Explore Two Long Island Villages With Winter Charm

Winter’s simplistic beauty stretches all across Long Island. From the grace of a chilly sunset to the serenity of a barren shorefront, it’s easy to marvel at the charm. After spending time outdoors, a cozy restaurant with good food and company are the perfect way to end the day. Montauk and Freeport are two Long Island villages where both indoor and outdoor enjoyment come easy.

Related Content: Explore Two Quaint Long Island Towns



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Montauk Point State Park

A popular summer destination, Montauk Point State Park is equally captivating during the off-season. Open from sunrise to sunset, visitors can experience gorgeous views of where the Atlantic Ocean meets the Block Island Sound. Another bonus: a walk along the rocky shoreline in view of the Montauk Lighthouse is free of crowds and perfect for photos. The trails within the park can also be used for hiking and watching seals take in some sun on the rocks offshore—just make sure to bundle up. Phone: 631-668-3781 | Address: 2000 Old Montauk Hwy Click to go

Shadmoor State Park

Lauded for its hiking trails and breathtaking beachside bluff, Shadmoor State Park has winter day trip written all over it. On a day clear of snowfall, pile into the car, bring a camera and head East. Phone: 631-668-3781 | Address: 900 Montauk Highway Click to go

Shagwong Tavern

A Montauk Highway mainstay, the Shagwong sure knows how to make its guests feel comfortable. The tables are cozy, intimate and built for good conversation. And the menu tugs at the heartstrings with delicious comfort fare like fried calamari, ravioli with roasted tomato pesto and burgers with crispy bacon or caramelized onions. Phone: 631-668-3050 | Address: 774 Montauk Hwy Click to go



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Captain Lou Fleet

Partake in a two-hour cruise aboard the Captain Lou Fleet to catch a glimpse of winter harbor seals. There is always a naturalist onboard to discuss biology and behavior of seals and other marine life encountered. Those allergic to the cold listen up: there’s also a heated cabin and warm beverages available. Phone: 516-623-5823 | Address: 28A Woodcleft Ave Click to go

Pier 95 Restaurant

Even in the winter, panoramic water views of the Hudson Canal never lose their beauty. The dining room is warm, romantic and has all the trappings of the perfect cozy evening—starting with the food. Choosing from a Mediterranean menu with Portuguese influences, diners can’t go wrong with any of the seafood selections. Delight the palate with stuffed shrimp, seafood linguini or paellas. Phone: 516-578-2700 | Address: 95 Hudson Ave Click to go

Raimo’s Restaurant and Pizzeria

Nothing says comfort like Italian food. And Raimo’s has the recipes for success. After a day outdoors (or not!) warm up with a slice of the famed Sicilian pizza where the cheese is melted to perfection. Any of the pasta entrees are also known to hit the spot. Phone: 516-378-4379 | Address: 187 W Merrick Rd Click to go