Directions from Boston, Massachusetts to Poughkeepsie, 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.


Millers River Trail

Things To Do – Worcester, Massachusetts

The next time you want to ride some very single track and want some peace and tranquility to go with it try this trail. More on trails.mtbr.com

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  • This trail isn't used much but it is well maintained. More on trails.mtbr.com

  • This trail isn't used much but it is well maintained. Grate single track, very remote,a real sence of wilderness. It's you the railroad tracks and the river. The river is real nice, The beaver are ... More on trails.mtbr.com

Sherman Historical Society & Museum

Museums – Sherman, Connecticut

The society, founded in 1975, includes the Northrop House Museum, which was donated to the society in 1981 and is decorated with local furnishings mostly from the Mallory collection. The house was ... More on Heritage

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  • Sherman Historical Society, Dedicated to the preservation of the history of Sherman, Connecticut More on Shermanhistoricalsociety.org

West Point Tours, Inc.

Things To Do – West Point, New York

There are some breathtaking views of the Hudson River Valley on the way (and winding, narrow road with ... More on TripAdvisor

3.0
10 reviews
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  • Other than that, the hotel was fine. More on TripAdvisor

  • My sister and I came up with our parents at the end of April for my father's class reunion at West Point (t... More on TripAdvisor

Bob Feller Museum

Museums – Worcester, Massachusetts

Wide range of memorabilia from Feller's Hall of Fame baseball career with Cleveland Indians. Old uniforms, photographs, trophies, special awards and artwork. Specially ... More on TravelIowa.com

Lembo Lake Park - ATV NY

Parks – Modena, New York

ATV-NY at Lembo Lake Park is a legal riding facility for ATV's and motorcycles. Camping and fishing on site. More on iloveny.com

Drive-In

Things To Do – Bloomington, New York

Screens: 1 Sound: Car Capacity: 500 Typical season: Technical details: none Drive-In Timeline: There are no timeline ... More on drive-ins.com

Chippanee Golf Club

Golf Courses – Bristol, Connecticut

Chippanee Golf Club is an 18-hole regulation length golf course in Bristol, Connecticut. This short layout has 3 sets of teeboxes for a fun, but challenging golfing experience. Online tee times may... More on TheGolfCourses.net

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  • This is an old fashioned course with small, challenging greens, rolling terrain and very little water in play. A pond must be carried off the tee on hole #11, ... More on Golf.com

Maybrook Lodge - Kerhonkson

Parks – Kerhonkson, New York

Located in the Catskills, the Maybrook Lodge has hiking trails and a picnic area. More on iloveny.com

Battery Sherburne

Landmarks – West Point, New York

Inscription. occupied this site during, the Revolution, Built 1778, , Location. 41° 23.676′ N, 73° 57.471′ W. Marker is in West Point, New York, in Orange County. Marker is on Washington Road, on the right when ... More on HMDB

Noodle Noggin' 'N Bean

Things To Do – Northborough, Massachusetts

It looks deceiving from the outside, as it's located in an office building, but the inside is quite good.?� There ... More on Trekaroo

4.0
1 review
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4.0
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Maple Tree Gallery

Museums – Pawling, New York

Venice Restaurant

Restaurants – Ridgefield, Connecticut

I love this restaurant! More on Yahoo! Travel

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  • Whether enjoying an exquisite formal dinner or just a quick slice the food is aways great and the service even better. More on Yahoo! Travel

  • I love this restaurant! It has always been good but now under new management it's exceptional. I dine here at least once a week. Whether enjoying an exquisite formal dinner or ... More on Yahoo! Travel

Seasoned Kitchen

Restaurants – Roxbury, Connecticut

Mercato

Restaurants – Red Hook, New York

We were a party of four, two couples, and to make a long story short, we felt rushed throughout our 90 minu... More on TripAdvisor

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10 reviews
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  • Been here a number of times, and really want to say its great because I love the place the owner and the fa... More on TripAdvisor

  • Mercato is an Italian gem, the dining room’ s creamy walls full of everyday cheer. Francesco Buitoni,... More on travelandleisure

Sharon Country Club, Inc.

Golf Courses – Sharon, Connecticut

Sharon Country Club, Inc. is a 9-hole regulation length golf course in Sharon, Connecticut. This short layout will reward good shots and provide a fun golf outing for everyone. Online tee times may... More on TheGolfCourses.net

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  • The 9-hole "Sharon" course at the Sharon Country Club, Inc. facility in Sharon, Connecticut features 3,135 yards of golf from the longest tees for a par of 36 . The course rating ... More on golflink.com