Historic seaside charm meets modern tourism in Greenport.

Traces of the past dot the landscape of this historic seaport and fishing village, from plaques marking significant historical sites to old buildings that once housed tradesman and schoolchildren. The housing market in Greenport is a mix of well-kept single-family homes, a scattering of apartments, and few condos. Many of the buildings boast pristine Victorian facades, a nod to the community’s dedication to preserving the area’s distinct charm. People flock to the village for its tight-knit community and laid-back vibe.

There’s plenty of dining and entertainment options in this corner of Long Island. Farm stands and markets share the space with wineries and boutiques. Farm to table restaurants and hole-in-the-wall diners offer fresh seafood and other tasty fares. Greenport commands a thriving tourism industry, with hotspots like crowded fishing harbors and lush vineyards drawing heavy foot traffic during the summer months. A beloved 1920’s carousel hugs the waterfront, while cultural institutions like the East End Seaport Museum & Marine Foundation give guests a look at the region’s maritime history. The close-knit community enjoys a string of annual festivals and events like the famed Maritime Festival.

Nature is abundant in Greenport. Great blue herons, osprey, and other fowl are fixtures in the area. Nearby recreation areas boast playgrounds, grill-clad picnic pavilions, and hiking trails. Favorite pursuits in the region include kayaking, swimming, camping, fishing, boating, and paddle boarding. Orient Beach State Park is an ideal spot to marvel at local wildlife and wade along stretches of beach lined with pebbles.

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