Directions from Watkins Glen, New York to Stockbridge, Massachusetts





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.


Windsor State Forest

Parks – Williamsburg, Massachusetts

Deep in the rolling hills of the Berkshire highlands, Windsor State Forest's cascading waterfall at Windsor Jambs stands out for its spectacular beauty. Windsor Jambs Brook plunges through a 25-foot-wide gorge, with 80-foot-high granite ... More on mass.gov

Wahconah Park

Parks – Pittsfield, Massachusetts

Wahconah Park - Some venues that lure in the best and the brightest, venues that keep you coming back again and again, venues that offer top-notch service. This isn’t one of them. Wahconah Park, at 105 Wahconah St., is your garden-variety ... More on clubzone

Laurel Lake (Lee)

Parks – Lee, Massachusetts

This 170-acre alkaline great pond, also known as Scotch Pond or Scotts Pond, is privately owned and located just north of Route 20 in the heart of the Berkshires. Maximum depth is 53 feet; average ... More on AnglerWeb.com

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  • Laurel Lake (Rte. 20) and Benedict Pond (Willow St., South Lee) provide boating, fishing and swimming. Remember old-fashioned Main Street with a barber shop, hardware stores, a five and dime and fr... More on GoingToTheBeach.com

Gen. Henry Knox Trail

Parks – Blandford, Massachusetts

Inscription. Through this place passed, General Henry Knox, in the winter of, 1775 – 1776, to deliver to, General George Washington, at Cambridge, the train of artillery, from Fort Ticonderoga used, to force the British Army, ... More on HMDB

MARGARET LINDLEY PARK

Swimming – Williamstown, Massachusetts

The town has dug a nice big oval in a little stream (Hemlock Brook), lined it with sand, dammed one end, added more sand for kids to have a little "beach" to dig in. Lots of very shallow stuff, but deep enough to really swim laps ... More on SwimmingHoles.info

Lake House Guest Room

Things To Do – Ithaca, New York

On Cayuga Lake, we offer master suite with private entrance, deck, lounge chairs + cafe table. Includes queen bed with double pullout sofa and many ... More on iloveny.com

Cherry Plains

Things To Do – Averill Park, New York

I winced at this, and she told me since I was just biking I could park out in front of the park for free . More on trails.mtbr.com

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  • Trail access can be gained form almost anywhere on the dirt road loop that surrounds the park and wildlife management area. More on trails.mtbr.com

  • Any access is good access... try fire tower rd in west stephentown.. park at top of hill... just don't get shot.... As for the ... More on trails.mtbr.com

American Legion

Things To Do – Germantown, New York

Copake Country Club

Golf Courses – Craryville, New York

It's a good value , to be sure. More on golflink.com

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  • wonderful course well maintained Great resturant a must replay More on golflink.com

  • whoo! Copake Country Club has a very fast green. You had might has well go putt on concrete. The fairways are very, very fast which is good if can't drive the ball very far. I played the back nine ... More on golflink.com

Club Matrix

Things To Do – Albany, New York

Ithaca Sound Maze

Things To Do – Ithaca, New York

The Ithaca Sound Maze is a 'kinder and gentler' style corn maze which encourages spontaneous musical interactions using a number of interactive instruments and sound installations hidden throughou... More on Visitithaca.com

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  • The Ithaca Sound Maze is a 'kinder and gentler' style corn maze which encourages spontaneous musical interactions using a number of interactive instruments and sound installations hidden throughout... More on Visitithaca.com

Riverview Restaurant

Restaurants – Athens, New York

Took my two nieces ages 9 and 11 to dine at the cafe tonight. The girls ordered burgers. The burgers were freshly made on a real bakery bun/roll and served with hand cut fries. They are picky eaters s ... More on TripAdvisor

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Taverna Banfi

Restaurants – Ithaca, New York

If visiting Cornell University and you're unable to leave campus, then dining at the Statler Hotel at this ... More on TripAdvisor

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  • Will go back again and again for the lunch buffet. More on TripAdvisor

  • The smallest portions I have ever seen, and some of the most expensive food in Ithaca . It's good food, but... More on Yahoo! Travel

McDonald's

Restaurants – Lanesborough, Massachusetts

Berkshire Scenic Railway, Inc

Museums – Lenox, Massachusetts

All aboard for a scenic ride into history! Experience a side of the Berkshires that you won't see from your car. Our 90 minute, 20 mile roundtrip excursion between the picturesque towns of Lenox a... More on Leechamber.org

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  • On weekends and holidays (Memorial Day weekend through the last weekend in October) the Museum offers two ninety minute round trip excursions from Lenox Station to Stockbridge and a forty-five ... More on familydaysoutusa