44 days in Long Island Itinerary

44 days in Long Island Itinerary

Created using Inspirock Long Island trip itinerary planner

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Route & dates

44 days in Long Island Itinerary

Start: Newark
Drive:  3​h
1
Montauk
— 14 nights
Drive:  1​h 30​min
2
Cutchogue
— 15 nights
Drive:  1​h 30​min
3
Farmingdale
— 14 nights
Drive:  1​h 15​min
End: Newark

14
nights
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. You'll explore and learn at Guild Hall and Fireboat Firefighter Museum. Your cultural itinerary includes sights like St. Therese of Lisieux Catholic Church and The Leiber Collection. Get out of town with these interesting Montauk side-trips: Southold (Southold Bay Oysters, The Old Field Vineyards, & more), Greenport (Congregation Tifereth Israel, Railroad Museum of Long Island, & more) and Orient (Orient Beach State Park, Oysterponds Historical Society, & more). Next up on the itinerary: admire the majestic nature at Camp Hero State Park, take a stroll through Main Beach, sample the tasty concoctions at Montauk Brewing Company, and enjoy the sand and surf at Ditch Plains.

To find traveler tips, other places to visit, more things to do, and tourist information, read Montauk trip itinerary maker tool .

Newark to Montauk is an approximately 3-hour car ride. Traveling from Newark in June, expect nights in Montauk to be about the same, around 60°F, while days are little chillier, around 74°F. Finish your sightseeing early on the 28th (Fri) so you can drive to Cutchogue.

Things to do in Montauk

Parks Outdoors Beaches

Side Trips

Southold, East Hampton, Sag Harbor, Greenport, Orient
Highlights from your plan
Fishing Charters & Tours
Guild Hall ©
Guild Hall
The Leiber Collection ©
The Leiber Collection

15
nights
Cutchogue

Cutchogue ©
Cutchogue is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. Satisfy your inner culture vulture at Pellegrini Vineyards and Castello di Borghese / Hargrave Vineyard. Deepen your sense of the past at sights like Wickham's Fruit Farm and Our Lady of Poland Catholic Church. Step out of Cutchogue with an excursion to Madoo Conservancy in Sagaponack--about 30 minutes away. The adventure continues: view the masterpieces at Alex Ferrone Gallery, do a tasting at Waters Crest Winery, identify plant and animal life at Elizabeth A. Morton National Wildlife Refuge, and admire the masterpieces at Parrish Art Museum.

To find more things to do, photos, and more tourist information, use the Cutchogue sightseeing planner.

You can drive from Montauk to Cutchogue in 1.5 hours. Expect a daytime high around 73°F in June, and nighttime lows around 60°F. Finish your sightseeing early on the 13th (Sat) to allow enough time to travel to Farmingdale.

Things to do in Cutchogue

Wineries Parks Museums

Side Trips

Southampton, Bridgehampton, Peconic, Mattituck, Jamesport
Highlights from your plan
Alex Ferrone Gallery ©
Alex Ferrone Gallery
Parrish Art Museum ©
Parrish Art Museum
Sannino Bella Vita Vineyard ©
Sannino Bella Vita Vineyard

14
nights
Farmingdale

Farmingdale ©
The Incorporated Village of Farmingdale is an incorporated village on Long Island within the Town of Oyster Bay in Nassau County, New York, in the United States. You'll explore the less-touristy side of things at William Floyd Estate and Long Island Maritime Museum. Get outdoors at Wertheim National Wildlife Refuge and Bayard Cutting Arboretum. Venture out of the city with trips to Quogue Wildlife Refuge (in Quogue), Corey Beach (in Blue Point) and Hampton Bays (Church of St. Rosalie & Meschutt Beach). Next up on the itinerary: steep yourself in history at Sagamore Hill National Historic Site, see the interesting displays at Cradle of Aviation Museum, tour the pleasant surroundings at Jones Beach State Park, and explore the galleries of Queens County Farm Museum.

To find ratings, reviews, maps, and other tourist information, read our Farmingdale road trip planning site .

Drive from Cutchogue to Farmingdale in 1.5 hours. In July, daytime highs in Farmingdale are 83°F, while nighttime lows are 69°F. Finish up your sightseeing early on the 27th (Sat) so you can go by car back home.

Things to do in Farmingdale

Parks Wildlife Museums

Side Trips

Shirley, Garden City, Huntington, Stony Brook, Hampton Bays
Highlights from your plan
William Floyd Estate ©
William Floyd Estate
Sagamore Hill National Historic Site ©
Bayard Cutting Arboretum ©
Bayard Cutting Arboretum

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