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Essential Cultural Icons Road Trip: NYC - Boston - Portland

  • 15
  • 08:17
  • 396 mi
  • $65
Take This Trip

Created by Chevy Cruze - June 6th 2017

Nobody does history and culture quite like New England. Not only do they have a lot of personality and distinctive qualities, but they're also proud of their past, and do a lot to preserve it for the future. Take advantage and enjoy this trip, which will introduce you to authors' homes, retro diners, castles, and plenty more.

New York is the perfect place to kick off this adventure. Get ready for an unforgettable trip!

1
45mi 01h 00m

199 Elm St, Stamford, CT, US

The Glass House

1

The Glass House was designed by Philip Johnson in 1949, and was a landmark for modern architecture. The mostly glass one-room home is now owned by the National Trust for Historic Preservation, and they offer tours and events and display art here. It's a wild building and one that deserves every ounce of awe it inspires.

2
37mi 00h 47m

1140 Chapel St, New Haven, CT, US

Book Trader Cafe

2

A favorite hangout for Yale students, the Book Trader Cafe is a great place to rest and refuel after time spent on the road. Buy a used book to browse while you munch on a sandwich, pastry, or something caffeinated. If you feel so inclined, take some time to explore Yale's campus while you're at it.

3
42mi 00h 45m
Photo of Mark Twain House & Museum
4.5

351 Farmington Ave, Hartford, CT, US

Mark Twain House & Museum

3

The Mark Twain House & Museum in Hartford is where the famed author lived between 1874 to 1891, penning some of his most famous works (like The Adventures of Tom Sawyer and The Adventures of Huckleberry Finn) here. Tour the huge, opulent estate, and make sure to linger in the billiards room, where he did most of his writing.

4
63mi 01h 05m

300 Southbridge St, Worcester, MA, US

Miss Worcester Diner

4

Miss Worcester Diner is located in a classic lunch car, and it's been serving grub to hungry locals since 1950. They offer various flavors of French toast, all of which are absolutely to die for (especially the crunchy French toast), in addition to omelets, corned beef hash, eggs Benedict, and other diner staples.

5
39mi 00h 46m
Photo of Walden Pond
4.1

1169 Market Ave, MA, US

Walden Pond

5

Walden Pond is the location where Henry David Thoreau lived when he was inspired to write Walden, a book that promoted the Transcendentalist movement and the idea of natural conservation. Stroll around the serene and lovely pond to find his cabin, and soak up as much inspiration as possible!

6
19mi 00h 29m

Whether you grab some chowdah or browse the offerings at Faneuil Hall, Boston is loaded with culture, history, and delicious local eats.

7
0mi 00h 02m
Photo of The Liberty Hotel
4.0

215 Charles Street, Boston, MA, US

The Liberty Hotel

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7

The Liberty Hotel is an extra-special experience, and you won't find another spot like it. That's because it's a former prison turned luxury hotel! The lobby is gorgeous, and cheeky, jail-themed touches throughout are super quirky.

8
33mi 00h 48m

80 Hesperus Ave, Gloucester, MA, US

Hammond Castle Museum

8

Hammond Castle was the private home of John Hays Hammond Jr., one of America's most prolific inventors (the only American with more patents than him is Thomas Edison!) The castle is filled with art he collected from his travels and surrounded by lush gardens. If you take the guided tour, you'll get special insight into the quirky and strange man behind the patents, and why he's known as the Father of Radio Control.

9
12mi 00h 24m

143 Argilla Rd, Ipswich, MA, US

Russell Orchards

9

Even though apples won't be in season until the fall, Russell Orchards still has has fruit wines for tasting, berry picking, a little general store with various goods for sale, and, of course, their famous cider donuts.

10
38mi 00h 48m
Photo of  USS Albacore
4.5

600 Market Street Portsmouth, Portsmouth, NH, US

USS Albacore

10

A cool bit of military history is the USS Albacore. This research submarine, developed in 1950, was designed by the Navy to test features that are still used in subs today. It was finally decommissioned in the 1970s, after years of tests and tweaks, and you can now tour the Albacore for yourself!

11
28mi 00h 34m

2 Western Ave, Kennebunk, ME, US

Clam Shack

11

Right at the edge of the Kennebunk River, the Clam Shack is a classic seafood joint, specializing in boxes of fried deliciousness and lobster rolls, with fresh, sweet lobster on a fluffy homemade roll doused in butter and mayo. Eat it at a picnic table outside, the way it was meant to be enjoyed.

12
16mi 00h 25m

93 Buxton Rd, Saco, ME, US

Way Way Store

12

The Way Way Store has been charming visitors and locals alike since it opened in the 1920s. The unique building, with its handmade touches, is on the National Register of Historic Places, and it's a great little spot for ice cream, souvenirs, and penny candy. Check out the original cash register still sitting on the counter!

13
18mi 00h 23m
Photo of Portland Regency Hotel & Spa
3.8

20 Milk Street, Portland, ME, US

Portland Regency Hotel & Spa

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13

The Portland Regency Hotel & Spa is right near the water, which makes for some killer views. It also features an amazing spa, a swanky martini lounge, and a location in an old, 19th-century armory.

0mi 00h 02m

Portland at last! This city has loads of history and plenty of gorgeous old Victorian buildings to explore. Stroll Congress Street or Commercial Street to uncover some cool gems! And, of course, grab a lobster roll and some blueberry pie.