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Exploring Cleveland’s Hipster Hotspots & Coolest Neighborhoods

At the end of last summer I planned a short trip to Ohio during my Hipster America Project. The plan was to visit family, but also to explore two cities I hadn’t ever explored before: Cleveland and Columbus. By the end of my one-week trip, I was pretty surprised to find both cities actually quite interesting.

Cleveland’s history with rock & roll is quite famous, but these days it doesn’t seem to attract the same appeal. So I set out to discover the cool side of Cleveland’s unique neighborhoods on my short weekend trip. Here’s what I found…

A Guide to Cleveland’s Coolest Neighborhoods

tremont farmers market
Farmers’ Market in Tremont

Tremont—Cleveland’s newest hipster neighborhood

My first night in Cleveland started off with a quick visit to the Tremont neighborhood—a scenic part of Cleveland’s outskirts that was once part of a different city before being annexed to Cleveland in the 1850s.

In the 20th century, the neighborhood was mostly made up of Eastern European immigrants (most notably from Poland) and today, with the influx of artists, hipsters and gentrifiers, it’s generally regarded as an up-and-coming hotspot for locals.

With farmers markets, art fairs and ethnic restaurants, Tremont is definitely the hip place to be these days in Cleveland. I walked around on a brisk, cool summer evening taking some photos and seeing what the neighborhood had to offer.

The buildings were pretty (many have been restored in recent years) and the atmosphere was cozy. Lincoln Park is pretty much the historic center of Tremont and I stumbled on their farmers’ market. Plenty of art galleries and artist studios are on the streets around Lincoln Park. And for those especially ambitious tourists and movie fans, the famous Christmas Story house is located in Tremont.

prosperity social club
Prosperity Social Club

For dinner I went to the highly recommended Prosperity Social Club (@ProsperitySC) in Tremont. It’s not a real social club in the historical sense, but definitely evokes the same kind of atmosphere. With a tastefully kitsch design (there’s an arcade bowling machine!) and a retro style throughout, it was the perfect ambiance for a casual, unpretentious dinner.

While sitting outside in the backyard beer garden, I sampled several of their appetizers—from pierogi to empanadas—and washed it all down with a few craft beers. You could definitely tell that this was the type of place for locals, popular even on a weekday evening.

cleveland restaurant
Dinner at Prosperity Social Club in the back garden: empanadas
Arcade bowling inside the Prosperity Social Club
nanonbrew bar
Nanobrew – Cleveland microbrewery

A Night Out in Owl City (best neighborhood for nightlife)

After enjoying Prosperity Social Club’s beer garden, I decided to check out Cleveland’s other hip & trendy neighborhood: Ohio City. Historically its own city (briefly), today the area is designated “Cleveland’s Artisan Neighborhood.” The area is definitely hip with craft beer bars, nightlife, galleries, restaurants and even Cleveland’s very first hostel.

During my night out in Owl City, I went for a beer at the new Nano Brew (@nanobrewcl) which offers 24 different beers on tap. The Nano Brew bar and restaurant sits on a street corner and the bar’s outdoor patio has a nice view of the Cleveland skyline off in the distance.

The bar’s logo and style definitely evoke a hipster theme, but like the Prosperity Social Club, it’s relatively unpretentious.

menage a trois brunch
Latitude 41ºN for brunch

Hearty Brunch at Latitude 41°N

After a night out of drinking Cleveland’s own local beers (don’t ask me which ones, though), I started my next morning with a big cup of *unlimited* coffee at Latitude 41°N. The restaurant is famous for their homestyle country food and their BIG brunches.

Located in the Gordon Arts district (one of Cleveland’s coolest neighborhoods), I started my morning off with their legendary Ménage à trois brunch special: eggs, toast, bacon, sausage, potatoes and unlimited Columbian coffee. I added some fried tomatoes and a quesadilla to make it extra hearty. Delicious!

brunch in cleveland
Legendary Menage A Trois brunch special at Latitude 41ºN
capitol theater
Cleveland’s indie movie theather: the Capitol

Exploring the Gordon Square Arts District (best neighborhood for art & creativity)

After my leisurely weekday brunch, I did a bit of exploring through Cleveland’s Gordon Square Arts District (@gordonsquare). Another hipstery neighborhood, the main drag is along Detroit Street between 58th and 67th streets.

With a few streets worth of independent galleries and shops, the area is definitely on the rise. The historic Capitol Theater regularly shows indie movies as well as foreign movies and documentaries, but all I saw was their retro signage.

Walking along the main street I spotted a handful of bars, restaurants and indie shops. Nothing much was open on a weekday afternoon, but on weekends and evenings I’m sure the place is buzzing with Cleveland’s hipsters.

cleveland shop
Yellowcake boutique shop in the Gordon Square Arts District
sweet moses
Sweet Moses Soda Fountain & Sweets Shop
street art cleveland
Across from the West Side Market in Cleveland

Exploring Ohio City During The Day

Though I spent an evening out in Ohio City the night before, I went back to the arts district to discover what else I could find. One of Cleveland’s more popular tourist destinations is the West Side Market, Cleveland’s oldest food market.

Today the main hall is a great place to grab lunch or just enjoy some good old-fashioned people-watching. I spotted kiosks and stands selling everything from pierogies to gyros for lunch, in addition to the typical fresh fruits, veggies & meats.

