Directions from Chatham, Massachusetts to Montgomery, 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.


Esopus Meadows

Landmarks – Staatsburg, New York

The highlight of the cruise for us was, of course, great views of the Rondout Lighthouse and the Esopus Meadows Lighthouse, but we also enjoyed other magnificent sites in a colorful fall setting. More on LighthouseFriends.com

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  • Alphonsus Seminary, a stately Gothic building. More on LighthouseFriends.com

  • We just happened to arrive in Kingston as a tour group was boarding the Rip Van Winkle for a cruise down the Hudson River. It wasn't a scheduled public cruise, but they gladly accepted our money an... More on LighthouseFriends.com

Poughkeepsie Riverfront

Themeparks – Poughkeepsie, New York

Poughkeepsie Riverfront, located at North Water Street, Waryas Park, has about what you’d expect from your corner deli: beer, soda, and some not-so-low-calorie snacks. Don’t come here expecting a night’s worth of entertainment, but ... More on clubzone

Riverfront Miniature Golf

Golf Courses – Farmington, Connecticut

The area's newest & most beautiful course situated on the banks of the Farmington river - Waterfalls, water hazards & fountains - Ice cream parlour featuring gourmet hard & soft ice cream - Special group ... More on entertainment.com

Manchester Historical Society

Museums – Manchester, Connecticut

Topics: historical societies. More on MuseumStuff.com

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  • In addition to programs and publications, the Manchester Historical Society co-sponsors a walking tour of the Cheney Brothers National Historic Landmark District. The society manages The History Ce... More on Heritage

Bruderhof Museum

Museums – Rifton, New York

The Bruderhof Museum brings to life the 80-year history of the Bruderhof,an international Christian communal movement. Designed by the youth, the museum houses a dozen ... More on MuseumStuff.com

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  • The Bruderhof Museum celebrates the 80-yr history of the Bruderhof communities. The museum includes multi-media displays and detailed historical ... More on iloveny.com

Barry Knight Guided Walks

Things To Do – West Hurley, New York

Easy hike to campsite, tower and views of the Catskill mountains, Ashokan Reservoir, Mohonk Mountain House and more. Receive ... More on iloveny.com

Mountain View Farm

Things To Do – Gardiner, New York

Horseback riding, lessons, and boarding. 12.2 miles of trails on the Wallkill Valley Rail Trail. Campers ... More on iloveny.com

East Mountain Golf Course

Golf Courses – Waterbury, Connecticut

The Pro Shop and snack bar staff were pleasant and accommodating . More on golflink.com

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  • The staff at the course was gracious and very knowledgeable . More on golflink.com

  • Nice but needs upkeep Nice wide fairways. Most greens are sloping. Mud on several holes. No water hazards. More on golflink.com

Prana Center

Health Club – Holliston, Massachusetts

Kripalu Yoga for adults, prenatal yoga, mom/baby yoga, as well as yoga for children and teens! Drop-ins welcome. More on YogaFinder

Pell Farms

Things To Do – Grafton, Massachusetts

Choose and cut your own Christmas trees, wreaths . Christmas tree varieties: U-Choose and Cut varieties: White Spruce More on pickyourownchristmastree

Dunkin' Donuts

Donuts – Bristol, Connecticut

Binh Duong Restaurant

Restaurants – Worcester, Massachusetts

2 Hopewell

Restaurants – South Glastonbury, Connecticut

One of the best restaurants I have ever visited. More on Yahoo! Travel

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  • The braised short ribs and gnocchi dish is AMAZING! More on Yahoo! Travel

  • One of the best restaurants I have ever visited. You really cannot go wrong with any item on the menu. The braised short ribs and gnocchi dish is AMAZING! The Atmosphere is very welcoming and the s... More on Yahoo! Travel

Hometown Pizza

Restaurants – Bristol, Connecticut

The Asa Waters Mansion

Museums – Millbury, Massachusetts

Asa Waters II was born in 1769 in the section of Sutton which later became Millbury in 1813. He learned the art of gunsmithing in his fatherâs shop. Because of lucrative government contracts, the armory, which he and his brother founded, ... More on MuseumsUSA.org