Directions from Manhattan, 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.


Bass Ridge Golf Course

Golf Courses – Hinsdale, Massachusetts

Bill Basilier's commitment to the course has enabled Bas Ridge to develop a reputation as a fine course in only 5 short years. More on GolfReview

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  • The views are nice, as you can see for miles around. More on golflink.com

  • Hidden Gem I hate to tell the world about this place, however it deserves it. I've played lots of fancy courses, but this one remains my favorite. It's not fancy. It's just fun. It has several chal... More on golflink.com

T and R Marina Inc

Things To Do – Piermont, New York

There are friendly people there and it is within walking distance to many fine restaurants in the Village of Piermont. More on CitySearch

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  • This is a small marina in Piermont, New York which has alot of charm. There are friendly people there and it is within walking ... More on CitySearch

Diane's Books

My family and I have been going to Diane's (yes, this really is independently owned by a real person named Diane) for more than twenty years. She and her wonderful staff have shaped, nurtured, and sup ... More on TripAdvisor

Haagen-Dazs Shop

Ice Cream – Greenwich, Connecticut

Lake Waramaug Country Club

Golf Courses – New Preston Marble Dale, Connecticut

One of the oldest golf courses in Connecticut, LWCC is a private 9 hole course first opened in 1898 as a 4 hole ... More on GolfReview

Red Carpet Inn

Things To Do – New Baltimore, New York

Motel located right off NYS Thruway exit 21B. Also a truck stop. More on iloveny.com

The Purdy Burying Ground

Landmarks – Rye, New York

Inscription. Pre-Revolutionary place of interment of one of Rye's early families. This tract of land was purchased by Joseph Purdy from John Budd in 1685. , Location. 40° 57.964′ N, 73° 41.248′ W. Marker is in ... More on HMDB

Old Rhinebeck Aerodrome Museum

Museums – Rhinebeck, New York

As a pilot this is one of my favorite reasons for living in the area. Check their website for all the detai... More on TripAdvisor

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  • My husband and I enjoyed our day at the aerodome. The museum,planes and show was excellent. Everyone includ... More on TripAdvisor

  • Antique airplane museum featuring WWI and barnstorming era airplanes on display and in thrilling air shows... More on Dutchesstourism.com

Fun Zone Of Bruckner Shp Plz

Themeparks – Armonk, New York

Category: Amusement Places Fun Zone Of Bruckner Shp Plz is a top source of entertainment in New York. Visit us at our location ... More on localamusementparks.com

Tonetta Lake

Lakes – Brewster, New York

'Tonetta Lake' (also known as Lake Tonetta) is a freshwater lake located in the Town of Southeast (Brewster), NY. Lake Tonetta has the only public beach in Southeast, accessible to town residents and their guests. In addition to ... More on Wikipedia

Pawling House Bed & Breakfast

Things To Do – Pawling, New York

Four rooms in a lovely 1860's house, fully renovated, private bath, full breakfast, a/c, coffee bar, wi-fi, Jacuzzi in master ... More on iloveny.com

Chicken Joe's

Restaurants – Cos Cob, Connecticut

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Annie's Cafe

Restaurants – Harrison, New York

Slice of New York Pizzeria

Restaurants – Stanfordville, New York