31 days in Long Island Itinerary

31 days in Long Island Itinerary

Created using Inspirock Long Island travel route builder

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Plan created by another user. Make it yours

Route & dates

1
Montauk
— 9 nights
2
Riverhead
— 10 nights
3
Freeport
— 11 nights

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. Second House Museum and The Leiber Collection will appeal to museum buffs. Get a sense of the local culture at Montauk Point Lighthouse and Oysterponds Historical Society. Explore the numerous day-trip ideas around Montauk: Wolffer Estate Vineyard (in Sagaponack), East Hampton (Round Swamp Farm & Home Sweet Home Museum) and Orient (Orient Beach State Park & The Candy Man). Next up on the itinerary: cast your line with a fishing tour, don't miss a visit to Gosman's Restaurant, kick back and relax at Gin Beach, and steep yourself in history at Camp Hero State Park.

For photos, maps, more things to do, and tourist information, read Montauk trip itinerary planning tool.

Newark to Montauk is an approximately 3-hour car ride. You can also take a train; or take a bus. When traveling from Newark in May, plan for little chillier days in Montauk, with highs around °F, while nights are about the same with lows around °F. Wrap up your sightseeing on the 10th (Fri) early enough to drive 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
Orient Beach State Park ©
Orient Beach State Park

10
nights
Riverhead

Riverhead ©
Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. Get some cultural insight at Alex Ferrone Gallery and William Floyd Estate. Visit Cooper's Beach and Cupsogue Beach County Park for some beach relaxation. You'll find plenty of places to visit near Riverhead: Fire Island National Seashore (in Patchogue), Setauket Neighborhood House (in Setauket) and Long Island Maritime Museum (in West Sayville). There's still lots to do: identify plant and animal life at Bayard Cutting Arboretum, do a tasting at Sannino Bella Vita Vineyard, admire nature's wide array of creatures at Long Island Aquarium, and get some fabulous bargains at Tanger Outlets Riverhead.

To see reviews, ratings, traveler tips, and other tourist information, read our Riverhead road trip planner.

Traveling by car from Montauk to Riverhead takes 1.5 hours. In May, plan for daily highs up to °F, and evening lows to °F. Wrap up your sightseeing on the 20th (Mon) to allow time to travel to Freeport.

Things to do in Riverhead

Parks Wineries Beaches

Side Trips

Peconic, Southampton, Cutchogue, Southold, Stony Brook
Highlights from your plan
Cooper's Beach ©
Cooper's Beach
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. For shopping fun, head to Tanger Outlets Deer Park or Book Revue. Visit Long Beach and Great Neck Steppingstone Park for some beach relaxation. Explore the numerous day-trip ideas around Freeport: Vanderbilt Museum and Planetarium (in Centerport), Sands Point Preserve (in Port Washington) and Oyster Bay (Sagamore Hill National Historic Site, 20th Century Cycles, &more). There's still lots to do: kick back and relax at Jones Beach State Park, immerse yourself in nature at Sunken Meadow State Park, admire the masterpieces at Nassau County Museum of Art, and browse the different shops at Roosevelt Field.

For other places to visit, traveler tips, more things to do, and more tourist information, use the Freeport trip itinerary builder site.

Drive from Riverhead to Freeport in 1.5 hours. Traveling from Riverhead in May, plan for somewhat warmer nights in Freeport, with lows around °F. Finish your sightseeing early on the 31st (Fri) to allow enough time to drive back home.

Things to do in Freeport

Museums Parks Historic Sites

Side Trips

Huntington, Garden City, Oyster Bay, Port Washington, Roslyn
Highlights from your plan
Sagamore Hill National Historic Site ©
Sagamore Hill National Historic Site
Sands Point Preserve ©
Sands Point Preserve
Cradle of Aviation Museum ©
Cradle of Aviation Museum

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