they  swim in the waters of Nantucket Sound, and then bike and run on the beautiful island of Nantucket. Part of all proceeds benefit The Town of Nantucket Scholarship Fund.


  • Nantucket Race Week

    When: Aug 12 to Aug 20, 2023. Location: Nantucket

    Nantucket Race Week is nine days of regattas, awards ceremonies, and parties hosted by Nantucket Yacht Club and Great Harbor Yacht Club to benefit Nantucket Community Sailing. Nantucket Race Week is proud to be a Clean Regatta as certified by Sailors for the Sea. 

  • Boston Pops on Nantucket

    When: Aug 12, 2023. Location: Nantucket

    Come and enjoy the annual Boston Pops on Nantucket concert to benefit Nantucket Cottage Hospital with outstanding music and fireworks in a gorgeous setting on Jetties Beach.

  • Opera House Cup Regatta

    When: Aug 20, 2023. Location: Nantucket

    The Opera House Cup Regatta is a cherished tradition, held on the third Sunday of August on Nantucket. The Opera House Cup Regatta was the first all-wooden, single-hulled classic boat regatta on the East Coast, and it attracts some of the finest sailboats in the country.