60 days in Long Island Itinerary

60 days in Long Island Itinerary

Created using Inspirock Long Island travel route maker

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Route & dates

60 days in Long Island Itinerary

Start: Newark
Drive:  3​h
1
Montauk
— 17 nights
Drive:  1​h 15​min
2
Riverhead
— 20 nights
Drive:  1​h 30​min
3
Freeport
— 22 nights
Drive:  1​h 15​min
End: Newark

17
nights
Montauk

Montauk ©
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. Do some cultural sightseeing at Montauk Point Lighthouse and Main Beach. Get in touch with nature at Fishing Charters & Tours and Orient Beach State Park. Venture out of the city with trips to Sag Harbor (Havens Beach, Sag Harbor Marine Park, & more), Orient (Oysterponds Historical Society, The Candy Man, & more) and East Hampton (Round Swamp Farm, Cedar Point County Park, & more). There's still lots to do: tour the pleasant surroundings at Ditch Plains, admire the majestic nature at Montauk Point State Park, steep yourself in history at Camp Hero State Park, and enjoy the sand and surf at Gin Beach.

To see photos, more things to do, ratings, and more tourist information, read Montauk trip itinerary builder .

Newark to Montauk is an approximately 3-hour car ride. While traveling from Newark, expect little chillier days and about the same nights in Montauk, ranging from highs of 65°F to lows of 50°F. On the 18th (Sat), you'll travel to Riverhead.

Things to do in Montauk

Parks Outdoors Beaches

Side Trips

East Hampton, Sag Harbor, Orient, Sagaponack, Bridgehampton
Highlights from your plan
Montauk Point Lighthouse ©
Montauk Point Lighthouse
Fishing Charters & Tours
Orient Beach State Park ©
Orient Beach State Park

20
nights
Riverhead

Riverhead ©
Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. Visiting Cooper's Beach and Fire Island National Seashore will get you outdoors. Do some cultural sightseeing at Alex Ferrone Gallery and Long Island Maritime Museum. Venture out of the city with trips to Mashomack Preserve (in Shelter Island), Bayard Cutting Arboretum (in Great River) and Pugliese Vineyards (in Cutchogue). And it doesn't end there: stroll through Ponquogue Beach, identify plant and animal life at Avalon Park & Preserve, revel in the low prices at Tanger Outlets, and take a peaceful walk through Wertheim National Wildlife Refuge.

To see more things to do, traveler tips, maps, and more tourist information, read Riverhead attractions planner.

Traveling by car from Montauk to Riverhead takes 1.5 hours. In May in Riverhead, expect temperatures between 66°F during the day and 46°F at night. Finish up your sightseeing early on the 7th (Fri) so you can travel to Freeport.

Things to do in Riverhead

Wineries Parks Wildlife

Side Trips

Cutchogue, Southold, Southampton, Peconic, Jamesport
Highlights from your plan
Sannino Bella Vita Vineyard ©
Sannino Bella Vita Vineyard
Bayard Cutting Arboretum ©
Bayard Cutting Arboretum
Mashomack Preserve ©
Mashomack Preserve

22
nights
Freeport

Freeport ©
Freeport is a village in the town of Hempstead, Nassau County, New York, USA, on the South Shore of Long Island. Popular historic sites such as Sands Point Preserve and Queens County Farm Museum are in your itinerary. Let the collections at Sagamore Hill National Historic Site and Nassau County Museum of Art capture your imagination. Explore the numerous day-trip ideas around Freeport: Glen Cove (Holocaust Memorial & Tolerance Center of Nassau County & Garvies Point Museum and Preserve), Great Neck Steppingstone Park (in Great Neck) and Sands-Willets House (in Port Washington). Pack the 20th (Thu) with family-friendly diversions at Adventureland. And it doesn't end there: stroll through Long Beach, kick back and relax at Lido Beach, identify plant and animal life at Norman J. Levy Park & Preserve, and buy something for everyone on your list at Roosevelt Field.

To find where to stay, maps, ratings, and tourist information, read Freeport trip planner .

You can drive from Riverhead to Freeport in 1.5 hours. Traveling from Riverhead in June, Freeport is somewhat warmer at night with lows of 62°F. Cap off your sightseeing on the 29th (Sat) early enough to go by car back home.

Things to do in Freeport

Parks Nature Museums

Side Trips

Huntington, Garden City, Roslyn, Farmingdale, Oyster Bay
Highlights from your plan
Jones Beach State Park ©
Jones Beach State Park
Sagamore Hill National Historic Site ©
Sands Point Preserve ©
Sands Point Preserve

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