Greenport's hidden gems blend history, oysters and coastal charm

Stargaze at an observatory, tour a fireboat museum, or shuck oysters by the bay. This Long Island village packs surprises at every turn. Greenport's blend of old-world charm and seaside energy makes it an unforgettable retreat.

, and Administrator

2026 May 17 . 2:02 PM

1 min read

The image shows a poster with a map of Long Island, New York, with the words "Buy Homes on Long... — The image shows a poster with a map of Long Island, New York, with the words "Buy Homes on Long Island" written across the top. The map is detailed and shows the various cities and towns along the island, as well as the various bodies of water that make up the island. The colors used on the map are mostly shades of blue and green, with some yellow and red accents. The text is written in a bold font and is surrounded by a white border.

Greenport's hidden gems blend history, oysters and coastal charm

Greenport, a historic harbour village at the eastern tip of Long Island’s North Fork, offers visitors a mix of charm and activity. Just a few hours’ drive from the city, it blends a well-preserved historic district with lively waterfront dining and unique attractions. From stargazing to oyster shucking, the village provides plenty to explore. One of the standout spots is the Custer Institute and Observatory, open every Saturday night for public stargazing. Nearby, the Fireboat Firefighter Museum gives visitors a chance to step aboard a retired FDNY fireboat, now a floating museum.

For history lovers, Brecknock Hall—a grand 1857 mansion—offers tours when no weddings are scheduled. Those seeking relaxation can stay at Harbor Knoll Bed and Breakfast, where cozy rooms come with spectacular harbour views. Food and drink options abound, including Southold Bay Oysters, which provides tours and oyster-shucking lessons. Wine enthusiasts can visit Kontokosta Winery, where tastings come with sweeping ocean views. Just outside Greenport, Lavender by the Bay in East Marion invites guests to wander through fragrant, family-run lavender fields.

Greenport’s mix of historic sites, waterfront activities, and local flavours makes it a standout destination. Visitors can tour a 19th-century mansion, sample fresh oysters, or simply enjoy the harbour breeze. The village’s blend of culture and coastal charm ensures a memorable trip.