East Coast Leg 1: Portland to Boston

  • 34
  • 07:01
  • 198 mi
  • $36
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Created by Tatiana Danger - February 10th 2019

Maine is a state famous for its forests, its mountains, and its lobster. It's not the first place you think of when you're looking for a sophisticated art scene or a great shopping experience. But Portland, Maine's largest city, is full of wonders to be explored. Cobblestone streets, old bookstores, art galleries and specialty boutiques are all part of the Old Port District. Stroll the streets and explore the shops, and eat your way through this charming neighborhood. Outdoor lovers can also explore Casco Bay and its many islands by navigating the local ferry system, or taking a scenic cruise. If you visit Peak Island, plan to rent a golf cart or bring your bike, because there is a lot to see.

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0mi 00h 02m
Photo of Old Port
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50 Wharf St, Portland, ME, US

Old Port

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0mi 00h 03m
Photo of Portland Museum of Art
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7 Congress Sq, Portland, ME, US

Portland Museum of Art

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Portland has plenty of art galleries, boutiques, and craft shops, but it also has some great museums. The Portland Museum of Art is a small but quality museum with an eclectic mix of local artists and some beautiful pieces by more famous artists as well. The Native American Collection is especially popular. You can also visit the Winslow Homer Studio, where Homer painted many of his famous works. Or check out the Museum of African Culture, a small but surprising museum with a fascinating collection.

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390 Commercial St, Portland, ME, US

Becky's Diner

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0mi 00h 04m
Photo of Inn On Carleton
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46 Carleton St, Portland, ME, US

Inn On Carleton

FastBook
$$

Click to discover a
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1mi 00h 06m
Photo of International Cryptozoology Museum
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4 Thompson's Point Road Suite 106, Portland, ME, US

International Cryptozoology Museum

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3mi 00h 14m

194 Park Ave, Portland, ME, US

The Holy Donut

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1mi 00h 13m
Photo of Portland Observatory Museum
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138 Congress St, Portland, ME, US

Portland Observatory Museum

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1mi 00h 07m
Photo of Victoria Mansion
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109 Danforth St, Portland, ME, US

Victoria Mansion

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Portland is an old town, with some stellar architecture and historically significant buildings. The Victoria Mansion is a beautiful house from before the Civil War. If you like visiting historic homes, this is one of the best in the area. The Portland Observatory has been providing amazing views since 1807. If you're interested in poetry, the Wadsworth-Longfellow House is also located in Portland.

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4mi 00h 10m

1000 Shore Rd, Cape Elizabeth, ME, US

Portland Head Light

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17mi 00h 33m
Photo of Palace Playland
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1 Old Orchard St, Old Orchard Beach, ME, US

Palace Playland

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A great spot to end your trip is Old Orchard Beach and Palace Playland, which is the only New England amusement park that's directly on the beach. Then you've got Portland, ME (visit the Old Port district to get a taste of New England, the vibe here is very 19th century), and then you're driving along the Kennebec River after passing Augusta and Waterville.

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18mi 00h 28m
Photo of Wedding Cake House
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105 Summer St, Kennebunk, ME, US

Wedding Cake House

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2 Western Ave, Kennebunk, ME, US

Clam Shack

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22mi 00h 31m
Photo of Wiggly Bridge and Steedman Woods
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Old Mill Rd, York Harbor, ME, US

Wiggly Bridge and Steedman Woods

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10mi 00h 14m

8 Congress St, Portsmouth, NH, US

Popovers On the Square

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14mi 00h 18m
Photo of Memorial to a Witch
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40 Park Ave, Hampton, NH, US

Memorial to a Witch

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The New Hampshire stretch of I-95 is also pretty short, but along the route are a couple cool places worth stopping at. First check out this Memorial to a Witch in Hampton, NH. It's just a simple unmarked stone monument dedicated to Eunice "Goody" Cole, AKA "the witch of Hampton", who was accused of witchcraft in 1656. That ruling was eventually overturned... in 1938.

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30mi 00h 45m
Photo of Crane Beach
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290 Argilla Rd, Ipswich, MA, US

Crane Beach

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Photo of Castle Hill on the Crane Estate
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290 Argilla Rd, Ipswich, MA 01938, Ipswich, MA, US

Castle Hill on the Crane Estate

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2mi 00h 09m
Photo of Russell Orchards
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143 Argilla Rd, Ipswich, MA, US

Russell Orchards

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51 Linebrook Rd, Ipswich, MA, US

1640 Hart House

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Fun factoids: The first American lighthouse was built in Boston Harbor in 1716. The Fig Newton is named after a Boston suburb. Boston is home to the oldest public park in the US. Revere Beach in Boston was the country’s first public beach. Fenway Park which was opened in 1912 is the oldest original Major League Baseball stadium still in use. Popular Foods include: Clam Chowder; Lobster Roll.

Tatiana Danger

Roadtrippers co-founder. When I grow up I'm going to be Indiana Jones or a professional pizza tester. Current Status: Mom to Bruce and Nina.