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Journey into historic beauty on this road trip back in time

From Toledo to Cleveland to Boston!

  • 20
  • 16:18
  • 867 mi
  • $145
Take This Trip

Created by Selena K - August 16th 2016

The best thing about traveling is that it gives people an opportunity to see more of the world in front of them. My mentality is, you’ll find so much beauty if you “get out there” more often. As a 21-year-old college kid from Toledo, Ohio, I take every chance I can to "get out there," and when the opportunity to take a road trip presented itself, I couldn't have been more ready; I set my sights on Boston.

Boston has always been high on my list of road trip destinations. I’ve always seen it as a pillar East Coast city, a place with great food, culture, people, and, of course, history – and I couldn’t have been more correct. Plus, as a photographer, I was eager to capture the city's unique beauty, and to find some unexpectedly beautiful spots that would transport me to another time and place along the way as well.

Toledo to Boston. The first thought that probably comes to your mind is, “wow, that’s a long drive.” And, yes, while it is a long drive, it is also beautiful. Though much of the route is on the turnpike, you still get to drive right along the gorgeous valleys of rural Pennsylvania and New York that look like they've been untouched by time. With the bad comes the good, right?

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119mi 01h 57m
Photo of Cuyahoga Valley National Park
4.5

6947 Riverview Road, Peninsula, OH, US

Cuyahoga Valley National Park

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For my first stop, I didn’t have to go far at all-- or that far back in time. Cuyahoga Valley National Park, just outside of Cleveland, Ohio, preserving 19th century farmland, is just gorgeous. Personally, it’s my favorite Ohio treasure. No matter the time or season, you’re destined for beauty. It’s so…quiet. Walking through the Cuyahoga Valley forest is so peaceful, especially when you make your way to Brandywine Falls or the winding Boston Mills (coincidence, right?) Road, my favorite route in the entire state of Ohio.

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9mi 00h 20m
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15mi 00h 24m
Photo of Melt Bar & Grilled
4.1

6700 Rockside Rd, Cleveland Heights, OH, US

Melt Bar & Grilled

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After hiking past the wonders of Cuyahoga Valley, you can cruise into Downtown Cleveland and check out Melt Bar and Grilled. I can personally guarantee you’ll have the best grilled cheese sandwich you never knew you wanted. It’s worth the stop, believe me.

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582mi 09h 51m

10 Hale Hill Rd, NH, US

Cathedral Of The Pines

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After New York, I swung through Vermont so I could swing by the Cathedral of The Pines. Defined as a “unique outdoor place of worship for people of all faiths,” Cathedral of The Pines is an outdoor gathering place nestled in the middle of a vast forest. Renowned photographer Gregory Crewdson completed a body of work there a couple years back, and so I wanted to see the land for myself. If you want to feel true solitude and comfort, I highly recommend a stop here.

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27mi 00h 41m
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90mi 01h 56m

I then made my way to Massachusetts and immediately was introduced to that special, quaint East Coast small-town feel as I cruised through the state's many little hamlets. You know, the Main Street, 1950's kind of towns - one coffee shop, a bookstore, a couple of restaurants and an auto mechanic. The east coast is full of ‘em, especially Massachusetts.

Boston is a whole other world, though. Once I crossed into town, I was taken away by the vastness. While Downtown Boston is very small and compact, the entire city of Boston spreads out so far it seems. Even at night, I could see nothing but buildings and traffic lights for miles.

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1mi 00h 05m
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2mi 00h 07m
Photo of Holiday Inn Boston Bunker Hill
3.7

30 Washington Street, Somerville, MA, US

Holiday Inn Boston Bunker Hill

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You know how New York has different boroughs like The Bronx, Queens, and Staten Island? Well, that’s how I felt with Boston. It’s so cool to be able to take a 10-minute subway ride and see something totally different. Each village is so unique.

The Holiday Inn furnished for me was located in the neighborhood of Somerville. It was a great experience; I felt welcomed and safe, since I was a 21-year old kid, in a big city all by myself…I knew nobody, nor did I know where anything was. I was talked through a subway system map, given pointers and places I should visit, and given recommendations for great restaurants, even. Oh, and did I mention how comfortable that bed was?

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1mi 00h 06m
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1mi 00h 05m
Photo of Boston Burger Company
4.1

37 Davis Sq, Somerville, MA, US

Boston Burger Company

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Somerville was easily my favorite village of Boston, almost solely based on the food. Being the burger connoisseur I am, I wandered into the Boston Burger Company. It didn’t take me long to figure out that it’d been featured on the Food Network show “Diners, Drive-Ins and Dives,” so I knew that it was gonna be good. Not even kidding you, they have probably 25 different burgers to choose from. My eye is attracted to peanut butter, and so I ordered “The King” - peanut butter, bacon, fried banana, and cinnamon sugar. Easily the best burger I’ve ever had in my life. I think it’s pretty safe to say, no matter what you get at Boston Burger Company, it’s going to be delicious.

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0mi 00h 00m

4A College Ave, Somerville, MA, US

J.P. Licks

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After my dinner, I walked next door and got a strawberry waffle cone from J.P. Licks. My hollow leg sure was coming in handy that night! After dinner and ice cream, you could grab a movie at the nearby Somerville Theatre, which oozes retro vibes.

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2mi 00h 08m
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3mi 00h 07m
Photo of Old State House
4.5

206 Washington St, Boston, MA, US

Old State House

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One thing that really struck me about the city was the history. It's so fascinating, especially when you get to experience all of it in person. Nestled right in the heart of a neighborhood, the Bunker Hill Memorial is beautiful. The Old State House, the first British building in the United States, is also amazing. Surrounded by skyscrapers, it’s interesting to see how developed Boston has become over the years.

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0mi 00h 01m
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0mi 00h 02m

33 Union St, Boston, MA, US

Saus

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I then found my way to the Haymarket subway stop and walk down to the Italian Village - it did not disappoint. It is just so neat. Tiny, winding brick roads, little houses, an assortment of Italian restaurants and culture. And, if you’re a history buff, Paul Revere’s house is there! It was just outside of the Italian Village where I had poutine for the first time at Saus, a popular eatery in town. French fries, cheese curds, chicken n’ beef gravy, and an egg, all mixed together. Talk about delicious.

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1mi 00h 07m
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1mi 00h 06m
Photo of Harvard University
4.5

Havard University, Cambridge, MA, US

Harvard University

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One of the most unique things to see near Boston is Harvard Square. Just a 15-minute subway ride out of the city and you’re standing in the middle of arguably the most prestigious school in the United States. Believe it or not, it’s a serious tourist attraction. If you’re witty enough, you’ll have to make the joke to all your friends back home; “Yeah, I flew through Harvard…that was easy! In one gate and out another!”

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1mi 00h 07m
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2mi 00h 07m
Photo of Boston Public Garden
4.5

4 Charles St, Boston, MA, US

Boston Public Garden

Or maybe you’re a movie buff. Have you ever seen “Good Will Hunting?” Personally, it’s my favorite movie. Much of the film was shot throughout Boston, which is what excited me most about visiting the city. The bench from the park scene (hopefully you know what I’m talking about) is in the Boston Public Garden. Thankfully, they have a map on their website that points you to the exact bench used, because all of the benches there look the same.

No matter what you like, I’m sure Boston’s got somethin’ for ya. It’s very cultural, very lively, very unique. Of all of the big cities I’ve been to, none have felt as welcoming as Boston has. And you just can’t go wrong with great food and great people.

Selena K

Wanderlust seeker & exploring gems the world has to offer.