Directions from Montauk, New York to Lenox, Massachusetts





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.


Hamptons Drive-In

Things To Do – Bridgehampton, New York

Screens: 1 Sound: Car Capacity: Typical season: Technical details: none Hamptons Drive-In Timeline: 1976 - screen destroyed ... More on drive-ins.com

Squire's Tavern

Landmarks – Barkhamsted, Connecticut

Inscription. [ panel 1 ], Welcome to Squire's Tavern, Home to the Barkhamsted Historical Society, and the Farmington River Coordinating Committee, The Barkhamsted Historical Society, Squire's Tavern, like the nearby river, has a story ... More on HMDB

Tiana Beach

Things To Do – Hampton Bays, New York

1,000 feet Ocean Beach, nonresident fee More on Discoverlongisland.com

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  • 1,000 feet Ocean Beach, nonresident fee More on Discoverlongisland.com

York Lake

National And State Parks – New Marlborough, Massachusetts

This shallow, 40 acre, two story trout pond has a maximum depth of 16 feet and an average depth of 6 feet. Transparency is poor, extending to only 4 feet. The bottom is composed primarily of muck, and aquatic vegetation is abundant ... More on AnglerWeb.com

Civil War Parrott Rifle

Landmarks – Watervliet, New York

Inscription. 10 Pounder Rifle, From Watervliet Arsenal Designed, By Robert P. Parrott and Cast at, The West Point Foundry. Used by the Union Forces These, Guns were Mounted on Carriages, Made at Watervliet Arsenal Where, Ammunition ... More on HMDB

Albany Aqua Ducks & Trolleys

Things To Do – Albany, New York

I absolutelly love the Aqua Ducks. More on Trekaroo

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  • I absolutelly love the Aqua Ducks. As an educator this is one of my favorite things to do with my ... More on Trekaroo

  • Upstate New York's only amphibious tours take you through the historic streets of New York's Capital City ... More on Albany.org

Gristina Vineyards

Wineries And Vineyards – Cutchogue, New York

We all like tom, Tilli and marthann. They work hard. They always make us feel at home. Very friendly and ar... More on Yahoo! Travel

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  • A high profile and critically acclaimed vineyard that blends an intimate farmhouse tasting room setting wit... More on Travel.yahoo.com

Indian & Colonial Research Center

Museums – Old Mystic, Connecticut

USS Slater DE766

Museums – Albany, New York

After a 10-year restoration, the last remaining World War II Destroyer Escort, once a part of a fleet of more than 500 ships, now rests on the Hudson River at ... More on Moon Handbooks: New York

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  • The Museum is an educational and charitable Organization, organized under the laws of the State of New York, whose goal is to increase the general public's knowledge of our naval history and herita... More on MuseumStuff.com

Windsor True Value Hardware

Home and Garden Stores – Windsor, Connecticut

Peconic Bay Diner

Restaurants – Riverhead, New York

Food is good, kids love it. More on TripAdvisor

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  • Only 24 hour establishment in Riverhead where you can sit down and order a meal. Usual Diner food. Service ... More on TripAdvisor

  • I went there for lunch and asked for a table with an outlet so I could charge my notebook and get a little ... More on TripAdvisor

Subway Restaurant

Restaurants – Albany, New York

Subway's health-conscious menu is built around greaseless deli sandwiches--turkey, chicken, roast beef, etc.--made on soft rolls baked daily ... More on CitySearch

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  • Subway is located in New York. It's known for its deli. The menu is built around greaseless deli sandwiches. ... More on Open List

Sunwater's Grill Incorporated

Restaurants – Hampton Bays, New York

Best seafood in the Hamptons--Great location--Good value More on Yahoo! Travel

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  • Best seafood in the Hamptons -- Great location -- Good value More on Yahoo! Travel

Addison Park

Parks – Glastonbury, Connecticut

Addison Park is a kid friendly park located in Glastonbury CT. More on KidsPlayParks