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Hipster Travel Guide | Cleveland, OH

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Hipster Travel Guide | Cleveland, OH

A mural of cleveland written in the style of graffiti.

This is your go-to hipster travel guide to  Cleveland, OH. Hipster travel guides are not just for hipsters. They are for anyone who likes to go off the beaten path and live like a local when they visit cities. Here you will find the most happening hood, sights to see, fare to eat, and more!

Nicknames: Greatest Location in the Nation, Forest City, C-Town
Population: 2.25 million in the CLE metro
Happening ‘Hoods: Tremont, Ohio City, Lakewood
Locked in loving embrace by the southern shore of Lake Erie sits a city that boasts “progress and prosperity†second only to its rocking roots. This fertile land of northeast Ohio has been called home to protopunk bands Pere Ubu, Dead Boys, and Electric Eels, plus melodic masters Bone Thugs-n-Harmony. C-Town has also served as a backdrop to Harvey Pekar’s American Splendor and, most notably, The Drew Carey Show. This city is no “mistake on the lake,†despite what you may have heard; The MidWasteland truly believes the C stands for charm and we’ll tell you why in this hipster travel guide to Cleveland.


Each year around the middle of July, downtown Cleveland opens its arms to hundreds of creators celebrating innovation in technology and art. Sprawled out across the Theater District, inside unused storefronts and 1,000-seat auditoriums, Ingenuity Fest welcomes both international and local participants alike. So take part in the spectacle or watch it from afar – weekend passes are ridiculously cheap at $15!
Also throughout the summer, individual street festivals flare up in every corner of the city. The historic Hessler Street Fair, first started as a means of neighborhood preservation in 1969, unofficially kicks off the summer season. From Hessler Street head west down Murray Hill straight into the heart of Little Italy. The narrow brick-paved hill, packed from side to side with galleries, bakeries, and authentic Italian cooking, is home to a slew of summer festivals, most notably The Feast Of the Assumption. But if large crowds and cannoli aren’t you’re thing, stop back to Murray Hill for its series of Art Walks, which take place the first weekends of June, October, and December.


The man known as Moondog, WJW Radio DJ Alan Freed, was responsible for coining the term “Rock and Roll,†so it might be looked at as some sort of sin to pass up a day perusing the precious artifacts at The Rock and Roll Hall of Fame. The building, designed by I.M. Pei (the designer known for the Louvre’s famed glass pyramid in Paris), sits nestled up against the lake just east of downtown.
If you’re looking for neoclassical architecture, the downtown skyline may be small in size but it packs enough Beaux-Arts punch to make Walter Gropius roll over in his grave. Catch a glimpse of the glistening lakefront from three grassy parks amidst the postmodern metropolis, constructed by internationally renowned architect Daniel Burnham. For an even greener view, take a hike through the Emerald Necklace, Cleveland’s four urban parks connected through the city. Or — in a stretch of land no longer than a mile — get acquainted with the varying ethnicities that make up the city by way of the Rockefeller Park Cultural Gardens.
Once you’ve finished hiking, take the Shoreway straight to the west side, and don’t forget snap some pix of yourself in front of the St. Theodosius Russian Orthodox Cathedral in Tremont, which once served as a backdrop in the wedding scene of Deerhunter. Head east to Lake View Cemetery, where the burial grounds of James A. Garfield and John D. Rockefeller are second in coolness only to the pond containing the scattered ashes of former police chief, and “Untouchable,” Elliot Ness.


From Chef Boyardee to a broad range of kindly local (read: Midwestern) chefs, Cleveland can’t help but satisfy any girl’s deep down longing for comfort food. First stop: Melt Bar and Grilled. This shop serves any kind of grilled melty cheese-on-bread you can ask for, plus fresh soups and salads. But if your most comforting sandwich involves a ground beef patty, try the choice burgers at the cutest little brick-storefront shop, Heck’s, in the Ohio City ‘hood.
Dessert in C-Town is also extra cozy and cute, whether you’re sampling a requisite cannoli at Corbo’s Dolceria in Little Italy or licking an ice cream cone at Honey Hut. If nutritional treats like all-fruit smoothies are your thing, try the Algebra Tea House; modeled after an old schoolhouse, this place is quite possibly the most charming spot of all. But if your pockets are pinched from a long day of sight-seeing, get more bang-for-your-buck at The West Side Market, Cleveland’s oldest locally-owned market, where you can feast your eyes on roughly 100 vendors’ hand-produced or hand-picked goodies.
Finally, make sure you save an afternoon for beverage therapy. If you thought beer was only brewing in the fictitious garage of Drew Carey, head over the Bob Hope Bridge to the west side for a tour of Great Lakes Brewing Company and find out just how they make those sweet and succulent environmentally-conscious beers.


The sun may go down on this once-sleepy town, but the rock never ceases to stop. Just east of downtown sits a strip of land formerly known solely for its maddening population of Hippies. Coventry Road is no stranger to change, so if you happen to find yourself meandering through crowds of frat boys on their way to the next sports bar, fear not; a handful of classic Coventry establishments are still afloat. Follow the stretch south until you hit the corner, and stop when you see The Grog Shop. The cheap beer never stops flowing at this rock relic, unless of course you’re under 21 — in which case a grey-haired fellow, notorious for spotting X-marked hands, will hunt you down like a hawk and kick you out.
If you’re out and about on the east side in Collinwood, you’re just steps away from the renowned Beachland Ballroom and Tavern. Don’t let the name fool you, it’s not as swanky as it sounds — in fact, the two venues are arguably the coziest in town. But if you feel too far from the action in the ballroom, or too intimately placed in the tavern, follow the arrow saying “This Way Out.” You’ll find yourself miraculously among a few small racks of specially-selected vintage clothing and accessories. This place has it all.
Film buffs, you’ll be happy to know that Cleveland has a place for you, too. The Cedar Lee and Shaker Square Cinema are two of the best spots to catch a good art flick — in fact, they’re the only two. Yes, art house tickets are a bit pricier, but with half-priced happy hour drinks and five-dollar bargain Monday deals, these priceless commodities are sure to make you love every minute at the movies.


Cheap rent means one thing for thrifty Clevelanders: cheap vintage. From Flower Child to Suite Lorain, warehouses and rehabbed bowling alleys are stocked to maximum capacity with Peter Pan collars, poor boy hats, petticoats, you name it. Just be sure to set aside at least four three to four hours to sift through the endless racks, because you’ll be hard-pressed to find more reasonable, reliable vintage garments.
If you’re out by the Beachland before a show, make sure to pop in and check out the latest releases at Music Saves. On the right night, you just might catch a stripped-down set with whoever is on the bill next door. If you’ve got all the music you need, ask co-owners Melanie or Kevin where you can find the buzz-worthy designs from Cleveland’s hottest entrepreneur of the moment, Kristen Billings. Buzz Buzz Designs might not have its own store yet, but considering Cleveland’s love of the co-op, you’ll be sure to find some of her recycled vintage pieces while perusing through the gallery scene.

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