Directions from Plymouth, Massachusetts to Chestertown, 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.


Rogers Memorial Park

Parks – Bolton, New York

Swim, picnic. Late June-Labor Day. Parking fee. More on iloveny.com

Millay Poetry Trail at Steepletop

Parks – Austerlitz, New York

A ½ mile narrow country road for walking only is marked with a dozen favorite nature poems by Edna St. Vincent Millay. The trial ends at the final resting ground of ... More on iloveny.com

Gore Mountain

Things To Do – North Creek, New York

What I love best about Gore is the beautiful view of the Adirondack Mountains from the top.. More on SkiSite

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  • It is no frills (read: no lift lines, not crowded) with quick lifts, great views , and tons of good terrain. More on TripAdvisor

  • Laid back locals resort. Good terrain, very good snowmaking and grooming. Improvements around the base area resulting from the new Northwoods Lodge have really expanded the number of tables, seatin... More on SkiSite

Mt Knoll Beach Cottages

Things To Do – Bolton, New York

Directly on the lake, 2 bedroom cottages, living area, kitchen & bath. Private natural sandy beach. Peaceful, panoramic view of ... More on iloveny.com

Eleventh Mountain Farms & Vacation Houses

Things To Do – Bakers Mills, New York

Located in the Gore Mountain area. Close to skiing, whitewater rafting, hunting and fishing areas. More on iloveny.com

Oxford Tavern

Bars – Oxford, Massachusetts

Oxford Tavern - Beer, liquor and all other booze—it all ends up in the same place. If you’re looking for a decent fueling station ... More on clubzone

Canal Bowling Lanes

Bowling Alleys – Southampton, Massachusetts

Kids Birthday parties - Bumper bowling for kids - Adult, youth & senior leagues - Lounge & Keno - Corporate & private parties ... More on entertainment.com

General Stark

Landmarks – Schuylerville, New York

Inscription. General Stark, held this position to prevent, British retreat to north. , Erected 1927 by State of New York. , Location. 43° 7.102′ N, 73° 35.118′ W. Marker is near Schuylerville, New York, in Saratoga ... More on HMDB

Sacandaga Pathway

Parks – Speculator, New York

The Pathway is a 1-1/2 mile long boardwalk & path, which provides a unique opportunity by making wetlands, transitional forest, and upland timber areas accessible to all fitness levels. There are also several educational opportunities ... More on iloveny.com

Bearhurst Lakeside Cottages

Things To Do – Speculator, New York

5 guest cottages surround this lakeside Great camp, which dates from the early 1890's. Authentic Adirondack "Great Camp" architecture ... More on iloveny.com

Chesterwood Estate & Museum

Museums – Glendale, Massachusetts

New Dragon Garden Restaurant

Restaurants – Albany, New York

The food was excellent and they were very accommodating when I asked to customize a dish. More on Yahoo! Travel

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  • I order from here all the time and it is the best take out I have ever had. I highly recommend coming here. More on Restaurantica

  • The food was excellent and they were very accommodating when I asked to customize a dish. Although delivery... More on Yahoo! Travel

Alpine Grille

Restaurants – Northville, New York

Kettle Brook Golf Club

Golf Courses – Paxton, Massachusetts

All this for a very reasonable price -a rare gem. More on GolfReview

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  • Nice Public Course Definitely one of the better public golf courses in the area at any cost and possibly the best when you consider value . More on golflink.com

  • Nice Public Course Definitely one of the better public golf courses in the area at any cost and possibly the best when you consider value. With 5 sets of tees this course can play as long (6,912 ya... More on golflink.com