Directions from New York, New York to Sheffield, 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.


Harvest Market on the Sound

Food Shopping – Mamaroneck, New York

Enjoy $20 off a minimum purchase of $100 or more . . Bringing Manhattan to Mamaroneck, leaving prices & the attitude behind - Your one stop shop catering to all your needs & more - Outstanding gourmet organic market including a full ... More on entertainment.com

Berkshire Fringe

Things To Do – Great Barrington, Massachusetts

Dynamic new works of theatre & dance by emerging artists from across the US & right here in the Berkshires. Tix ... More on Berkshires.org

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  • Dynamic new works of theatre & dance by emerging artists from across the US & right here in the Berkshires. ... More on uptake_content

Bruce Museum

Museums – Greenwich, Connecticut

I've been going to this museum since I was a little kid. More on Judysbook.com

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  • The Bruce Museum is a great resource in Southern Ct. More on Judysbook.com

  • The Bruce Museum is a great resource in Southern Ct. It is just the right size for a visit during wh... More on Judysbook.com

Blandford Ski Area

Ski Resorts – Huntington, Massachusetts

This place is also, despite how small it is, very well maintained, with lessons, games and everything. More on SkiTown.com

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  • The deals are great for skiing and food, and the food is excellent ! More on SkiTown.com

  • This place is very small, only about 450', yet it's one of my favorite ski mountains I've ever visited! The snow quality is outstanding. The crowding is decent at at least one chairlift, and the mo... More on SkiTown.com

Les Trois Emme Winery and Vineyard

Wineries And Vineyards – New Marlborough, Massachusetts

This family owned/run winery also treats their guests with hand crafted hors d'oeurves paired with its compliment in wine. All friendly dogs are allowed around the grounds, and the little ones that can be carried ... More on DogFriendly.com

Buena Vista Pride Park

Parks – Yonkers, New York

Wing's Castle

Things To Do – Millbrook, New York

These area's I was told are usually off limits to the public for safety sake as it is a good fall from any ... More on TripAdvisor

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  • I wouldn't recommend this attraction at the price of $10. More on TripAdvisor

  • Went away for a night to Wing’s Castle, and it was amazing. If you are looking for four square walls and a ... More on TripAdvisor

Torrington Skatepark, Torrington Connecticut

Themeparks – Torrington, Connecticut

Made only of metal. Has a speedramp, 4 and 6-foot drop-in, bowl corner (4 feet), rail about 12 feet long that is high and gradually lowers, fun-box, six-set of stairs. It also has a picnic ... More on skateboardpark.com

Sands Point

Landmarks – Sands Point, New York

Sands Point is not named for its sandy beaches but rather for its early owners. Brothers James, Samuel, and John Sands purchased 500 acres at the tip of Long Island's Cow Neck Peninsula in 1695. Sands Point Lighthouse is the third ... More on LighthouseFriends.com

Old Erie Path

Things To Do – Sparkill, New York

Also avail yourself of the many restaurants and shops in the picturesque village of Piermont. More on TrailLink.com

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  • The foliage is light then, which permits you to easily view the Hudson River and Westchester County, NY. More on TrailLink.com

  • "This is one of the best biking trails near NYC. I bike here at least 2 times per month and I never tire of the scenery. The best seasons to bike on this trail are late fall, winter and early sprin... More on TrailLink.com

Domino's Pizza

Restaurants – New Rochelle, New York

Olympic Pizza

Restaurants – Torrington, Connecticut

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