15 days in Long Island Itinerary

Created using Inspirock Long Island trip planner
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Make it your trip
Drive
1
Huntington
— 4 nights
Drive
2
Montauk
— 5 nights
Drive
3
Cutchogue
— 5 nights
Drive

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Huntington — 4 nights

The Town of Huntington is one of ten towns in Suffolk County, New York, United States. You'll explore the less-touristy side of things at Bethpage Black and Anthony's Nose. Explore Huntington's surroundings by going to Organics Today Farm (in East Islip), Bay Shore (Gardiner County Park & Sagtikos Manor) and Captree State Park (in Babylon). There's still lots to do: explore the world behind art at The Heckscher Museum of Art, look for all kinds of wild species at Teatown Lake Reservation, walk around Theodore Roosevelt Memorial Park, and stop by Book Revue.

To find ratings, where to stay, maps, and tourist information, you can read our Huntington online tour planner.

Newark to Huntington is an approximately 1.5-hour car ride. In October, daily temperatures in Huntington can reach 67°F, while at night they dip to 52°F. Finish your sightseeing early on the 12th (Tue) to allow enough time to drive to Montauk.
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Parks · Nature · Outdoors · Wildlife
Side Trips

Montauk — 5 nights

Montauk is a census-designated place (CDP) that includes the hamlet with the same name located in the town of East Hampton in Suffolk County, New York, on the eastern end of the South Shore of Long Island. Discover out-of-the-way places like Phantom Farms and Buffumville Lake. Venture out of the city with trips to Jaswell’s Farm (in Smithfield), Blackstone River and Canal Heritage State Park (in Uxbridge) and An Unlikely Story Bookstore (in Plainville). There's much more to do: take in the spiritual surroundings of St. Anne's Shrine, see the interesting displays at Optical Heritage Museum, tee off at Montauk Downs State Park Golf Course, and pause for some serene contemplation at St. Therese of Lisieux Catholic Church.

To see reviews, more things to do, and tourist information, you can read our Montauk day trip planner.

The Route module can help you plan travel from Huntington to Montauk. In October, daytime highs in Montauk are 65°F, while nighttime lows are 53°F. Finish your sightseeing early on the 17th (Sun) to allow enough time to drive to Cutchogue.
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Parks · Historic Sites · Nature · Museums
Side Trips

Cutchogue — 5 nights

Cutchogue is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. Discover out-of-the-way places like Sannino Bella Vita Vineyard and Pellegrini Vineyards. Change things up with these side-trips from Cutchogue: Massage Envy (in Rocky Point), Calverton (Calverton National Cemetery & Peconic River Herb Farm) and Shrine of Our Lady of the Island (in Manorville). There's much more to do: do a tasting at Coffee Pot Cellars Tasting Room, identify plant and animal life at Elizabeth A. Morton National Wildlife Refuge, relax in the rural setting at The East End Mushroom Company, and steep yourself in history at Wickham's Fruit Farm.

Make your Cutchogue itinerary with Inspirock to find out what to see and where to go.

Drive from Montauk to Cutchogue in 1.5 hours. In October in Cutchogue, expect temperatures between 64°F during the day and 52°F at night. Finish your sightseeing early on the 22nd (Fri) so you can drive back home.
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Wineries · Historic Sites · Parks · Shopping
Side Trips

Long Island travel guide

4.4
Wineries & Vineyards · Beaches · Lighthouses
Stretching northeast from New York Harbor to the Atlantic Ocean, Long Island is the largest island in the continental U.S. It technically includes the New York City boroughs of Brooklyn and Queens, but generally refers to the suburban counties of Nassau and Suffolk exclusively. Known for its cookie-cutter suburban neighborhoods, the island is also home to a wealth of intriguing places to visit, including beaches, scenic countryside, wineries, and numerous historical sites. In the summer months, wealthy New Yorkers flock here to relax in their exclusive Hamptons properties.
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