Directions from Boston, Massachusetts to Rhinebeck, 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.


The Land of Nod Winery

Wineries And Vineyards – East Canaan, Connecticut

GLENDALE FALLS

Swimming – Chester, Massachusetts

Beautiful cascading falls with large but shallow pool at the bottom, also some pools in falls above. ... More on SwimmingHoles.info

Eleanor Roosevelt National Historic Site

Museums – West Park, New York

'Eleanor Roosevelt National Historic Site' ('Val-Kill') consists of approximately two miles east of Springwood, ... More on Wikipedia

Hornest Nest Paintball

Themeparks – Ancramdale, New York

100 acre paintball facility, both indoor and out door airball fields, X- ball field, bunker fields, Castle on a hill, Western town and a lost convoy with duece and a half army trucks. ADMISSION: Fridays are free with a student I.D. ... More on Warpig.com

Rising Star

Health Club – Great Barrington, Massachusetts

Chris teaches the certification program for Lotus Palm Thai Yoga Bodywork throughout the United States. He teaches yoga in the Kripalu tradition and does Spiritual Lifestyle training at the Kripalu Center. ... More on YogaFinder

Akin Hall

Landmarks – Pawling, New York

Inscription. Akin Hall, Built and Dedicated in 1881, By A. J. Akin. Used by Christ, Church Since 1895. Moved to, Former Site of Mizzentop, Hotel by Lowell Thomas 1936. Akin Hall, Association 1986, , Erected 1986 by Akin Hall Asociation. ... More on HMDB

Millwood Farms Golf Course

Golf Courses – Framingham, Massachusetts

Its really tight actually and one errant drive and your hitting into a parking lot (hacks beware!). More on GolfReview

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  • The course is well maintained. More on GolfReview

  • This was one of the three worst courses ive ever played along with tyngsboro country club and stowaway. The greens are amazingly slow. The cuts on the course are I believe ... More on golflink.com

Gen. Henry Knox Trail

Landmarks – North Egremont, 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

Hotel Sierra

Things To Do – Fishkill, New York

135 suites/rooms. Full kitchen, Magic Slumber Beds, DVD, wired/wireless high-speed internet, meeting rooms, indoor pool, whirlpool, complimentary ... More on iloveny.com

Madam Brett Homestead

Museums – Beacon, New York

Built in 1709, Dutchess County's oldest homestead; 17 rooms of furnishings, porcelain, paintings, books, tools and gardens. ... More on Dutchesstourism.com

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  • Built in 1709, Dutchess County's oldest homestead; 17 rooms of furnishings, porcelain, paintings, books, tools and gardens. Owned ... More on iloveny.com

Sturbridge Isle Restaurant

Restaurants – Sturbridge, Massachusetts

3.5
1 source
Average Rating
3.5 out of 5
overall rating
CitySearch
3.5
overall rating
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Vitoria

Restaurants – Marlborough, Massachusetts

3.5
1 source
Average Rating
3.5 out of 5
overall rating
CitySearch
3.5
overall rating
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Bertucci's Brick Oven Restaurant

Restaurants – Framingham, Massachusetts

Made reservation here two weeks in advance and confirmed day before for 20 people. Upon arrival, we were to... More on TripAdvisor

3.5
5 reviews
2 sources
Average Rating
3.5 out of 5
5 reviews
2 sources
CitySearch
4.5
overall rating
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  • Service was terrible 10 minutes just for a drink fountain coke we ordered pizza which was wrong and what it... More on TripAdvisor

  • The Scene :With over a dozen locations in the greater Boston area, diners don't have to travel far to enjoy... More on CitySearch