Directions from Montauk, New York to Gloucester, Massachusetts





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.


Friendly's

Ice Cream – Watertown, Massachusetts

Friendly's is amazing. From breakfast to lunch, dinner, and dessert, Friendly's will never let you down. I looove their ice cream. My favorite is the Chicken Salad and ... More on GoCityKids

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  • True to its name, Friendly's is a great place to catch a bite with the kids. The restaurant caters to families with a hankering for burgers, fries, and dairy delights. Based in Massachusetts, Frien... More on GoCityKids

  • about Friendly's: True to its name, Friendly's is a great place to catch a bite with the kids. The restaurant caters to families with a hankering for burgers, fries, and dairy delights. Based in Ma... More on GoCityKids

Apple Annie

Farm – Brentwood, New Hampshire

Low spray apples, cider, baked goods, jams, jellies, pumpkins, vegetables, PYO, farm market. More on allaboutapples.com

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  • Pumpkins Open 9am-6pm, daily, September-November (apple season) Low spray apples. Special Events: School tours by appointment; picnic ... More on pumpkinpatchesandmore.org

Christmas Dove (The)

Childrens Museums – Boston, Massachusetts

The store is filled with what seems everything you could think of, set in theme rooms and the personnel is ... More on Yahoo! Travel

5.0
2 reviews
1 source
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5.0 out of 5
2 reviews
1 source
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5.0
2+ reviews
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  • Like nothing else you've ever imagined. What a store!!!! More on Yahoo! Travel

  • We travel from Long Island to Quincey Market and Faniell Hall every year on Halloween weekend, The Christma... More on Yahoo! Travel

Moonlight Productions

Music and Theater – Ipswich, Massachusetts

about Moonlight Productions: Founded in 1996, Moonlight Productions is a non-profit intergenerational theater that is dedicated to mentoring kids and teens through musical productions. They have fo... More on GoCityKids

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  • ABOUT MOONLIGHT (Read more about principals: JT Turner Sandi Nason Founded in 1996, moonlight productions is a non-profit intergenerational theater started by JT Turner and Sandi Nason. The company... More on Moonlightproductions.org

Masonic Temple Association

Religion and Faith – Andover, Massachusetts

Club of Odd Volumes

Things To Do – Boston, Massachusetts

Dairy Queen

Ice Cream – Boston, Massachusetts

about Dairy Queen: Who doesn't love a Blizzard ? Because the majority of Dairy Queen restaurants are individually owned and operated franchises, quality, hours, and offerings vary greatly - you probably know what you like (or don't) ... More on GoCityKids

First Seventh Day Baptist Church of Hopkinton 1622-1935

Landmarks – Ashaway, Rhode Island

Inscription. Seventh Day Baptists, members of a church of like faith in Newport, Rhode Island until 1708, first worshipped in this community in 1672. The first meeting house was built in 1680. The nearby-by church, which replaced ... More on HMDB

Fort McClary State Historic Site

Parks – Kittery, Maine

Sure, we make use of rest stops (very handy for basic needs) and service centers (commercial versions of th... More on Epinions.com

4.0
2 reviews
2 sources
Average Rating
4.0 out of 5
2 reviews
2 sources
Epinions.com
4.0
1+ reviews
Epinions.com
4.0
1+ reviews
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  • When we do road trips, we always on the lookout for places to stop that serve to enhance our holiday experi... More on Epinions.com

  • When we do road trips, we’re always on the lookout for places to stop that serve to enhance our holiday... More on Epinions.com

Walden Pond

Things To Do – Boston, Massachusetts

On July 3 at Walden Pond, I was delighted to find a parking area with few cars. More on igougo

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  • When I arrived around 8:45 A.M. on July 3 at Walden Pond, I was delighted to find a parking area with few cars. I chose my spot ... More on igougo

  • If you haven't studied it in American literature, you'll probably remember it from Dead Poet's Society: I went to the woods because ... More on igougo

Mashashimuet Park

Things To Do – Sag Harbor, New York

Al's Family Diner

Restaurants – Methuen, Massachusetts

Been here once its pretty good if you like to eat out. More on Yahoo! Travel

4.5
1 source
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4.5 out of 5
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4.5
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  • Been here once its pretty good if you like to eat out. More on Yahoo! Travel

  • Was always treated well!: Before i moved out of the area I went here as often as i could afford. The portio... More on Yahoo! Travel

Dunkin Donuts

Restaurants – Lynn, Massachusetts

Kingston Pizza of Westerly

Restaurants – Westerly, Rhode Island

3.5
1 source
Average Rating
3.5 out of 5
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3.5
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