Directions from Gloucester, Massachusetts to Highland, 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.


Dunkin' Donuts

Donuts – Wethersfield, Connecticut

Maverick Concerts

Things To Do – Woodstock, New York

Concerts feature world-renowned chamber music ensembles in a historic, woodland setting. Children's concerts on Saturdays. More on iloveny.com

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  • Maverick Concert Hall - Beer? Check. Newspapers? Check. Maverick Concert Hall, at Maverick Road, offers your usual selection of imports, domestics, and so on. Craaaaazy, out-of-control entertainmen... More on clubzone

Kelder's Farm

Things To Do – Kerhonkson, New York

Precut Christmas trees, Christmas wreaths and boughs, Santa appearances, Christmas decorations, trees bagged, prepicked produce, gift shop, snacks and refreshment stand, restrooms, picnic area, petting zoo . Our products are usually ... More on pickyourownchristmastree

Edmonston House 1755

Landmarks – New Windsor, New York

Restored 1755 stone house. Revolutionary period exhibits, blacksmith shop, slave quarters. Headquarters of the National Temple ... More on Orangetourism.org

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  • OverviewVisit this restored stone house with an interesting grounds, a blacksith shop and slave quarters.Property Information ... More on Travel.yahoo.com

Cedar Glen Golf Course

Golf Courses – Saugus, Massachusetts

relaxed public course atmosphere. More on golflink.com

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  • Maybe it's because it's early spring and they haven't had a chance to get out there and clean it up. More on golflink.com

  • Tee times not necessary at this course. Good course for players developing their skills. Blue tee boxes can present some challenging looks. ... More on golflink.com

A O H Division

Things To Do – Mountainville, New York

Broken Arrow Nursery

Entertainment Venue And Sports Arenas – Hamden, Connecticut

Choose and cut Christmas Trees More on pickyourownchristmastree

Lil Sue's Hideaway

Nightlife – Poughkeepsie, New York

Lil Sue's Hideaway - In need of a quick drink without the hassle of a doorman? Lil Sue's Hideaway will do the trick. Grab a seat at the welcoming bar and order one of the many brews on hand. The bartender will likely ... More on clubzone

J and R Gourmet Deli

Restaurants – Poughkeepsie, New York

J And R Gourmet Deli is located in New York. More on Open List

Good Cooking Ventures

Restaurants – Middletown, New York

Moe and Julies

Restaurants – Amenia, New York

Econo Lodge - West Point

Things To Do – Highlands, New York

54 rooms including kitchenettes and Jacuzzi suites near the U.S.M.A. at West Point. Pet friendly. More on iloveny.com

Candlewood Yacht Club

Things To Do – New Fairfield, Connecticut