6 unmissable annual events on Cape Cod and the Islands 

Contrary to popular belief, life on Cape Cod and the Islands doesn’t come to a complete halt from Labor Day until the summer tourists return over Memorial Day weekend. Events and festivals in this corner of Massachusetts are held throughout the year, honouring diverse local groups such as artisans, farmers and musicians. These annual affairs celebrate the culture and traditions of each location and the passions of the people who call this scenic slice of New England home. Whether visitors are enticed by seafood, art galleries, wine tasting or even luxury yachts, these are six events not to miss.

1. Daffodil Festival

Nantucket - April 

Who needs tulip season in Holland — or cherry blossoms in Japan, for that matter — when you have the vivid colours and fresh springtime energy of the Nantucket Daffodil Festival? The Nantucket Garden Club hosts this annual event on the last weekend of April, which is now in its 48th year. The festival acts as a ceremonial brightening of an island otherwise known as ‘The Grey Lady’ for its famous fog.

Think festive attire, street parades and revelry. Attendees’ outfits rival the vibrant pastel blooms on display at the themed flower show at Bartlett’s Farm. Later, a daffodil-adorned antique car parade sets out from Main Street to a tailgate picnic in Siasconset. After which, springtime on the island — a notoriously tardy season in coastal New England — has officially sprung.

2. Nantucket Wine and Food Festival

Nantucket - May

Consider the Nantucket Wine & Food Festival a more mature yet equally lively version of Figawi, the hedonistic Memorial Day weekend sailing race that unofficially heralds the start of the summer season. The wine and food festival, established in 1996, occurs in early May and is frequented by a more local (or summer local) crowd. Its growth and prominence over the past couple of decades reflect Nantucket’s increasingly prestigious culinary scene, with around 600 different wines from 150 wineries around the globe on show — not bad for an island only 14 miles long.

3. Juneteenth

Martha’s Vineyard - June

Known as America’s second Independence Day, Juneteenth was recognised as a federal holiday in 2021 to commemorate 19 June 1865, when slavery was finally abolished in the US. The Juneteenth Jubilee on Martha’s Vineyard is a weekend-long multicultural extravaganza marked by the arrival of Amistad (a replica of the historic ship that was the setting for the slave revolt in 1839) in Vineyard Harbor, gospel brunch in Edgartown and the Annual Juneteenth Jubilee Cultural Festival at the Tabernacle in the town of Oak Bluffs.

Martha’s Vineyard has a storied history in the fight for freedom, demonstrating support for the abolition movement as early as 1787, when John Saunders, a former slave and preacher, introduced Methodism to Oak Bluffs. The neighbourhood — and the island at large — has remained a celebrated getaway for black families for centuries.

4. Love Local Fest

Cape Cod - July and September

The Love Local Fest showcases the artists, farmers and small business owners who make Cape Cod vibrant year-round. The event is free and open to the public and held three times annually in Hyannis’s Aselton Park — on the last Sunday in July and September and the first weekend of December. The festival is the perfect opportunity for visitors to engage with the local community and give back to this picturesque peninsula, which may be a seaside holiday destination for some, but is a home for many.

5. Wellfleet OysterFest

Cape Cod - October

While many towns in New England would like to claim they produce the tastiest oysters, Wellfleet’s salty supremacy is rarely disputed — a consensus reached centuries ago. Commercial oyster fishing in the US began in this Barnstable town in 1665, and by the mid-1800s, Wellfleet was considered the oyster capital of the world. So, what better way to celebrate Cape Cod’s most magnificent molluscs than by attending the Wellfleet OysterFest to honour the local harvest? Live music, arts and crafts, endless oysters and a shuckin’ good time awaits.

6. A Very Vineyard Holiday

Martha’s Vineyard - December 

Deck the halls in true island style with A Very Vineyard Holiday, a month-long celebration on Martha's Vineyard. The island transforms into a winter wonderland with its downtown shops adorned with holiday decorations. Plus, the summer crowds have departed, making it a more intimate and jolly experience. The roster of events includes the Christmas in Edgartown Parade, wreath-making workshops, the Artists in Residence Holiday Market and more.