31 days in Long Island Itinerary

31 days in Long Island Itinerary

Created using Inspirock Long Island travel route builder

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Route & dates

31 days in Long Island Itinerary

Start: Newark
Drive:  3​h
1
Montauk
— 9 nights
Drive:  1​h 15​min
2
Riverhead
— 10 nights
Drive:  1​h 30​min
3
Freeport
— 11 nights
Drive:  1​h 15​min
End: Newark

9
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. Your itinerary includes some good beach time at Main Beach and Amsterdam Beach Preserve. Montauk Point Lighthouse and St. Therese of Lisieux Catholic Church will appeal to history buffs. Explore the numerous day-trip ideas around Montauk: Orient (Orient Beach State Park, The Candy Man, & more), East Hampton (Round Swamp Farm, Home Sweet Home Museum, & more) and Wolffer Estate Vineyard (in Sagaponack). And it doesn't end there: take a memorable tour with Tours, admire the majestic nature at Hither Hills State Park, contemplate in the serene atmosphere at First Presbyterian/Old Whaler's Church, and explore and take pictures at Camp Hero State Park.

For ratings, reviews, other places to visit, and tourist information, you can read our Montauk online tour planner .

Newark to Montauk is an approximately 3-hour car ride. Expect little chillier weather when traveling from Newark in May: highs in Montauk hover around 65°F, while lows dip to 50°F. Finish up your sightseeing early on the 10th (Fri) so you can go by car to Riverhead.

Things to do in Montauk

Parks Outdoors Beaches

Side Trips

East Hampton, Sag Harbor, Orient, Bridgehampton, Wolffer Estate Vineyard
Highlights from your plan
Montauk Point Lighthouse ©
Montauk Point Lighthouse
Fishing Charters & Tours
Oysterponds Historical Society ©
Oysterponds Historical Society

10
nights
Riverhead

Riverhead ©
Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. Your itinerary includes some good beach time at Cooper's Beach and Fire Island National Seashore. Get in touch with nature at Ponquogue Beach and Mashomack Preserve. You'll find plenty of places to visit near Riverhead: Setauket Neighborhood House (in Setauket), St. James General Store (in Saint James) and Long Island Maritime Museum (in West Sayville). The adventure continues: view the masterpieces at Alex Ferrone Gallery, contemplate the long history of William Floyd Estate, revel in the low prices at Tanger Outlets, and learn about winemaking at Sparkling Pointe.

For ratings, where to stay, and more tourist information, read our Riverhead visit planning tool .

Traveling by car from Montauk to Riverhead takes 1.5 hours. Expect a daytime high around 66°F in May, and nighttime lows around 46°F. Finish your sightseeing early on the 20th (Mon) so you can travel to Freeport.

Things to do in Riverhead

Parks Wineries Beaches

Side Trips

Peconic, Cutchogue, Southold, Southampton, Patchogue
Highlights from your plan
Fire Island National Seashore ©
Fire Island National Seashore
Bayard Cutting Arboretum ©
Bayard Cutting Arboretum
Mashomack Preserve ©
Mashomack Preserve

11
nights
Freeport

Freeport ©
Freeport is a village in the town of Hempstead, Nassau County, New York, USA, on the South Shore of Long Island. Head to Book Revue and Roosevelt Fieldfor some retail therapy. Get a sense of the local culture at Sands Point Preserve and Walt Whitman Birthplace. Get out of town with these interesting Freeport side-trips: Oyster Bay (Sagamore Hill National Historic Site, 20th Century Cycles, & more), Sands-Willets House (in Port Washington) and Vanderbilt Museum and Planetarium (in Centerport). There's much more to do: tour the pleasant surroundings at Long Beach, take in the architecture and atmosphere at Cathedral of the Incarnation, contemplate the long history of Queens County Farm Museum, and immerse yourself in nature at Caumsett State Park.

To find out how to plan a trip to Freeport, use our trip itinerary maker.

Drive from Riverhead to Freeport in 1.5 hours. Expect somewhat warmer evenings in Freeport when traveling from Riverhead in May, with lows around 52°F. Wrap up your sightseeing on the 31st (Fri) early enough to drive back home.

Things to do in Freeport

Museums Parks Historic Sites

Side Trips

Huntington, Garden City, Oyster Bay, Glen Cove, Old Bethpage
Highlights from your plan
Sagamore Hill National Historic Site ©
Sands Point Preserve ©
Sands Point Preserve
Cradle of Aviation Museum ©
Cradle of Aviation Museum

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