Caroline in the City Guide to Cleveland

Settled on Lake Erie and the Cuyahoga River, Cleveland, Ohio was established in 1796 by General Moses Cleaveland, for who it is named. The creation of the Ohio and Erie Canal sped up development as immigrants moved from Hungary, Poland, Italy, and beyond. Cleveland also became an important place for The Underground Railroad.

In modern times, the city is known for its connection to music history, considered to be the home of rock and roll. It’s also home to a number of sports teams, including the MLB’s Cleveland Guardians, the NFL’s Cleveland Browns, and the NBA’s Cleveland Cavaliers. The Midwestern city is a charming weekend getaway for fans of craft cocktails, architecture, and culture.

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The Neighborhoods of Cleveland

Most visitors to Cleveland stay downtown and miss out on the incredible neighborhoods that make it so unique. You don’t have to go far to see some of the best ones.

Centered around Gordon Square, this area was first home to a shipping canal. Detroit-Shoreway is a bustling arts district with restaurants, bars, and shops. The Capitol Theatre plays first-run movies and the Cleveland Public Theatre has performances throughout the year.

Located west of the Cuyahoga River, Ohio City was home to the city’s most famous names, like John Heisman, and the famous landmarks, like the West Side Market. These days, you’ll find a sprawling urban farm and many craft breweries. There’s also an art museum and an original Carnegie library, still in operation.

Lakewood was established in 1889 as one of the city’s streetcar suburbs, set west of downtown. Within it are even more smaller neighborhoods like Birdtown, Clifton Park, and Victorian Village. Here visitors can tour a craft distillery or see religious relics at The Sanctuary Museum.

Little Italy is one of the oldest parts of Cleveland, set near the campus of Case Western Reserve University. Established in the 19th century, Mayfield Road is lined with shops, Italian restaurants, and bakeries selling cannolis and other treats. Visit with a local on the Little Italy Neighborhood Food Tour of Cleveland.

Follow the popular Towpath Trail to the Tremont neighborhood, snapping a photo at the famous Cleveland sign. Here visitors can experience quirky museums, like the Christmas Story House, or explore Lincoln Park. There are a number of unique cocktail bars, like the famous Spotted Owl, and restaurants. Explore the best with the Tremont Neighborhood Food Tour.

Cleveland Restaurants and Cafes

The best part about visiting Cleveland is the many locals that will offer up suggestions on places to eat and you can’t go wrong with just about any of them. The international dining is especially unique, as the city is home to Italian, Polish, and Hungarian communities dating back generations. Looking for even more restaurant suggestions? My friend Amanda at Cleveland Traveler has plenty!

27 Club– This trendy coffee shop is owned by Cleveland native Machine Gun Kelly and is themed around musicians that tragically died young. Come for quirky coffee drinks, sandwiches made to order, and pizza. By night, they serve cocktails and beer.

Brewnuts– The Detroit Shoreway area bakery is known for its over-the-top doughnuts, which often sell out. The flavors change weekly, so you never know what you might get, but the sizes of the doughnuts, which are made with beer, are generous.

Cleveland Bagel Company– The bakery popularized the “Cleveland bagel” with a number of varieties including the popular rosemary sea salt. There are two locations but be prepared to wait and enjoy your meal on the go as there’s no dine-in currently.

Collision Bend Brewing Company– Set in a 1863 building on the water, this brewpub has the perfect summertime patio to enjoy a house-made beer. The food is excellent as well, including flatbreads and the honey hot sauce fried chicken sandwich.

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The Flying Fig– This restaurant near the West Side Market focuses on farm-to-table dishes with ingredients sourced locally. Enjoy dishes like braised Ohio beef, Walleye with honey nut squash, and pappardelle pasta with lamb shank and jus.

Guarino’s Restaurant– Considered to be Cleveland’s oldest restaurant, this cozy Italian restaurant has been a Little Italy staple since 1898. Dine on favorites like prosciutto stuffed olives, gnocchi in pesto, and veal marsala. Finish your meal with an espresso and tiramisu.

