Directions from Boston, Massachusetts to Highland, 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.


Churchill Gardens

Gardens – Woodbury, Connecticut

Choose and cut Christmas Trees More on pickyourownchristmastree

Jones Point Path

Things To Do – Peekskill, New York

Still, it is a nice * marsh with good views of the mountains behind you. More on TrailLink.com

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  • Good views through the trees of the Hudson and Westchester hills. More on TrailLink.com

  • "As the posted trail description indicates, the Jones Point Path is a route bicyclists bound to and from the Bear Mountain Bridge can use to avoid a very dangerous segment of US Route 9W. The trail... More on TrailLink.com

Patterson Baptist Church Patterson 200 Years

Landmarks – Patterson, New York

Inscription. Patterson Baptist Church, (The Rock Church), 1790, The Baptist Church: The following material was adapted from notes put together by Reverend James B. M. Frost, March 1993: Pelletreaus “History of Putnam County, ... More on HMDB

Kaaterskill Clove

Parks – Palenville, New York

Includes Flight 98, Palenville Corner, Palenville Pillar, The Chasm, Jeff's Wet Dream, Moore's Bridge Area, Hillyer Falls, Viola Falls, Wildcat ... More on RockClimbing

Waterville Veterans

Landmarks – Waterbury, Connecticut

Inscription. Dedicated to, the men and women of, Waterville: who have served their country, in time of need, ——————, May this memorial stand, as a constant reminder of, their courage and patriotism, ... More on HMDB

Discovery Zone

Things To Do – Danbury, Connecticut

Sphinx Kaaban Shrine Club

Things To Do – Plymouth, Connecticut

Oxbow Pizza

3.0
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Joe's American Bar & Grill

Restaurants – Framingham, Massachusetts

The best value for you money. More on CitySearch

3.0
7 reviews
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4.5
1+ reviews
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  • great food great service! More on Yahoo! Travel

  • The best value for you money. The steak are out of this world and try the ribs too. More on CitySearch

Pueblitopaisa

Restaurants – Newburgh, New York

High Lonesome Rose Hurst Stable

Themeparks – Middlebury, Connecticut

Fun wooden trail rides for the family to ... More on Yahoo! Travel

Hyland Orchard Inc.

Farm – Fiskdale, Massachusetts

Fruit Orchard, PYO apples, pumpkins, picnic area, exotic animal attraction, micro brewery and tours, cider mill, sugar house, seasonal ice cream bar, farm bakery & retail ... More on allaboutapples.com