Directions from Gloucester, Massachusetts to Oyster Bay, 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.


Philipsburg Manor

Things To Do – Sleepy Hollow, New York

The staff were great and I loved the way they were all in period costumes. More on TripAdvisor

3.0
9 reviews
1 source
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3.0 out of 5
9 reviews
1 source
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  • There really was not much to do, especially considered the cost of the tickets for two adults and three c... More on TripAdvisor

  • Great place to spend a quiet afternoon. Check out the events calendar for seasonal highlights More on TripAdvisor

CurtainUp Kids

Music and Theater – New York, New York

My daughter had a great time doing the show. More on GoCityKids

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  • ...disorganized. I worried about my child's safety. More on GoCityKids

  • ...disorganized. I worried about my child's safety. More on GoCityKids

Essence of Yoga Studio Inc

Health Club – Holbrook, New York

Essence of Yoga Studio creates balance in your life. We offer Pre-natal, Restorative, Hot, Yoga for breast ... More on YogaFinder

Joseph Rodman Drake Park

Parks – New York, New York

Cummings Park

Parks – Stamford, Connecticut

Facilities include: beach with pavilions and snack bar, board walk and fishing pier, marina and ramp, tennis courts, handball and basketball ... More on Cityofstamford.org

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  • 'Cummings Park' is located in Stamford, Connecticut, USA. It is made up of about 79 acres (320,000 m) of shorefront property on Long Island Sound. The main attraction of the park is 'Cummings Beac... More on Wikipedia

Bridge: Oak Grove or Children's

Parks – Manchester, Connecticut

(Oak Grove or Children's, 25', 1967, 07-02-c) across Porter Brook at Oak Grove Nature Center SE of Manchester , Manchester Township, Hartford County, CT. CT83 N. 0.1 miles from jct with I384 exit 3 just S. of Manchester, E. on CT534 ... More on dalejtravis.com

Sachem Historical Society

Museums – Patchogue, New York

McKenna Park

Parks – Waltham, Massachusetts

This playground is in a busy business area so they wanted subtle earthy colors. Subtle certainly doesnt mean that this wont draw attention! Young children will flock to ... More on KaBoom.org

Sarah's Wine Bar, Upstairs @ Bernard's

Wine Bar – Ridgefield, Connecticut

Beautiful decor wonderful and gracious hosts! More on Yahoo! Travel

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  • The best in Ridgefield: A great place for fine dining. More on Yahoo! Travel

  • Simply the finest food and service in the Ridgefield area. Great wine list at not unreasonable prices-very innovative food with a definitive ... More on Yahoo! Travel

Mac Z NY LLC

Bars – New York, New York

La Guardia Airport

Things To Do – New York, New York

Frankly, not a big city guy, love the airport because it gets me out of the city. More on GeckoGo

4.0
2 reviews
1 source
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4.0 out of 5
2 reviews
1 source
GeckoGo
4.0
2+ reviews
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  • A very organized and robust airport. More on GeckoGo

  • La Guardia Airport is located in the Borough of Queens, New York City, bordering on Flushing Bay and Bowery... More on GoCityKids

Toc to Go

Restaurants – Roslindale, Massachusetts

Belltown Pizza

Restaurants – Stamford, Connecticut

that great neighborhood pizza shop... More on ChefMoz.org

3.0
2 reviews
2 sources
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3.0 out of 5
2 reviews
2 sources
CitySearch
3.5
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  • That great neighborhood pizza shop... More on ChefMoz.org

  • Hands down the best recipes and ingredients at this pizza place. More on TripAdvisor

Whitehorse Tavern

Bars – New York, New York

A co-worker of mine even went here for lunch, and she said it was a good burger and the bartenders called h... More on CitySearch

4.5
1 review
1 source
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4.5 out of 5
1 review
1 source
CitySearch
4.5
1+ reviews
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  • Good clean fun, or as clean as it gets for a tavern at least. More on CitySearch

  • Old style pub by Wall Street, what a shock! This place is great for company parties, as they have 3 seperat... More on CitySearch