Immigrant Son Brewery– This new Lakewood brewpub makes its own beer in-house and has a menu of Hungarian-inspired dishes to honor the owner’s mother. Be sure to order the Hungarian burger, made with langos, a Hungarian flatbread.

Larder Delicatessen and Bakery– The former Hingetown firehouse has twice been nominated for the James Beard awards. The cozy space has a menu that changes daily, but includes hearty sandwiches and soups, along with prepared foods and groceries to take home.

Prosperity Social Club– The 1938 bar has a new generation of fans for its welcoming atmosphere and live music. The menu includes European dishes like pierogis, kielbasa and cabbage, and even vegan burgers. There are weekly events like fried chicken Sunday and fish fry Friday as well.

Cleveland Bars and Nightlife

Like any good Midwestern city, Cleveland has an excellent drinking scene. Craft beer? Absolutely. Funky dive bars with bowling and other games? Definitely. Refined cocktail bars that have a list of ingredients you can’t pronounce? For sure.

Cloak and Dagger– Be sure to make reservations for this Tremont cocktail lounge that changes its cocktail menu based around the season. Each drink is creatively concocted and there are low-proof or spirit-free versions as well. They also have vegan sandwiches and snacks.

The Fairmount– The neighborhood bar in Cleveland Heights makes its own ginger beer, which goes into drinks like the Moscow Mule. The menu also includes cocktails to share, along with flatbreads, burgers, tacos, and vegan dishes.

Flight Cleveland– If you’re in the mood for wine, go to the experts at this wine shop and bar. If you’re still making up your mind, the team can pour samples of any of their wines and can make recommendations based on your preferences and tastes.

Forest City Shuffleboard– For drinks with a side of fun, this shuffleboard and arcade bar is the best place for it. Chow down on burgers, sandwiches, and loaded tots with your barrel-aged cocktails and buckets of local craft beer.

Great Lakes Brewing Company– This employee-owned microbrewery has a large presence in Cleveland. Visitors can dine at the brewpub before going on one of the free tours of the brewing operation.

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Market Garden Brewery– Located next door to the West Side Market under a large neon sign, this award-winning brewery has beer and dishes inspired by Cleveland. This includes German-style pilsners and hefeweizens, West Coast-style IPAs, and dry cider.

Porco Lounge and Tiki Bar– The tropical wonderland is in an unassuming building in an industrial part of Tremont. Polynesian-inspired drinks like mai tais and painkillers are the main draw as well as shared drinks like the scorpion bowl.

Saucy Brew Works– With a few locations in town, this sports bar brews its own beer including IPAs, kolschs, and stouts. If you’re getting hungry, they also have pizza, including with vegan cheese.

The Spotted Owl– The highly praised cocktail bar lets visitors choose their own adventure by selecting a flavor profile for the bartenders to create something unique. So you might have a different experience each time. There’s a location in Tremont and another in Akron.

Superelectric Pinball Parlor– A $6 fee will cover all you can play pinball games, including themed versions from Stranger Things and Star Wars. You can also enjoy a local craft beer or cocktail between rounds and the machines even have cupholders for easy playing!

Western Reserve Distillers– The family-run craft distillery in Lakewood uses only the finest organic ingredients in their spirits, including tequila-style agave spirit, bourbon, gin, rum, and vodka. Grab a cocktail made with the spirits, along with a full restaurant menu.

Want to check out Cleveland’s best breweries? Book a spot on the Sip of Cleveland Brew Tour. Thrillist also has a list of the city’s best bars.

Things to Do in Cleveland

There’s plenty of things to do, but without a doubt, there’s one museum that brings in visitors from around the globe. But check out the quirky and lesser-known attractions as well as the incredible architecture that can be found around every corner.

A Christmas Story House Museum– The house used in the classic film has been restored and is open for tours. The space is stocked with replica props and set pieces. There’s also an adjacent museum with costumes from the film as well as vintage cars used in the production.

Cleveland History Center– This museum tells the story of the city’s history, with exhibits on the Shaker religion, paintings and artwork, and vintage automobiles. Get your Cleveland History Center Admission Ticket before you go.

