on Long Island

on Long Island

Charming Small Towns

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Long Island is home to amazing vineyards, fabulous restaurants, historic lighthouses, beautiful beaches, art galleries, museums, and lots of outdoor fun!

If you need a breather from city living, these Long Island towns are perfect! Here are my favorites.

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Greenport

This fishing village is one of the most walkable and best towns on Long Island. Browse the boutique shops, see the historical homes and museums, and take in the views of the marina. Don't forget to try the restaurants around!

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Oyster Bay

This town offers history and outdoor attractions such as Sagamore Hill, Teddy Roosevelt's former home, as well as Planting Fields Arboretum, a 409-acre estate around a Tudor Revival mansion!

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Shelter Island

Visit this hidden gem that's only a ferry from Greenport! Hike Mashomack Preserve, go kayaking, relax at the beautiful Shelter Island beaches, then try the unique restaurants around!

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Montauk

At the farthest end of Long Island, sits this romantic town. Check out farming boutiques and visit cafes and restaurants. Outdoor lovers can relax at the beaches and spend time at Montauk Point and Shadmoor state parks!

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Port Jefferson

This is rated as one of the best towns to live on Long Island, so it's a safe solo trip destination! The Downtown offers a theatre, boutiques, specialty coffee, and craft beer. For a true hidden gem experience, head to Pirate's Cove!

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Cutchogue

This hamlet is in the heart of Long Island’s wine country. So if you love win, this is the perfect place to visit! I recommend joining a biking tour that will take you to wineries and farms as well as visiting art spaces around!

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Click below for the full list of the loveliest Long Island Towns!

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