Directions from Nantucket, Massachusetts to Montauk, New York





UpTake Roadtrip Beta

We've selected a few points along the way for you to stop. We are trying to surface things you may not find elsewhere, but if we make some poor choices, please understand. Your feedback is appreciated.


Southold Historical Society

Museums – Southold, New York

The Southold Historical Society was founded in 1960 and chartered by New York State in 1965. We hold a large collection of original mansucripts, photographs, paintings and other obejects relating t... More on MuseumStuff.com

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  • Colonial and Victorian houses, schoolhouse, print shop, blacksmith shop, barn. Horton Point lighthouse ... More on iloveny.com

Barnstable Superior Courthouse

There's nothing "wrong" with the Courthouse. It's just that - well, it's a government center and there isn't very much in the ... More on TripAdvisor

Kavanaugh Park

Parks – Old Saybrook, Connecticut

Youth ballfield, playground, tennis, basketball courts and restroom. More on Oldsaybrookchamber.com

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  • Youth ballfield, playground, tennis, basketball courts and restroom. More on Oldsaybrookchamber.com

Avalon Lakefront Motel

Things To Do – Montauk, New York

Four acre unique country setting; BBQ, picnic area and fishing on freshwater lake; row and peddle boats. In-room coffee, refrigerators ... More on iloveny.com

Channing Daughter's Winery

Wineries And Vineyards – Bridgehampton, New York

While my brother was up visiting from Maryland, he thought it would be fun to hit up a winery. One of the closed places to where my parent’s ... More on igougo

Trustom Pond

Lakes – Charlestown, Rhode Island

'Trustom Pond' is a closed lagoon in South Kingstown, Washington County, Rhode Island, United States. It is one of nine coastal lagoons (referred to as "salt ponds" by locals) in southern Rhode Island. It has a surface area of , and ... More on Wikipedia

Out East Family Fun Center

Things To Do – Riverhead, New York

The Staff was polite and friendly . More on TripAdvisor

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  • The park was kept in spotless condition and we really did have a blast. More on TripAdvisor

  • We've done the whole Splish Splash thing before and didn't want to go that route again, so we decided to ch... More on TripAdvisor

Mystic River Marina, Mystic, CT

Things To Do – Mystic, Connecticut

On the west side of Mason's Island, located on the east shore of the Mystic River, is the Mystic River Marina. A family owned and operated business begun in 1957 by the late Eugene Garbarino and br... More on Mysticrivermarina.com

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  • Mystic River Marina is found on the secluded Mason's Island. A tranquil setting on the Mystic River with beautiful views of Long Island ... More on Mysticrivermarina.com

Black Cat Books

Book Shopping – Sag Harbor, New York

Fishers Island Ferry

Things To Do – New London, Connecticut

This is the connector ferry between New London, Connecticut and Fisher's Island, New York. Dogs of all sizes are allowed for no addition fee. ... More on DogFriendly.com

International Bakery

Restaurants – New Bedford, Massachusetts

3.5
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Panagakos Development

Restaurants – Seekonk, Massachusetts

Hercules Pizza Works

Restaurants – Lincoln, Rhode Island

Stonington Country Club

Golf Courses – Stonington, Connecticut

This club recently completed a renovation project, increasing to eighteen holes. The new holes were designed by Ron Forse. This course's fairways are narrow and lined with trees on the left. The gr... More on Golf.com

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  • The 18-hole "Stonington" course at the Stonington Country Club facility in Stonington, Connecticut features 6,510 yards of golf from the longest tees for a par of 72 . The course rating is 71.8 and... More on golflink.com