Memorial Day Weekend on Nantucket signals the official start of summer on this New England island. As the calendar turns toward the end of May, the historic Isle transforms from its quiet off-season slumber into a lively coastal destination. The weekend brings the famous Figawi sailing race, drawing thousands of sailors and spectators to the island’s shores.
Meanwhile, seasonal residents return to open their summer homes, restaurants unveil their seasonal menus, and shops along the cobblestone streets prepare for the influx of visitors eager to experience Nantucket’s unique mix of maritime heritage and upscale coastal appeal.
A Joyful Return: Welcoming Summer on Nantucket
The atmosphere during this holiday weekend is filled with excitement. Hotel Pippa and other island accommodations welcome guests ready to enjoy three days of sailing competitions, beach excursions, and local celebrations. The historic downtown area buzzes with activity as visitors stroll past gray-shingled buildings and blooming gardens that exemplify Nantucket’s distinctive architectural character.
For many islanders and regular visitors, this weekend represents more than just a holiday—it’s a cherished reunion with the island and its community after the quiet winter months, marking the beginning of another glorious summer season on this beloved island thirty miles out to sea.
Figawi Race Takes Center Stage in Holiday Festivities
The Figawi race is the centerpiece of Nantucket’s Memorial Day Weekend festivities. Early Saturday morning, spectators gather to watch skippers and their crews prepare their vessels for the competitive pursuit regatta. Beginning around 8 am, a spectacular parade of sailboats departs Lewis Bay, passing Kalmus Beach before congregating off the Hyannis Port jetty.
The race officially commences at 10 am, with boats navigating the 26-mile course across Nantucket Sound, eventually finishing at the entrance to Nantucket Harbor in a magnificent procession into the Boat Basin. Brant Point Light offers a great vantage point for those wanting to witness the colorful spinnakers and racing action.
Celebrations on Land: Community, Tradition, and Tribute
Beyond the sailing competitions, the island offers a wealth of activities throughout the holiday weekend. Sunday brings the Figawi Invitational, where local high school teams from across Cape Cod and the Islands compete in an exciting regatta that showcases young sailing talent. Visitors can walk the docks at Nantucket Boat Basin to admire the impressive fleet of vessels or explore downtown’s shops for island treasures and souvenirs.
On Monday, the Memorial Day Parade marches down Main Street, providing a moving opportunity to honor military veterans while celebrating the patriotic spirit of the community. This respectful observance reminds everyone of the true meaning behind the holiday weekend.
Island Adventures: Biking, Breweries, and Beachside Bliss
For those seeking to experience the island beyond the harbor, Memorial Day Weekend presents perfect opportunities for exploration and enjoyment. Renting bicycles allows visitors to venture through Nantucket’s charming villages with their manicured gardens and iconic hydrangeas beginning to bloom.
The island’s network of bike paths makes it easy to reach outlying attractions like Cisco Brewers, where beer and wine tastings are complemented by live music and food trucks in a festive outdoor setting. The island’s beaches, though perhaps still a bit cool for swimming, offer peaceful stretches of sand for walking, shell collecting, or simply relaxing with the sound of waves as company.
A Taste of the Season: Dining Delights and Nantucket Traditions
Culinary experiences form another highlight of the weekend, as most of Nantucket’s renowned restaurants reopen for the season, showcasing the freshest seafood and local produce. From casual clam shacks to upscale dining establishments, the island’s food scene springs to life during this weekend. Visitors should note that reservations are highly recommended, as tables fill quickly during this popular holiday period.
After dinner, a stroll downtown for ice cream at The Juice Bar represents a quintessential Nantucket tradition. As daylight extends into the evening, the mild late-May weather creates perfect conditions for outdoor dining, harbor-front cocktails, and reconnecting with family and friends against the backdrop of Nantucket’s undeniable summer appeal.
