Directions from South Yarmouth, 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.


Arrowhead

Things To Do – Pittsfield, Massachusetts

My family and I stopped here before heading to a concert at Tanglewood. It was my second visit, as I'd been... More on TripAdvisor

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  • We visited Arrowhead over Memorial Day weekend in 2007. We really enjoyed the tour ($15/adults) although yo... More on TripAdvisor

  • Herman Melville bought this 18th-century house in 1850 and lived here until 1863. It was during this time ... More on Frommers

The Croff House

Things To Do – Hudson, New York

Combining the luxury of a boutique hotel and the personalized service of a B&B. Located on a quiet cul-de-sac. Five well appointed guest rooms and several common areas create the perfect atmosphere to relax and ... More on iloveny.com

Alpine Osteria Bed and Breakfast

Things To Do – Highmount, New York

7 Rooms. All with private baths. Immaculate accommodations. Dining room, lounge. Fireplace. Game room. ... More on iloveny.com

Dunkin' Donuts

Donuts – Pocasset, Massachusetts

Budget Blinds

Home and Garden Stores – Wilbraham, Massachusetts

Mansfield Galion Drive-In

Things To Do – Mansfield, Massachusetts

Screens: 1 Sound: Car Capacity: 500 Typical season: Technical details: none Mansfield Galion Drive-In Timeline: There are no ... More on drive-ins.com

Norwich Pond

Things To Do – Huntington, Massachusetts

This 122-acre natural great pond is located a little over a mile north of Route 66 in Huntington. Average depth is 17 feet; maximum depth is 53 feet. The water is of excellent quality, fairly clear, and transparent to 12 feet. Aquatic ... More on AnglerWeb.com

Farmer's Little House B&B

Things To Do – Catskill, New York

64 acres of forest, meadows & river. Relax in a hammock, dangle your feet in the pristine river, take a nature walk through wooded trails, or put ... More on iloveny.com

Whip City Brew Incorporated

Bars – Westfield, Massachusetts

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Triple Nickel Miniature Golf

Golf Courses – New Lebanon, New York

18 Hole miniature golf & golf learning center - Nestled on 9 acres in the scenic Lebanon Valley - Computerized analysis & video imaging - Kay McMahon, director of golf is the ... More on entertainment.com

Dairy Queen

Ice Cream – Chicopee, Massachusetts

Piccadilly Pub Restaurant

Restaurants – Marlborough, Massachusetts

Bar is separate from the dining area which is nice. More on Yahoo! Travel

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  • I love going here just for soup and salad! More on TripAdvisor

  • Been to this location a few times and it just gets worse. Drenched Ceasar salads, the Turkey dinner once up... More on TripAdvisor

Lucia's Pizza

Restaurants – Hurley, New York

Dunkin Donuts

Restaurants – Ludlow, Massachusetts

Clean place good food Happy people. More on Yahoo! Travel

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  • Clean place good food Happy people. Love going there. Pat More on Yahoo! Travel

Mount Tom State Reservation

Parks – Holyoke, Massachusetts

For all there are many hiking trails short long difficult and easy. The rangers are there to advise you if you have question and tour with if you need to. The entrance fee is 3 dollars per car or l... More on TripAdvisor

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  • Nice beach, great views from the tower good picnicing More on TripAdvisor

  • Mt. Tom boasts an unparalleled view of the Connecticut Valley north and south, the Berkshire mountains to the west and the Pelham hills to the east. This 2,082 acre facility offers 20 miles of hiki... More on mass.gov