Cleveland

Last year my grandma mentioned that it had been a while since we had traveled together. Admittedly, between Alison being pregnant and then having a baby, we hadn’t gone anywhere with them for a couple of years. Now that Madeline was a little older and we had a lot more experience traveling with a toddler, it felt like the right time to plan a trip.

As we kicked around ideas, we decided a baseball trip made a lot of sense. We narrowed our options to two cities with stadiums we hadn’t visited yet: Cleveland and Pittsburgh. 

When we realized the Yankees would be in Cleveland during the week we wanted to travel, the itinerary practically built itself.

We left on Monday afternoon. My grandparents picked us up and we headed to the airport. We gave ourselves plenty of time, but between checking bags, getting through security, and grabbing some dinner, we still arrived at the gate just as boarding was starting. In fact, they were already preboarding by the time we got there, so we walked right onto the plane.

The flight itself was uneventful, if a little bumpy. We landed a few minutes early. As always, Madeline did great. She was a little loopy by the end because it was well past her bedtime, but she stubbornly refused to sleep. Instead she watched shows, played with her toys, and charmed the people around us. This flight was number 30 for her, which still feels a little crazy to say.

We landed in Cleveland and gathered our bags. Madeline fell asleep while we were waiting at baggage claim. The rest of the crew waited at the airport while I took the shuttle to pick up the rental car. Then I circled back and picked everyone up. We transferred our sleeping baby into the car and headed to the Hilton Garden Inn Cleveland Downtown. Once we arrived, we somehow managed to transfer her straight into her pack and play without waking her up. At that point it was around 12:30 a.m. and after a long travel day we were more than ready to call it a night.

The next morning Madeline slept until about 8 a.m. At that point I got up with her while Alison caught a little more sleep. Mads and I joined my grandparents downstairs for breakfast. We grabbed Alison some food and coffee to go and then got ready for our first activity of the trip.

That activity was the Rock & Roll Hall of Fame. It is one of Cleveland’s signature attractions and sits right on the shore of Lake Erie. By some stroke of luck we found a handicap parking spot close to the entrance. Even still, this wasn’t the easiest stop for my grandpa. He isn’t as mobile as he used to be, and I was a little surprised he decided to come.

He made it about halfway through the first exhibit before deciding to find a place to sit and relax while we explored the rest of the museum. It worked out alright. Traveling with my grandpa has its challenges. He turns 85 this year and it feels like every time we go somewhere, the goalposts move a little bit on what he’s able to do comfortably. We are just glad he’s here and still willing to come along. He’s a trooper.

My grandma, Alison, and I continued exploring. My grandma was very pleased that Madeline’s favorite exhibit was the one dedicated to the Beatles. She also spent part of the morning regaling Alison with stories from her younger days when she loved rock and roll and partied a little more than she does these days. It is always fun hearing stories from parts of her life that I never knew.

Madeline loved all the music. There was also a special exhibit about the music of Saturday Night Live that was really well done. Eventually we made our way to the upper floors and worked our way back down through the museum.

On the fifth floor there was a Pink Floyd wall with a giant monster peeking over the top. Madeline was not convinced it was friendly and repeatedly informed us that it was a scary monster. On that same floor there were stations where visitors could create their own beats. Madeline loved pushing the buttons and putting together her own little musical creations.

We also spent some time in the Hall of Fame section of the museum. We walked through the various induction years pointing out our favorite artists and bands. Madeline enjoyed listening and occasionally pointing out someone as well.

Once we wrapped up at the Rock & Roll Hall of Fame, it was time for lunch. We headed to Mabel’s BBQ, one of Cleveland’s most famous restaurants. It is located right in the heart of downtown and specializes in Cleveland-style barbecue.

Alison, Mads, and I ordered a family-style platter with brisket, kielbasa, potato salad, and baked beans. It also came with pickles, rye bread, and sauerkraut. Everything was very good, but the kielbasa was the standout. It was packed with flavor and was an authentic Cleveland dish.

After lunch we took my grandparents back to the hotel so they could rest for a bit. Then we headed out on a walk. My grandparents needed a few things from the grocery store, so we volunteered to pick them up.

As it turns out, one of the most beautiful grocery stores I have ever seen was located just a few blocks from our hotel. Heinen’s is housed inside the historic Cleveland Trust building beneath a massive Tiffany stained-glass dome. It is absolutely stunning. Underneath all that beauty it is still a normal grocery store, but it might be the most elegant place I have ever bought groceries. They also had a little ice cream cart, so we stopped for a treat. Madeline slept through that portion of the adventure, which was probably for the best.

After grabbing the groceries, we continued our walk and circled Progressive Field. Our hotel was right around the corner, but it was still about a quarter-mile walk from the gate. That is a bit of a hike for my grandpa, but after scouting things out there really wasn’t a better option.

Later that afternoon we met up with my grandparents and made the walk over to the game together. While it was a bit of a trek for Grandpa, he did great. It helped that as soon as we entered the stadium we could check Madeline’s stroller and borrow a wheelchair for him. We were seated on the field level in the second-to-last row, which meant only two steps down to our seats. That was a very intentional choice. The seats were fantastic. They had a great view of the field and were very accessible.

