A Refined Weekend at the Greenport Maritime Festival
Each September, Greenport transforms into a salt-sprayed celebration of its nautical past. The 2025 Greenport Maritime Festival, September 20th & 21st, promises a weekend of tall ships, waterfront parades, local flavors, and coastal charm that draws thousands from across the East End and beyond.
Presented by the East End Seaport Museum, the 35th annual festival is more than just a nod to Greenport’s shipbuilding roots. It’s a full-throttle immersion into maritime culture, where schooners anchor in the harbor, oyster shuckers line the streets, and sea shanties float on the breeze.
The 2025 lineup features the return of the Tall Ships, the Fireboat John J. Harvey, and the ever-popular cardboard boat regatta, which is a mix of teamwork and comedy. Friday night kicks things off with the Land & Sea Gala—a ticketed waterfront tasting event at the Safe Harbor Marina, pairing local wines with seafood from top area chefs. Saturday’s Merry Merfolk Parade is a pageant of pirates, fire trucks, vintage tractors, and local floats, while Sunday leans slower, ideal for strolling, sipping, and taking it all in.
The festival may celebrate boats, but Greenport itself has become a destination far beyond the harbor. A magnet for food lovers and culture seekers, the village offers plenty of reasons to linger. For a spirited start to the day, Crazy Beans serves brunch and cocktails inside the historic Greenport Coronet Luncheonette on Front Street, a North Fork landmark since the 1950s. Bruce & Son on Main Street is an ideal introduction to Greenport’s culinary ethos: thoughtful, local, and quietly refined. Their lemon ricotta pancakes, and house-made pastries feel almost too pretty to eat.
After a morning by the marina, pop into Little Creek Oyster Farm & Market for shuck-your-own oysters and a local beer, or snag a lobster roll at Claudio’s Waterfront, an institution perched above the bay with unbeatable views and a legacy dating back to 1870.
Evenings call for something quieter. The Frisky Oyster remains a standout—its design sleek, its lighting low, its menu daring yet grounded in coastal ingredients. Meanwhile, American Beech—housed in a restored 19th-century building—offers an indoor-outdoor dining experience that feels both intimate and celebratory.
And of course, no trip to the North Fork is complete without a stop at one (or several) of the region’s wineries. Kontokosta Winery, just a short walk from downtown, offers sweeping bluff-top views and a glass of crisp Albariño or rosé that perfectly complements the briny air. Nearby, One Woman Wines & Vineyards delivers intimate tastings in a countryside setting, while Macari Vineyards—a short drive west—pairs biodynamic wines with panoramic vineyard views.
Whether you come for the boats, the buzz, or the bounty of land and sea, the Greenport Maritime Festival remains one of the East End’s most anticipated weekends—a celebration of tradition, tide, and the tight-knit community that keeps it all afloat.
Where to Stay: Elevated Escapes in and Around Greenport
The Menhaden
207 Front Street
Stylish, central, and service-focused. Located just steps from the marina, The Menhaden is Greenport’s boutique crown jewel. With clean, coastal-modern interiors, concierge-curated experiences, and a rooftop deck offering panoramic harbor views, it’s ideal for festival-goers who want both proximity and polish. Guests can also take advantage of the property’s house bicycles and beach shuttles to explore the North Fork at their own pace.
The Harbor Front Inn
209 Front Street
Unfussy luxury on the water’s edge. This classic waterfront property offers spacious rooms with balconies that open directly to the harbor breeze. Its location—right on Front Street—places you in the heart of the festival while maintaining a sense of retreat. The vibe is understated and relaxed, with an emphasis on comfort and quiet views.
American Beech HoteL
302 Main Street
Artful elegance meets Greenport cool. Tucked within Stirling Square, American Beech blends moody tones, custom art, and cosmopolitan energy with village charm. Each suite is uniquely styled, and the on-site restaurant and cocktail bar keep the vibe lively into the evening. It’s perfect for travelers who appreciate both aesthetic edge and walkable convenience.
Sound View Greenport
58775 County Road 48
Mid-century charm with a private shoreline. Just outside the village, Sound View offers serene, sea-facing rooms literally steps from the sand. The hotel’s updated interiors nod to its 1950s roots while delivering modern design and amenities. Onsite restaurant The Halyard offers fine dining with sweeping views of the Long Island Sound, and the outdoor saltwater pool seals the deal for a laid-back luxury experience.
Hotel Moraine
62005 County Road 48
North Fork luxury family resort. Featuring thoughtfully designed guestrooms perched upon a bluff overlooking the Long Island Sound. The property is inspired by nature and the primitive coastline of the Long Island Sound. Providing signature North Fork touches to make you feel at home while offering local experience and exceptional service.
For more information visit: eastendseaport.org
Photos: East End Seaport Museum
