I am fascinated by urban revitalization and gentrification in the Midwest, and I have written about major Midwestern cities such as Kansas City, Milwaukee and Detroit that are experiencing big changes.
Cleveland is another city to add to the Midwest destination list!
With significant infrastructure investments downtown as well as millennial entrepreneurs returning to the city, Cleveland has been and continues to be in the throes of urban revitalization. I have had the pleasure of visiting Cleveland twice in the last two years for family events, and I make sure to squeeze in a few travel adventures each time!
Cleveland is a city that has a lot of challenges, but the local people have a lot of pride in their city which is palpable from the minute you arrive. As one of the biggest cities in Ohio, Cleveland has plenty of exciting things to explore over a weekend visit, which I have compiled into a 48 hour itinerary!
Day 1
Morning: Rock & Roll Hall of Fame
Perhaps the most famous attraction in Cleveland is the Rock & Roll Hall of Fame. Situated on the shores of Lake Erie, this sprawling museum pays homage to some of the most famous musicians in the world. The museum consists of 4 stories, taking you through the years of rock and roll music all the way from its roots to the contemporary period.
You don’t need to be super knowledgeable or passionate about music to enjoy this museum (I am by NO means a music buff), because the exhibits are very interactive and fun. Don’t miss the concert compilation in the Power of Rock hall — it exceeded my expectations! If you are moving through the museum quickly, it will take about 2 hours to visit. If you are going more slowly, it could take all morning, between 4-6 hours.
When you’re done at the museum, swing by the nearby Slymans for one of the best corned beef sandwiches you’ll ever have. It is cheap and messy and totally worth it.
Early Afternoon: Westside Market
Westside Market is the oldest indoor/outdoor food market in the city, and offers delicious fruit, vegetables and cuisine from more than 100 vendors. It is an adventure for your taste buds as you wander through the stalls, sampling items ranging from cheese and meat to gyros and tacos. Just look at me chowing down on this gyro! If really want to get to know the best of the Westside Market, consider doing a food tour with Taste Cleveland Food Tours which offers a great history and food tour inside the market which will leave you feeling full.
Outside of the market, 25th street has several blocks of unique shops and restaurants to explore within walking distance. You can’t go to Ohio City without a stop at the delightful Mitchell’s Ice Cream, which is only a few blocks north of West Side Market. Save room for sweets! This is their flagship location, so you can watch the ice cream churning while you enjoy delicious flavors such as bing cherry chocolate chunk or campfire s’mores.
Late Afternoon: Shopping in Ohio City
Further south on 25th street, you can find the iconic Greetings from Cleveland mural, which was painted by Victor Ving and Lisa Beggs. This duo specializes in classic postcard letterings, and they are on a 4-year RV trip around the US, with the goal of painting a mural in all 50 states! I fell in love with their work in Chicago, and now I seek out their murals in any cities I go to.
For some local shopping in this area of Cleveland, I highly recommend browsing at Room Service. Merchandised like an independently owned Anthropolgie, this shop had me drooling at all the gorgeous clothing and home decor pieces inside. Only a few shops away, Salty Not Sweet features a diverse assortment of handcrafted gifts from local Ohio makers, ensuring that your dollar stays in the Cleveland economy. A couple more blocks south is the adorable Wild Cactus Boutique which curates a mix of contemporary and vintage items with a Joshua Tree boho flair at excellent prices.
Evening: Tremont Neighborhood
One of the most interesting neighborhoods for food in Cleveland is Tremont, where many famous Ohio chefs have restaurants, including famed Cleveland celebrity chef Michael Symon’s Lolita. Barrio, a continuously expanding local taco chain, or perfectly bubbly pizza and Italian-inspired New American food from Fahrenheit are both great choices for dinner.
If you opt to come to Tremont for breakfast instead, the two most popular spots in the neighborhood are Grumpy’s Cafe, a no-frills diner style breakfast, or Lucky’s, an ever-changing menu of creative takes on brunch classics.
