This North Fork village on Long Island has a working harbor, 19th-century buildings, and family-owned wineries. A historic carousel spins near local seafood spots.
Greenport, settled in 1682 on Long Island's North Fork, holds onto its maritime history with a working 1844 train station and ferry routes to Shelter Island. Walk Front Street to see a 1920s carousel spinning near Mitchell Park’s harbor edge, or explore the East End Seaport Museum’s exhibits on whaling tools and shipbuilding logs. Converted oyster warehouses along the waterfront now hold art studios, shops selling handmade pottery, and Claudio’s—a restaurant that once operated as a Prohibition-era speakeasy. Beyond town, rows of grapevines cover hillsides at over 40 wineries open for tastings. The village’s mix of old docks and modern ferries shows how it adapts without losing its roots.
Shipbuilding History and Harbor Life
Greenport’s deep harbor made it a center for shipbuilding and oyster harvesting starting in the 1700s. The Long Island Rail Road reached the village in 1844, linking it to New York City and helping businesses grow. During the 1920s, fast boats smuggled alcohol into Claudio’s and other spots hidden behind waterfront warehouses. Today, the Greenport Village Historic District protects over 50 buildings from the 1800s, including Greek Revival houses and old general stores. Visit the East End Seaport Museum in September for their annual Maritime Festival, where you can tour vintage boats or watch blacksmiths demonstrate traditional metalwork.
Mitchell Park: Year-Round Gatherings
Mitchell Park’s grassy area faces the harbor, where sailboats dock during warmer months. A 1920s carousel with hand-carved horses operates daily in summer and weekends from October to April, playing music from its original band organ. From December to February, the park floods part of its lawn to create an ice rink with views of the water. Skateboarders use the concrete ramps and rails at the Moore’s Lane skate park, built in 2018. Summer evenings bring food trucks serving lobster rolls to picnic tables, and local bands play under the pavilion’s string lights.
Seasonal Highlights: Beaches, Farms, and Festivals
In April and May, cherry trees bloom along Main Street, and cyclists ride past wineries on flat roads lined with daffodils. July and August draw swimmers to Town Beach’s sandy stretch or Goldsmith Inlet’s rocky tide pools, while fishing charters leave at dawn for striped bass. By October, farms east of Greenport host pumpkin patches and apple cider tastings, and wineries hold grape-stomping contests. Winter brings weekend holiday markets selling handmade ornaments, and the Greenport Brewing Company serves spiced ale beside fire pits.
Restaurants and Local Food
Eat wood-fired pizza at La Capricciosa Pizza, known for thin crusts topped with locally grown zucchini and clams. Claudio’s deck serves raw oysters from Peconic Bay alongside steamed lobsters, with tables overlooking incoming ferries. Many menus list dishes like fluke crudo or scallops seared in rosemary butter, often paired with nearby vineyards’ chardonnay. Stop at Lucharitos for soft-serve ice cream swirled with crushed strawberries, or try small-batch coffee roasted at Aldo’s.
Boating, Fishing, and Nearby Islands
Sign up for a two-hour cruise to Horton Point Lighthouse, where you can climb 52 steps to see Long Island Sound from the 1857 tower. Rent kayaks at Stirling Harbor Marina to paddle through Shelter Island’s calm coves, or take the North Ferry for a 10-minute ride to Shelter Island’s hiking trails. Fishing charters provide rods and bait for catching fluke near Plum Island, and sailing lessons teach how to hoist sails on classic sloops.
Getting Here and Getting Around
Take the Long Island Rail Road from Penn Station to Greenport’s 1844 train station, with a shuttle transfer at Ronkonkoma. If driving, follow Route 25 past farm stands selling sweet corn and hydrangeas. Walk everywhere once you arrive—sidewalks connect the harbor to shops and restaurants in under 15 minutes. Rent bikes at 4th Street Cycles to explore back roads leading to beaches. Stay at waterfront hotels like the Harbor House Inn or book a cottage with a porch facing the marina.
Houses and Neighborhoods
Greenport’s residential streets have Victorian farmhouses with wide porches and Cape Cod-style homes painted in gray or blue. The 1886 Sterling Avenue Victorian keeps its original stained glass and clawfoot tubs but adds heated bathroom floors. Smaller cottages near Sunset Lane, many built in the 1940s, sit a five-minute walk from Shellfisher Beach. Current real estate listings include renovated captains’ houses with boat docks and modern condos above boutique stores on Front Street.
