Directions from Dennis Port, Massachusetts to Windham, 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.


Olana State Historic Site

National And State Parks – Hudson, New York

Home of Hudson River School painter Frederic Church offering programs and tours, a system of carriage drives, gardens and 250 acres with opportunities for ... More on iloveny.com

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  • Construction on the Victorian Estate began in 1870 and was completed in 1876. It was the home of landscape art ... More on PlanetWare

Girl Scouts of Eastern Massachusetts

Things To Do – Middleboro, Massachusetts

about Girl Scouts of Eastern Massachusetts: Girl Scouts of Eastern Massachusetts (GSEM) is one of the largest organizations in New England dedicated to serving girls and was officially established in 2008 through the merger of three ... More on GoCityKids

Wading River Golf Course

Golf Courses – Norton, Massachusetts

A 200 yard par 3 bordered on the left with a trailer park, and on the right by a broken down, rusted Plmouth Reliant. More on GolfReview

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  • Umm..... this is a golf course? My lawn is in better shape than the fairways, and most of the tee boxes were astro turf. Signature hole would have to the 17th. A 200 yard par 3 bordered on the left... More on GolfReview

  • This par 3 course has many trees that can affect your shots and eight water hazards. The fairways are wide, and the greens are large. This is a great location for beginners ... More on Golf.com

John Stones Inn

Nightlife – Ashland, Massachusetts

A fun atmosphere with a great staff. More on Yahoo! Travel

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  • The food is delicious ! More on Yahoo! Travel

  • The food is delicious! A fun atmosphere with a great staff. More on Yahoo! Travel

Catskill Mountains Historic New York

National And State Parks – Hannacroix, New York

Inscription. The deep ravines, irregular ridges and rocky slopes of the Catskill Mountains long remained wild and desolate. Small settlements began in mountain valleys before the American Revolution. After the war, population grew ... More on HMDB

Jolly Cholly's Funland

Things To Do – Attleboro Falls, Massachusetts

The park occupied 12 acres. The Ferris Wheel, Kiddie Whip, Merry-Go-Round, kiddie boats, kiddie buggies and Sky Fighter were added in 1959 ... More on RollerCoasterDataBase

Northboro Recreation Dept

Health Club – Northborough, Massachusetts

Community based fitness program offers an array of fitness classes including Hatha Yoga. Classes are geared for beginner and intermediate students. Class structure includes breathing, asanas, relaxation ... More on YogaFinder

Boston Walking Tour: Boston Back Bay

Tours – Marlborough, Massachusetts

Carole Krause Ltd

Museums – Accord, New York

Ulster County Courthouse

Landmarks – Kingston, New York

Stone building, site of the inauguration on New York's ... More on Yahoo! Travel

Locomotions Sports Bar

Restaurants – Cobleskill, New York

Good food good people good times!! More on Yahoo! Travel

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  • Crowd picks up when the students go back to college since it is the main attraction for Cobbleskill College. More on Yahoo! Travel

  • Best bar in Cobleskill. Good food good people good times!! More on Yahoo! Travel

Beach Plum Bakery

Restaurants – Cataumet, Massachusetts

The Beach Plum Bakery and breakfast cafe has been in business since 1998 and has been a favorite ... More on Beachplum-bakery.com

3.5
1 source
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3.5 out of 5
overall rating
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3.5
overall rating
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China Taste

Restaurants – Marlborough, Massachusetts

A truly wonderful family restaurant well worth a travel to visit and partake the experience. More on Restaurantica

3.5
5 reviews
3 sources
Average Rating
3.5 out of 5
5 reviews
3 sources
Restaurantica
4.0
3+ reviews
CitySearch
3.5
overall rating
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  • This is the only Chinese restaurant my family and I eat at even now that we've moved! More on Yahoo! Travel

  • Best Chinese food around. Chicken and Cashews is super, so are the scallion pancakes. buffet at lunchtime. More on TripAdvisor

Thornton W. Burgess Society

Museums – East Sandwich, Massachusetts

Comfort Inn Glenmont/Albany

Things To Do – Glenmont, New York

Conference facilities. Air conditioned rooms, Non-smoking rooms available, TV More on iloveny.com