Directions from Gloucester, Massachusetts to Milford, 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.


Wickaboag Pond

Beaches – West Brookfield, Massachusetts

This 320-acre warm water pond is located just north of Route 9, about a quarter mile west of West Brookfield Center. The pond is characterized by light brown watercolor with a transparency of eight feet. The mean and maximum depths ... More on AnglerWeb.com

Waltham Museum

Museums – Waltham, Massachusetts

Located in the old Waltham Police Station, the museum displays an extensive collection of memorabilia from Waltham's past, including automobiles, sports, military, and civic, plus highlights on th... More on Discoverwaltham.com

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  • Located in the old Waltham Police Station, the museum displays an extensive collection of memorabilia from Waltham's past, including automobiles, sports, military, and civic, plus highlights on the... More on uptake_content

Josiah Nelson House

Landmarks – Lincoln, Massachusetts

Inscription. This was the site of Josiah and Elizabeth Nelsons home. Josiah was a farmer as well as a housewright – a person who built and repaired houses. According to family tradition, when a party of men on horseback was ... More on HMDB

A Room With A View Bed & Breakfast

Things To Do – Schenectady, New York

Three guest rooms with a blend of contemporary and antique furnishings, private balconies, cable TV ... More on iloveny.com

Cur Non?

Landmarks – Schenectady, New York

Inscription. Cur Non! On June 11, 1825, Major General, Marquis De Lafayette, Soldier, Statesman, Citizen of France, And of the United States, Was the Guest of the, Honorable Joseph C. Yates, Governor of The, State of New York. Erected ... More on HMDB

East Branch Delaware River

National And State Parks – Roxbury, New York

The East Branch Delaware River, approximately 75 miles (120 km) long in the U.S. state of New York, is one of two branches, along with the West Branch, that join to form the Delaware River. It flows through a mountainous area on the ... More on AnglerWeb.com

Sola for Men

Clothing Shopping – Cambridge, Massachusetts

A companion store to the women's boutique, Jasmine Sola , this is one-stop shopping for hip, ... More on Yahoo! Travel

Urban Music Together

Music and Theater – Jamaica Plain, Massachusetts

about Urban Music Together: Urban Music Together is a Music Together Center which serves families in Jamaica Plain and neighboring Roslindale. Classes for infants through preschoolers include songs... More on GoCityKids

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  • We offer additional Music Together � classes at the Tony Williams Dance Center in the Brewery. More on Urbanmusictogether.com

Finagle-A-Bagel

Restaurants – Burlington, Massachusetts

This bagel chain's expansive menu lures carb-loving ... More on Gayot

The Coach Grill

Restaurants – Wayland, Massachusetts

Showed up on time for a weekday reservation wearing appropriate garb for any city restaurant-jeans, boots, ... More on CitySearch

3.5
15 reviews
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3.5 out of 5
15 reviews
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4.5
5+ reviews
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  • The ambiance is not too stuffy or pretensious. More on Yahoo! Travel

  • Don't even think about it! The place is NOT a quality food place as looks might have you believe. Our steak... More on CitySearch

Watertown House of Pizza

Restaurants – Watertown, Massachusetts

Should win an award of money and a troffy. More on Yahoo! Travel

3.5
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3.5 out of 5
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3.5
overall rating
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  • Owners are really nice. Pizza isn't greasy.Should win an award of money and a troffy. They have good calzon... More on Yahoo! Travel

Corey Hill Playground

Parks – Brookline, Massachusetts

When I first moved to Summit 3 long years ago, a cab driver told me it was the absolute best view of Boston. More on KidsPlayParks

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  • I've come back since several times, alone, with family, with friends, and it's always a delight to reach the cute park at the top after the climb. More on KidsPlayParks

  • As a Boston n00b two years ago, I decided to include Summit Ave in my running route not realizing that it is named Summit for a reason. After the bigg est hill workout of my life, I was rewarded wi... More on KidsPlayParks