The Nantucket Wine Festival has blossomed into one of the nation's most celebrated wine and food events. Over 30 tastemakers have come together to celebrate their specialties from exquisite wines to delectable hors d’oeuvres. Come sip, savor and experience a spectacular food and wine event on Nantucket. NWF will be a fully vaccinated event. Proof of Vaccination is necessary to enter any and all NWF venues.

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.
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Built on Stilts Dance Festival
When: Aug 11 to Aug 11, 2022.Built on Stilts is centered on the equity inherent within the human body, around equal opportunities for every body on our stages and in our audiences. The festival is here for all voices, styles, sizes, ages, and beautiful shades of every dancing body.
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Annual Agricultural Society Fair
When: Aug 18 to Aug 21, 2022.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.
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Martha's Vineyard Oyster Festival
When: Oct 1 to Oct 2, 2022. Location: MV MuseumThe Martha’s Vineyard Oyster Fest (MVOF) is a mission-based festival that aims to drive long-term local, regional, and national awareness of Martha's Vineyard and Massachusetts-farmed oyster and native fish profiles. The festival gathers oyster farmers, the who’s who in the beverage industry, the area’s best chefs, and a fantastic cadre of special guests, to celebrate the bounty from the sea.
This cultural event marries food, wine, education, and music. Enjoy live chef demonstrations with native seafood, taste fresh shellfish from local oyster farms and dine on artisanl meals from food trucks along with beer and wine tastings.
A portion of the MVOF proceeds will go to the Martha’s Vineyard Shell Recovery Partnership. This MVSG program reduces and recycles shell waste on the Island, provides a local source of shell for shellfish restoration, and improves shellfish production, which in turn improves local water quality.
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Christmas in Edgartown
When: Dec 8 to Dec 11, 2022. Location: Martha's VineyardChristmas 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.
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Nantucket Wine & Food Festival
When: May 18 to May 22, 2022. Location: Nantucket -
Boston Pops on Nantucket
When: Aug 13, 2022. Location: NantucketCome 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.
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Annual Tim Russert Summer Groove Concert
When: Aug 20, 2022. Location: Nantucket -
Opera House Cup Regatta
When: Aug 21, 2022. Location: NantucketThe 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.
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Cranberry Harvest Festival
When: Oct 8, 2022. Location: NantucketDo you love cranberries? Then you'll love the Milestone Cranberry Bog and the Nantucket Conservation Foundation's Annual Cranberry Festival. Come out to the festival grounds and watch the berries being harvested, learn about the history of cranberry farming on Nantucket, participate in the family activities or just kick back and enjoy the music and the spectacular autumn scenery of one of the most unique and beautiful places on our Island. Don't forget to bring home a pound, or two, of Nantucket Cranberries for the Holidays!
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Annual Tree Lighting & Community Caroling
When: Nov 27, 2022. Location: NantucketEveryone gathers at the top of Main Street on Nantucket to watch over 100 Christmas trees come alive with color and light. Caroling follows, filling the air with sounds of an old fashioned Christmas. School children, youth groups and non-profit organizations join with island businesses to decorate the trees in time for Christmas Stroll the following weekend.
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Nantucket Christmas Stroll
When: Dec 2 to Dec 4, 2022. Location: Nantucket Main StreetNantucket's Christmas Stroll Weekend is enchanting and magical--a glittering Advent calendar come to life--transforming the island into an awe-inspiring panorama of sight and sound. Santa arrives via his nautical sleigh--with the help of the Coast Guard--and parades up Main Street to the Jared Coffin House, where he meets with children young and old to determine whether they've been naughty or nice. At the top of Main Street, the Magical Talking Tree mystifies children of all ages, and a Christmas Marketplace showcases the talents of local businesses--from foods and crafts to handmade wares and informational tables. Activities abound throughout Town, and there's even a Scavenger Hunt! There's no time machine needed to transport yourself back to Christmases past in this Charles Dickens' backdrop come to life. We invite you to celebrate with us