In addition to delicious eateries, Tremont is an artistic neighborhood with street murals and galleries mixed among the Victorian homes. A few galleries worth mentioning are Calicchia Studio and Doubting Thomas Gallery as well as the charming boutiques like women’s wear shop Banyan Tree and Wine & Design, a wine and interior design shop! Don’t miss your chance for a great sunset picture at 1 of the 6 Cleveland Script signs located at 1502 Abbey Ave. Looking for the other 5? The Cleveland Traveler has a great write-up of where you can find all of the Cleveland Script signs (along with some really great local resources for traveling in Cleveland!)
Historically, Tremont was the neighborhood where affluent Clevelanders built their massive Victorian homes, so this is a fun place to walk around and oogle at restored Victorian homes. You might also stumble upon a famous house — the Christmas story house! The home has been converted into a museum dedicated to the movie, so if you’re a big fan, make sure to stop by.
Day 2
Morning: Lake View Cemetery
While it may sound weird to start your second day in Cleveland at a cemetery, trust me when I say the serene location of Lake View Cemetery is truly beautiful with a few fascinating attractions within. The hilly, tree filled area is a popular running area for local students and residents rolling across nearly 300 acres.
Within the cemetery, don’t miss a visit to Wade Memorial Chapel, a small church that was entirely built by Louis Tiffany. Yes, that Tiffany. The walls are clad in a hand-crafted mosaic and the back of the chapel has one of the Tiffany’s most exceptional stained glass murals, valued at over 9 million dollars. Also in the cemetery is the burial site of the 20th president James A. Garfield, which recently underwent a major renovation to restore the elaborate gold mosaics inside the memorial dome.
Early Afternoon: Cleveland Museum of Art
One of the “can’t miss attractions” in Cleveland is the Cleveland Museum of Art. The exquisite collection at this museum ranges from an extensive assortment of Egyptian relics to a fascinating display of medieval armor to modernist pieces from Andy Warhol. There are more than 60,000 pieces at the Cleveland Museum of Art, but they also offer an exciting calendar of rotating exhibits, including (during my visit) a robust collection of Yayoi Kusama’s work. Similar to the Rock and Roll Hall of Fame, you could quickly explore this museum in about 2 hours, but a full visit could take about 4 hours.
Late Afternoon: Detroit Shoreway Boutiques
For your final night in Cleveland, head over to the trendy neighborhood of Detroit Shoreway. Along the way there, spend a few extra minutes driving around the area where you can find many beautiful street art murals! Also, another one of the Cleveland Scripts is located in Edgewater Park if you didn’t get a chance to snap a picture in Tremont.
There are some excellent opportunities for shopping in Detroit Shoreway, especially for handcrafted treasures. Spend your whole paycheck at Fount, a local leather company that makes durable and well-crafted handbags. Find your next favorite pair of earrings or stackable rings at Oceanne Jewelry just across the street which has a metalsmithing workshop inside. For a quirky assortment of vintage furniture, plants and gemstones, peak into Land of Plenty.
Evening: Detroit Shoreway Restaurants
There are several noteworthy restaurants that call this neighborhood home. I lived in Chicago and now Germany, so I know my way around a good wurst, and Happy Dog serves up loaded hotdogs in a variety of unique and fully-loaded options. A few shops down you’ll find the hip Luxe, which dishes up a delicious assortment of high-end Mediterranean and Italian food. Save room for dessert at the charming Sweet Moses, a 1950s-style soda fountain and ice cream parlor.
If you happen to be in this area for breakfast, don’t miss the Cleveland Bagel Company whose housemade bagels are something special. Their flavors are simple but perfect and their cream cheese is SO good. Brewnuts is another good option, which combines cult favorites — beer and donuts. Their instagrammable interior is the perfect backdrop for their extravagant donuts, which range in flavor from Butterfinger to Strawberry Sprinkle, all with the option to add on a pint of your favorite craft beer. 
End your time in Cleveland with a shot of nostalgia at Superelectric Pinball Parlor. I’m not much of a gamer, but my husband loves vintage arcade games, so naturally he wanted to check this place out. The 80s vibe inside will transport you back a few decades with their rows of pinball machines whirring, flashing, and cha-chinging loudly. There are so many more games than I expected, and some have you wondering “How did this game ever get made?” It is clear that the owner has an affinity for famous and obscure games alike!
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