Directions from Gloucester, Massachusetts to Monroe, 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.


Matrix

Dancing – Poughkeepsie, New York

Matrix - Maatrix is Hudson Valley’s premiere spot to moonlight every Saturday night! Doors open at 10:00 pm and remain open until 4:00 am. The Matrix has two rooms along with a lounge, V.I.P. where Hip Hop, R&B, Techno, Trance, and ... More on clubzone

Coles Mill

Parks – Pawling, New York

Inscription. Founded 1842 by Emery Cole, Ruins 870 ft. west, Produced flour, feed & grain, Wagonmaking shop added, run by son, Albert S. Cole, , Erected by Mr & Mrs Robert Williams. , Location. 41° 34.038′ N, 73° 36.873′ ... More on HMDB

Sim's Health and Racquet

Swimming – Sturbridge, Massachusetts

Highlands Country Club

Golf Courses – Garrison, New York

As soon as we arrived, Jennifer met us with two glasses of champagne and she made sure that the staff kept ... More on TripAdvisor

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3.0 out of 5
9 reviews
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  • They even walked around the grounds to find my father (who was on a smoke break) so we could do our Father ... More on TripAdvisor

  • My husband and I were married at the Highlands on November 5, 2011. From the minute I spoke to Adrienne it ... More on TripAdvisor

Italian American Historical Society

Museums – West Hartford, Connecticut

Site of Cromline House

Landmarks – Chester, New York

Inscription. Built by Daniel Cromline, 1716, named Greycourt Inn. Before 1765 was main house between New Windsor and New Jersey, , Erected 1935 by State Education Department. , Location. 41° 22.66′ N, 74° 14.53′ ... More on HMDB

Drop In Skate Park‎

Skating – Nyack, New York

Headquarters of General George Washington

Landmarks – Wayne, New Jersey

Inscription. This brick Georgian mansion was built by Colonel Theunis Dey in 1742. It was used as headquarters by General George Washington from July 1 to July 29, 1780 and again from October 8 to ... More on HMDB

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  • The George Washington Papers at the Library of Congress Time Line: The American Revolution The Colonial Period The American Revolution The Early Republic 1774 1775 1776 1777 1778 1779 1780 1781 178... More on Memory.loc.gov

Bright Horizons at Sudbury

Things To Do – Sudbury, Massachusetts

about Bright Horizons at Sudbury: Bright Horizons Family Solutions manages more than 600 employee-sponsored child care centers throughout the United States. Their centers provide care for children ages six weeks to six years and are ... More on GoCityKids

CT Ballooning, LLC, Hartford, CT

Things To Do – Berlin, Connecticut

Purchase a � Pre-Paid Boarding Pass � from CT Ballooning today!! Give that special someone the gift of a lifetime. Our Boarding Pass is a great birthday, anniversary or wedding gift! Let them choos... More on Ctballooning.com

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  • Champagne Hot Air Balloon Rides with CT Ballooning There�s nothing like it in the world �" a hot air balloon ride is truly a one-of-a-kind experience! Come enjoy a spectacular sunrise hot air ballo... More on Ctballooning.com

West Roxbury YMCA

Health Club – West Roxbury, Massachusetts

What I liked best is that there was no per child charge and that everyone had a great time. More on GoCityKids

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  • We just had a gym party for my 9 year old at the Y. What I liked best is that there was no per child charge and that everyone had a great time. I got the package that include the moon bounce; we al... More on GoCityKids

  • about West Roxbury YMCA: This YMCA serves West Roxbury and the nearby communities of Roslindale and Dedham. It offers extensive child care options, sports programs, camps, and afterschool youth pro... More on GoCityKids

Anna Shea

Restaurants – Katonah, New York

There are too many fantastic little chocolates to name and describe. You must come here to look and sample for yourself. Let me add that in addition to the bon bons, Anna Shea offers sensational chocolate-robed ... More on RoadFood

Toscani and Sons

Restaurants – Poughkeepsie, New York

The Food Group

Restaurants – Spring Valley, New York