My wife and I were anxious to celebrate our 5 year wedding anniversary in style. Santa Monica? Denver? San Diego? Charlotte? We explored a lot of different options but at the end of the day we decided to be true to our budget and travel a little closer to home.
Yes, my wife and I paid tribute to our five year wedding anniversary with a trip to Cleveland, Ohio. And while that might sound like the start of a bad joke to so many, let me silence your laughter with a wealth of photos that paint a seldom-seen narrative of a mid-sized city that punches far above its weight.

Our first stop was a visit to The Arcade Cleveland, a downtown mall that, like other urban malls, has seen more prosperous days. But the current incarnation as small business and artisan facilitator, as well as reservable event space was great to see. No matter what, this was truly a transcendent display of architecture!



Next, we hopped on the Cleveland RTA Red Line toward the arts and cultural area of the city. And while it was great to see rail transportation options in Cleveland, we were unfortunately very underwhelmed. The Tower City station was difficult to find and navigate, the station was dimly lit and honestly a little scary, the train itself seemed dirty and beat, and the ride itself was fraught with delays. This was one of the few disappointing legs of our stay.


The walk from the train station to the Cleveland Museum of Art introduced us to interesting architecture and iconic street scapes.



The Cleveland Museum of Art was the greatest surprise of the trip. An absolutely stunning lobby greeted us, and the amazing journey grew from there.

I’ve been to the prestigious art museums in Chicago, New York and beyond. This experience was easily on par with their greatest efforts.

The magic just kept going, as meticulously manicured spaces featured brilliant art spanning a multitude of tastes, interests and time periods.





Outside the museum, we stumbled upon a sidewalk chalk festival, where anyone from artist to amateur could buy a square and create a masterpiece.







In the evening, we enjoyed the beautifully-lit downtown, and ended up at the nightlife hub that is East 4th Street. A pedestrian-only stretch of restaurants, bars, shops, and even a bowling alley, the space is yet another example of what a street can be when we combine, walkability, apartments, destinations, and eye-widening visual intrigue. The energy along East 4th Street on a warm fall night was intoxicating… even before we got to the drinks 😉







The next morning, we walked from our downtown hotel to Betts, where we enjoyed a delicious brunch.




As soon as we stepped outside, we were greeted on the street by a person “wearing” a massive yellow python! While neither of us had the guts to handle the giant reptile at the woman’s urging, it was quite an experience to touch and “pet” its massive body. The handler talked about how she liked introducing people to snakes and de-stigmatizing their scary stereotypes.

You might ask why I highlighted this encounter. In cities, we are all more likely to come into contact with people of all walks of life. When you combine high population density with walkability, street performers, interesting individuals, and yes, even snake handlers add to the spontaneous flavor of one’s everyday existence. For example, I realized that this encounter, as brief as it was, sticks out as one of the top 10 things I remember about our short time in Cleveland. The spontaneous encounter added an unexpected moment of adventure to our day, which made our otherwise wonderful trip that much more memorable.
After our reptilian rendezvous, we darted across the street to the Cleveland Trust Building at my wife’s urging. We stepped inside and were immediately overwhelmed by the former bank that was now a magnificent downtown Heinen’s grocery store. I have never in my life been so inspired while shopping for food!




We continued through the city as we made our way north toward Lake Erie. Along the way, the blend of park-like settings and architecture that spanned generations left us in awe.











We stopped into the Cleveland Public Library, which featured an inspiring yet comforting interior.






As an added treat, we stumbled upon an incredible library exhibit titled “The Archive,” in which 500,000 dried flowers hung from on high, creating a breathtaking immersive experience!






After leaving the library, we continued our march toward the waterfront. The mid-September sun was surprisingly intense, and at times the heat got the best of us. But we pressed on, eventually making our way to Lake Erie. Along the way, we passed the famed Rock and Roll Hall of Fame, but decided to leave that for another trip.







In an effort to evade the unseasonable heat, we took an Uber back to our hotel and reset for our next adventure, Progressive Field. A 6-minute walk from our hotel and nestled in the heart of downtown Cleveland, this gorgeous stadium impressed the both of us. I am a die-hard baseball fan, and my wife is a casual-but-knowledgeable enthusiast. Progressive Field appealed equally to both of us!



After a clutch Cleveland Guardians win over the Texas Rangers (who would eventually go on to win the World Series) we headed back to East 4th Street for some late night food and drinks!
After a long rest, we started the our final day at the Cleveland Museum of Natural History, where we saw a variety of animals in a multitude of different environments. Next, we moved on to the nearby Cleveland Botanical Gardens, which featured beautiful natural displays inside and out.













The area around these museums was absolutely breathtaking. Like Central Park in New York and Lincoln Park in Chicago, the feel of nature with the backdrop of urbanity elicited a dreamlike experience.



For the both of us, Cleveland clearly exceeded our expectations. So often we think of our Rust Belt cities with imagery of decaying factories and empty downtowns. This is simply not the case. While these urban centers lost a great deal of population and still need to address many critical issues, they have echos of philanthropic investment, amazing design and sensible connectivity. These are augmented by efforts to re-imagine our downtowns as places where people don’t just want to visit or work, they want to live.
Thank you Cleveland. You made our anniversary memorable 🙂