One of the stands, Steve’s Gyros, was even featured on a Man vs Food episode. If you go, there’s a stairwell off near the bathrooms which you can climb up to get a birds-eye view of market.

west side market
Birds-eye view of the West Side Market
glass blowing
Glass Bubble Project

Around the corner from the West Side Market are many of the craft beer pubs (where I did some nighttime exploring), but there were also galleries and small shops on the surrounding streets. There’s even a studio which offers glassblowing classes—something I did last year in my hometown.

rock & roll hall of fame
Rock & Roll Hall of Fame

Downtown Cleveland—A Neighborhood for Public Art

After spending most of my days exploring the outlying neighborhoods of Cleveland, I eventually decided it was time to see what downtown Cleveland had to offer. I spent a few hours inside the Rock & Roll Museum before setting out on a walk through the city center. While it was pretty quiet and there weren’t many people around, it was still a nice day for some urban exploration.

I stumbled on one of Cleveland’s more famous public art pieces: the Free Stamp. Bit bizarre but the piece (sometimes called the world’s largest rubber stamp) is definitely a quirky attraction worth seeing.

Wandering around downtown Cleveland I also stumbled on some street art (“Life is sharing the same park bench”) and a weekly food truck festival (Walnut Wednesdays)—the city is clearly one of great art.

public art
Free Stamp created by Claes Oldenburg and Coosje van Bruggen in Willard Park
street art
Downtown street art
nosh box food truck
Walnut Wednesdays food truck festival
At Walnut Wednesdays, we weren’t the only ones looking for food…
Melt bar & grilled
Melt Bar & Grilled — grilled cheese sandwiches

Where to Eat in Cleveland

Continuing with my theme of eating ethnic foods in Cleveland, I decided to end my trip at one of the city’s more popular restaurants: Melt Bar & Grilled. The super-American restaurant/bar basically serves one type of meal, but with lots of variations. Grilled cheese.

Can’t get much more American than that! I tried the grilled cheese sandwich with pierogi inside, and @dangerousbiz who joined me for dinner had an Italian version with meatballs.

The sandwiches were massive and I’m glad I ate there…but I don’t know if I could do it a second time. This Cleveland restaurant was also featured on Man v. FoodSeems that Adam Richman and I have something in common: an interest in Cleveland’s food scene!

Cleveland—more hip than I first imagined

After spending a few days in Cleveland, I’ve definitely determined that the city is way more cool than I first guessed. Before visiting, I assumed the Rock & Roll Museum would be just about the only thing to keep my interest, but getting the chance to explore the Ohio City, Tremont and Gordon Square neighborhoods, I quickly realized there was a lot more to the city.

Cleveland’s coolest neighborhoods have art, culture, amazing food, and plenty to keep you entertained for a weekend trip.

It’s particularly a good city to visit for fans of food, beer and typical Americana. After all, Cleveland is in America’s heartland.

  1. Love this! I’m headed to Cleveland for the 25th time next month (I have tons of family and friends there) and will have to check out some of these suggestions! I’ve always found the city surprisingly hip.

    • Adam says:

      25 times?! That’s impressive Lillie! “Surprising” is probably the word I’ve used the most to describe Cleveland. No one I know who’s been has been bored!

  2. i’ve yet to get to cleveland, but everyone says how great it is – i can’t wait! i esp can’t wait for the west side market – YUM!!!

    • Adam says:

      Thanks for commenting! Yeah, Cleveland is a surprisingly hip city — great for a short trip!

  3. Sarah says:

    Cleveland native living in Melbourne, Australia here! I often try to sell Cleveland’s merits to my overseas friends and this is the perfect proof! Thanks for highlighting CleveLAND that I love!

    • Adam says:

      Hey Sarah, Glad to see a Clevelander so proud of her hometown! From the other people I’ve met from there, it seems everyone’s got a bit of pride which is just great.

      Melbourne is a great city, too!

  4. Cat of Sunshine and Siestas says:

    Well, you’ve done it: Cleveland is now on my radar! I love when Midwestern cities are sure to disappoint and then end up be surprisingly fun. This, from a Midwesterner!

  5. Micki says:

    Oh, my gosh I love the Melt Bar & Grilled. I may just have to head to Cleveland to try that out.

  6. I would not have pegged any of these places as being in Cleveland. Great finds…

  7. When I hear of Cleveland I automatically think of Hot in Cleveland :) I’m not sure if you heard of this sitcom…

  8. Brian says:

    Although I’m glad you liked Cleveland, I think “surprising” is a bad way to think about it. Anyone who’s known anything about the city has known for a long time what we have. I mean, the West Side Market is now 101 years old. A lot of this stuff isn’t new, it’s just that no one cares about cities that aren’t on the coasts. From my experience, Cleveland has more to offer than most other cities. Mostly because it’s a “real” place. It’s not just good for a weekend visit, but also for life!

  9. Mike says:

    I moved back to Cleveland from Chicago for many of the reasons you experienced on your trip. The food is great, the beers are great and the people are generally nice to everyone willing to explore their city (being a stranger in Cleveland means you aren’t willing to talk to people). It has been a year since I moved and I have no regrets. There are also a ton of new experiences happening everyday that I have yet to explore. North Coast Comeback!!!

  10. tina says:

    I’m glad you enjoyed your time in our awesome city! I’m a glass blower at the Glass Bubble Project. Did you get to meet our rooster?

  11. Jan Rodems says:

    I hope you can enjoy another trip and all the North Coast offers….the lake is amazing.

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  13. TH says:

    You missed likely one of the best stops in Cleveland, University Circle with The Cleveland Museum of Art – The Cleveland Institute of Art Cinematheque – and other great spots including MOCA, the French Bistro L’Albatros, ABC Tavern, Cleveland Botanical Gardens, Western Reserve Museum, and a rejuvenated Uptown district. Come back and see!

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