Directions from Gloucester, Massachusetts to Cairo, 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.


Rainbow Connection

Bars – Indian Orchard, Massachusetts

Love the atmosphere ~ very comfortable. More on CitySearch

4.5
1 review
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4.5 out of 5
1 review
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4.5
1+ reviews
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  • Love the atmosphere~ very comfortable. DJ Jimmy is great on Saturdays- luv him! More on CitySearch

  • Rainbow Connection - Happy hour never looked so good. Rainbow Connection, located at 186 Main St caters to ... More on clubzone

YMCA of Greater Westfield

Swimming – Westfield, Massachusetts

Berkshire Bach Society

Things To Do – Great Barrington, Massachusetts

Year round performances of the vast repertoire of choral & instrumental music by J. S. Bach & those in ... More on Berkshires.org

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  • Year round performances of the vast repertoire of choral & instrumental music by J. S. Bach & those ... More on uptake_content

Dunkin' Donuts

Donuts – Albany, New York

3.5
1 source
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3.5 out of 5
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3.5
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Gen. Henry Knox Trail

Landmarks – Framingham, 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

Shaker Farms Country Club

Golf Courses – Westfield, Massachusetts

The staff was very friendly and I will definatly be going back to play there again this year. More on golflink.com

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  • Wanted to demand my money back but just learned a valuable lesson instead. More on golflink.com

  • Not a bad course More on golflink.com

The Dublin Underground (Savannah's)

Nightlife – Albany, New York

One of Albany's finest restaurants/bar, and nightlife venue. Drink specials, live music, DJs, VJs, ... More on iloveny.com

Rhinebeck Farmers Market

Food Shopping – Rhinebeck, New York

Market features products from local growers and producers, including fruits, raw honey and bee products, wine, cut flowers, ... More on iloveny.com

Boston Workmen's Circle

Things To Do – Brookline, Massachusetts

about Boston Workmen's Circle: The Boston Workmen's Circle Center for Jewish Culture and Social Justice is a thriving community rooted in our shared heritage and ... More on GoCityKids

Route Seven Diner

Restaurants – Latham, New York

Carvel Ice Cream Bakery

Restaurants – Malden, Massachusetts

In Short :Tom Carvel was inspired to found a freestanding ice cream store after his ice cream truck suffere... More on CitySearch

3.5
1 source
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3.5 out of 5
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3.5
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  • Carvel Ice Cream Bakery is your headquarters for ice cream treats. Carvel ice cream cakes are the preferred... More on Yahoo! Travel

Union Bar & Grill

Restaurants – Great Barrington, Massachusetts

New ownership has brought with it a new vibrant pasta regimine while not messing with the classic ribs, oys... More on CitySearch

4.5
1 review
1 source
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4.5 out of 5
1 review
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4.5
1+ reviews
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  • The food is fantastic . More on CitySearch

  • the weekend pace is fast, upbeat, almost frenetic. the food is fantastic. new ownership has brought with it... More on CitySearch

Blue Dolphin Charters

Things To Do – Ulster, New York

Sunset cruises - Sightseeing - Custom fishing charters - Brunch & dinner trips available to area waterfront restaurants - Your group, up to 6 people, can view ... More on entertainment.com

The Big E

Everything for the horse lover (Seminars and trade show). Worth the trip! More on TripAdvisor

3.0
10 reviews
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3.0 out of 5
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  • If you're reading this review then I am going to guess that you haven't been to the Big E before. Those of ... More on TripAdvisor