Cleveland Museum of Art– Expect to spend a few hours roaming the galleries at this incredible museum founded in 1916, which is free to visit. It holds over 45,000 pieces from Africa to India, along with special exhibits. It even rivals the Art Institute of Chicago!

Edgewater Park– A beach in Ohio? That’s right! This local park has a public beach where you might spot surfers, along with a pavilion for performances, a fishing pier, and dog-friendly areas.

Rock and Roll Hall of Fame– If you only make it to one museum, make it this one. Spread across seven floors in a pyramid-shaped building, there are interactive exhibits and artifacts on every major musician for the last fifty-plus years. Get your Rock and Roll Hall of Fame Admission before you go.

The Transformer Station– The small building in a 1924 railroad substation has a rotating collection of contemporary art. It’s also free to visit and hosts workshops and classes.

Shopping in Cleveland

Pick up unique souvenirs for yourself around the city from the local boutiques, all selling the best items showcasing their city pride. But if you’re looking for retail giants, you’ll find them as well. 

The Arcade– Don’t miss this beautiful Victorian shopping arcade built in 1890 that is attached to the Hyatt hotel. It has eight restaurants, along with shops selling tea, artwork, and more.

Fount Leather– This stunning boutique sells locally made leather goods including handbags and wallets.

Himiko’s Cool World– The colorful and nostalgic store sells everything you could want from vintage clothing to handmade jewelry to funky home decor.

Oceanne Studio and Boutique– Shop for French-made minimalist jewelry along with cards and other gifts at this light-filled store.

West Side Market– Built in 1912, the indoor and outdoor market has dozens of booths selling cheese, bread, meat, and prepared foods. Visit with an expert guide on the West Side Market Food Tour to avoid being overwhelmed with options.

Looking for even more shopping in Cleveland? Cleveland Magazine has a list of its favorite stores.

Where to Stay in Cleveland

Cleveland’s hotels are mainly clustered around downtown and many are in historic buildings that have been preserved. Also check out rentals like Airbnb, which can be found in the local neighborhoods.

The Cleveland Hostel– Staying in Cleveland doesn’t have to break the bank! The city has an independent hostel, which welcomes budget-minded travelers with private and shared rooms, a guest kitchen, free parking, and free WiFi.

Kimpton Schofield Hotel– The 122 room boutique hotel in a historic building has everything to love from the Kimpton brand including free coffee and tea and daily happy hour. There’s also an in-house restaurant, in-room yoga mats, and stylish rooms.

Metropolitan at the 9– Another historic building-turned-hotel is just down the street from the Kimpton. The Metropolitan has an Art-Deco atmosphere with two restaurants, a rooftop bar, a fitness center, and WiFi.

Hotel Indigo Cleveland Downtown– This pet-friendly hotel has its own restaurant, a fitness center, and free WiFi.

Airbnb– Get the local experience by staying with one. There are rental options all over the city, so look for ones in Tremont, Ohio City, and Detroit-Shoreway.

Transportation in Cleveland

When arriving at the Cleveland airport, you have a few options for getting into the city. You can book a rideshare or a private transfer, which should take between 20 and 30 minutes, depending on where you’re staying. There’s also an RTA train directly into the city center, which costs $2.50 each way.

If you’re arriving on Amtrak, the train station is one block away from the Rock and Roll Hall of Fame. The Capitol Limited and Lake Shore Limited make stops in the city. In terms of buses, Greyhound and Megabus arrive at the Stephanie Tubbs Jones Transit Center downtown.

The RTA runs trains all over the city on four lines, along with buses, including to Little Italy and Lakewood. If you’d rather walk, Cleveland is a very easy city to get around, despite its size. Much of downtown can be explored on foot but be sure to wear the right shoes.

Uber and Lyft both operate in the city, which is ideal for getting home at night or those early morning airport runs. Get a discount on your first Lyft ride by using the code “CAROLINE868074”. There are also scooters, including Bird and Lime.

Cleveland Tourism assisted in the research of this guide.