Remove Ads

Offbeat Road Trip: NYC - Boston - Portland

  • 15
  • 10:28
  • 513 mi
  • $86
Take This Trip

Created by Chevy Cruze - June 8th 2017

So, you like to adventure off the beaten path... that's cool, then this New York to Portland trip is for you! It's got a little bit of everything: weird eats, crazy towns, mysterious castles, and more. Oh, and if you do take on this route... say hi to Bigfoot for us.

New York has some pretty weird attractions... but once you hit the road, you'll get to experience a whole other world of oddities.

1
59mi 01h 16m
Photo of Vatican Gardens Knockoff
3.8

2539 Park Ave, Bridgeport, CT, US

Vatican Gardens Knockoff

1

St. Margaret's Shrine (or, as some call it, the Vatican Gardens Knockoff) is a collection of statues depicting religious imagery (think, stations of the cross and assorted miracles), complete with plants, a waterfall, and a footbridge. It was once in ruin, but has recently been fixed up... and it's an odd little photo op.

2
75mi 01h 23m

56 W Main St, Mystic, CT, US

Mystic Pizza

2

Head to Mystic for Mystic Pizza... yes, like the movie! Screenwriter Amy Jones based the film, filmed in and around Mystic, on this little local joint, and it's remained a hit since then. And trust us, the pizza isn't all hype. It's actually delicious.

3
65mi 01h 09m
Photo of Lizzie Borden Bed & Breakfast Museum
4.5

230 2nd St, Fall River, MA, US

Lizzie Borden Bed & Breakfast Museum

FastBook
$$$

Click to discover a
great deal!

3

Fans of horror, true crime, ghosts, and mysteries will likely recognize the name Lizzie Borden... but are you brave enough to stay the night in the house where she (allegedly) hacked her parents to death with an axe? This antique B&B/museum is supposedly haunted... you've been warned.

4
52mi 01h 06m
Photo of Lake Chargoggagoggmanchauggagoggchaubunagungamaugg
3.8
4

Welcome to Lake Chargoggagoggmanchauggagoggchaubunagungamaugg... but you can just call it Lake Webster. That's what the locals do, since most can barely pronounce it, let alone spell it. It's officially America's longest place name, which roughly translates from an Old Native American language to "Englishmen at Manchaug at the Fishing Place at the Boundary".

5
58mi 01h 08m

55 Davis Square, Somerville, MA, US

Museum of Bad Art

5

"Celebrate the labor of artists whose work would be displayed and appreciated in no other forum" at Somerville's Museum of Bad Art. All the pieces here are sincere (i.e. not intentionally dumb) and are spectacularly awful.

6
10mi 00h 20m

Stop off in Beatown, home to lots of weird and wonderful things. Check out the Boston Molasses Disaster memorial or the skull of Phineas Gage at the Warren Anatomical Museum.

7
5mi 00h 11m
Photo of The Liberty Hotel
4.0

215 Charles Street, Boston, MA, US

The Liberty Hotel

FastBook
$$$$

Click to discover a
great deal!

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
18mi 00h 25m

255 Newbury St, Danvers, MA, US

Putnam Pantry Candies & Ice Cream

8

This local gem is located on the property where an American General from the Revolutionary War was born. Today, they make mouthwatering candies and sundaes, including a 17 scoop monster they call "The Battle of Bunker Hill".

9
32mi 00h 44m
Photo of America's Stonehenge
3.0

105 Haverhill Rd, Derry, NH, US

America's Stonehenge

9

"A maze of man-made chambers, walls and ceremonial meeting places, America's Stonehenge is most likely the oldest man-made construction in the United States (over 4000 years old)." It's covered in strange inscriptions and has astrological significance, just like the OG Stonehenge.

10
68mi 01h 24m

9 Mills Rd, Kennebunkport, ME, US

Nunan's Lobster Hut

10

For the quintessential Maine lobster experience, head to Nunan's Lobster Hut. Operating out of the same adorable seaside shack since the 1950s, they serve a menu of insanely fresh seafood staples and, of course, blueberry pie and cobbler.

11
27mi 00h 36m

32 Resurgam Pl, Portland, ME, US

International Cryptozoology Museum

11

The International Cryptozoology Museum is a collection of objects and artifacts alike, all relating to cryptids like Bigfoot, the Loch Ness Monster, and more. You'll great a great overview of some of the evidence for these beasts, and info on their portrayal in pop culture. Definitely make a point to talk to the owner, if he's there. He's a fascinating person, and a font of odd knowledge.

12
19mi 00h 23m
Photo of Desert Of Maine
3.5

95 Desert Rd, Freeport, ME, US

Desert Of Maine

12

The Desert of Maine is a true oddity. It's not an actual desert (more the result of bad farming practices) but this place added in some fun kitsch that makes it an excellent attraction. See the camels, the world sand collection, mine for gems, camp out, or just pick up a fun souvenir at the gift shop after strolling the dunes.

13
17mi 00h 21m
Photo of Portland Regency Hotel & Spa
3.8

20 Milk Street, Portland, ME, US

Portland Regency Hotel & Spa

FastBook
$$$

Click to discover a
great deal!

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! Unwind from your unexpected and exciting adventure with some quiet time near the Atlantic Ocean.