6 Unmissable Annual Events on Cape Cod and the Islands

From oyster festivals and artisanal markets to live music and sailing, discover the best annual events that embody the spirit and heritage of Cape Cod, Martha’s Vineyard, and Nantucket.

Contrary to popular belief, life on Cape Cod and the Islands doesn’t halt from Labor Day until the summer tourists return over Memorial Day weekend. Year-round events and festivals celebrate the culture and traditions of this scenic slice of New England, honoring artisans, farmers, and musicians. Whether visitors are enticed by seafood, art galleries, wine tasting, or luxury yachts, these six events are not to be missed.

Daffodil Festival

Nantucket - April

The Nantucket Daffodil Festival, hosted by the Nantucket Garden Club on the last weekend of April, is a vibrant celebration of spring. With festive attire, street parades, and a flower show at Bartlett’s Farm, the event culminates in a daffodil-adorned antique car parade from Main Street to a tailgate picnic in Siasconset. This festival marks the official arrival of spring on the island.

Nantucket Wine and Food Festival

Nantucket - May

Held in early May, the Nantucket Wine & Food Festival showcases around 600 wines from 150 wineries worldwide. Established in 1996, this event highlights Nantucket’s prestigious culinary scene and attracts a crowd keen on savoring fine wines and gourmet food.

Juneteenth

Martha’s Vineyard - June

Celebrated as America’s second Independence Day, Juneteenth commemorates the abolition of slavery in the US. Martha’s Vineyard’s Juneteenth Jubilee includes the arrival of the Amistad ship, a gospel brunch in Edgartown, and the Annual Juneteenth Jubilee Cultural Festival in Oak Bluffs. This event celebrates the island’s historical support for the abolition movement and its significance as a getaway for black families.

Love Local Fest

Cape Cod - July and September

The Love Local Fest, held three times a year in Hyannis’s Aselton Park, showcases Cape Cod’s artists, farmers, and small business owners. This free event allows visitors to engage with the local community and support the vibrant year-round economy of the peninsula.

Wellfleet OysterFest

Cape Cod - October

Celebrating Cape Cod’s renowned oysters, the Wellfleet OysterFest honors the local harvest with live music, arts and crafts, and an abundance of oysters. Held in October, this festival is a testament to Wellfleet’s historical significance in the commercial oyster industry.

A Very Vineyard Holiday

Martha’s Vineyard - December

Kicking off on Thanksgiving Day, A Very Vineyard Holiday transforms Martha’s Vineyard into a winter wonderland. With holiday decorations, the Christmas in Edgartown Parade, wreath-making workshops, and the Artists in Residence Holiday Market, this event offers an intimate and festive experience after the summer crowds have departed.