Directions from Boston, 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.


Point (The)

Things To Do – Bolton, New York

Cottages with fireplaces, on Lake George; Bolton Landing area. Boats, docks, wi-fi. More on iloveny.com

Nostalgia Pub

Bars – Southbridge, Massachusetts

Nostalgia Pub - Think of Nostalgia Pub as a guaranteed hangover. And we mean that in the best possible way. Located at 213 Mechanic St, it’s open all night, so it’s a pretty good bet that you’re going to be ... More on clubzone

North Warren Trailblazers

Things To Do – Chestertown, New York

Trails in northwestern Warren County. One of 4 area snowmobile clubs. ATV's are NOT allowed on snowmobile ... More on iloveny.com

Roger's Island Visitors Center

Things To Do – Fort Edward, New York

The island served as a base camp for the famous fighter Maj. Robert Rogers and his Rangers during the French and Indian War. From 1756 to 1759, Rogers Island was used as a training ground for Major... More on Heritage

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  • Inscription. Barracks  Hospital, Brick – kiln, 1755, , Erected by State of New York. , Location. 43° 15.831′ N, 73° 35.07′ W. Marker is in Fort Edward, New York, in Was... More on HMDB

The Riverway

Parks – Shrewsbury, Massachusetts

The Riverway and Olmsted Park form a green space that runs through Boston and a portion of Brookline linking the Boston Common and Franklin Park. Th e Riverway forms the lower, narrower section of the Emerald Necklace Park System ... More on KidsPlayParks

McCormack's Cottages

Things To Do – Indian Lake, New York

2 cozy lakeside cottages just south of Indian Lake, with a private sand beach. More on iloveny.com

We haven't found one that we love yet...

Parks – Watervliet, New York

We will be removing our current outdated playground and replacing it with a newer bigger and SAFER play area. More on KaBoom.org

Lablanc Glen

Things To Do – Garnet Lake, New York

Half-Nelson Playground

Parks – Ticonderoga, New York

E & R Sport Fishing Charters

Things To Do – Bolton, New York

Lake trout, landlocked salmon and bass fishing on Lake George, all bait and tackle supplied. USCG Licensed Captain and New York ... More on iloveny.com

Marlorough Skatepark, Marlborough, MA Massachusetts

Parks – Hudson, Massachusetts

This place is OK.. all steel/metal w. E it is, it has 4 qurter pipes, one 4 feet, all others 5 feet, a bank that has litterally no transition, stairs, the stairs are probably good for stalling... cant really jump them,, a rail, a ... More on skateboardpark.com

Lilac Park

Parks – Lenox, Massachusetts

Town picnic and rest area - Recently restored by the Lenox Garden Club to its original collection of ... More on Lenox.org

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  • Town picnic and rest area - Recently restored by the Lenox Garden Club to its original collection ... More on uptake_content

Honey Dew Donuts

Restaurants – Dudley, Massachusetts

Jims

Restaurants – Castleton-on-Hudson, New York

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Sobor Caribeno Restaurant

Restaurants – Albany, New York

Enjoy one complimentary LUNCH OR DINNER ENTREE when a second LUNCH OR DINNER ENTREE is purchased . . Serving delicious Spanish cuisine ... More on entertainment.com