While my grandparents settled in, Alison, Mads, and I took a lap around the main concourse. Progressive Field is a really nice ballpark with great sightlines throughout. We found some popcorn and water to bring back to our seats because Madeline absolutely loves popcorn.

We settled in for Yankees versus Guardians. Gerrit Cole was pitching and we were excited to see him. He had only been back for about a month after missing all of 2025 and the beginning of 2026 following Tommy John surgery.

The Yankees struck first. In the second inning Jazz Chisholm walked and Spencer Jones, who had recently been called up after Aaron Judge’s broken rib, launched a monster home run to make it 2-0 Yankees. It was the first home run of Jones’ major league career and it was a thing of beauty.

Unfortunately, Cole didn’t really have it. In the bottom of the third inning José Ramírez manufactured a run. He singled, stole second, and scored on another single. We hated to see the run, but it was fun to see how fast he was on the bases. Then things unraveled a bit. Cole walked a batter, hit another, and then failed to cover first base on a routine play. I immediately had flashbacks to the worst moment of the 2024 World Series. Before long the game was tied 2-2. Cole escaped the inning, but only made it through four innings total.

By this point Madeline was getting a little restless. It had been a long day. Alison took her for a walk around the stadium.

They met Slider, the Guardians mascot, and Madeline was thrilled. She loves meeting mascots. They also found a sign advertising the kids club. Alison asked an employee about it, and they enthusiastically told her to take Madeline over there.

When they found it, Madeline was in heaven.

There were slides, toys, and all kinds of activities. They stayed there for a few innings while Alison kept one eye on the game and one eye on Madeline. 

They took breaks for the mascot race, which Madeline was surprisingly unimpressed by, and of course for Take Me Out to the Ballgame during the 7th inning stretch. 

One of the more memorable moments of the game came in the eighth inning when Cleveland brought in reliever Matt Festa. His entrance song is Por Ti Volaré by Andrea Bocelli. Festa is Italian and the entire experience was incredible. The song blasted through the stadium while thousands of Cleveland fans stood, sang, and danced along. It felt oddly emotional and almost spiritual. It is one of those uniquely baseball moments that you don’t expect but sticks with you.

Back in our section, my grandparents and I were on the edge of our seats. The Yankees had leaned heavily on the bullpen and the game remained tied entering the eighth inning.

Jazz Chisholm came to the plate and quickly fell behind 0-2. He battled back to a full count before getting a hanging pitch that he crushed into the seats.

3-2 Yankees.

The Guardians threatened in the bottom of the inning with runners on first and second and José Ramírez coming to the plate, but the Yankees escaped the jam. The bullpen slammed the door and New York held on for the win.

I especially loved the bottom of the ninth when Yankees fans throughout the stadium started chanting “Let’s Go Yankees.” Yankees fans travel exceptionally well.

After the game we made the short walk back to the hotel. It is only about five minutes, but Madeline fell asleep on the way. Alison and I were still buzzing from the game, so we stayed up talking baseball before eventually deciding we should probably get some sleep too.

On Wednesday morning we skipped the hotel breakfast and went looking for something local. The first place we tried had a line out the door, so we pivoted and ended up at Rowley’s Inn.

It was excellent.

I ordered a very Cleveland breakfast called the Rogi Omelet. It was stuffed with spicy Hungarian kielbasa, cheddar, sautéed onions, and two pierogi, then served with Cleveland kraut, home fries, and sour cream. It was outstanding. Madeline ordered a giant stack of pancakes and absolutely demolished them.

Right across the street from Rowley’s is the house from A Christmas Story, so naturally we stopped for a few pictures before heading back to the hotel.

We squeezed in a quick nap before the game. It was a little early for Madeline’s normal schedule, but with a day game it felt like now or never. Fortunately she fell asleep quickly and got in a little over an hour.

Then it was back to the ballpark.

It was a warm Midwestern afternoon, but some cloud cover helped keep things comfortable. My grandpa handled the walk better than expected, even if he wasn’t exactly thrilled about it.

Our seats were on the third-base side. When we first sat down we were baking in the sun. Fortunately the season-ticket holders next to us informed us that our seats would be shaded within about thrity minutes. They were exactly right. By first pitch we were perfectly comfortable.

It is always difficult to sweep a team, especially a good team, so we weren’t particularly optimistic heading into the game. Things got off to an ominous start when Angel Martínez hit Carlos Rodón’s second pitch of the afternoon over the fence for a home run.

Fortunately the Yankees answered immediately.

A pair of singles and a Jazz Chisholm triple quickly put New York ahead. Jazz later scored on an error and suddenly the Yankees led 3-1.

Rodón’s biggest issue this season has been walks, and in the fourth inning he walked the first two hitters. Both eventually scored. Still, Rodón settled in and gave the Yankees six solid innings while allowing only three runs.

A couple innings later Trent Grisham used ABS to overturn a called third strike. On the very next pitch he ripped a triple. That sequence completely changed the game. Caballero brought him home with a sacrifice fly. Then Jazz singled and stole second. Volpe followed with a hit, and Chisholm never stopped running. He scored all the way from first base. It is a good thing he has wheels because he is sorely lacking in good judgment, which makes him so fun (and sometimes frustrating) to watch. 

The floodgates opened.

The Yankees scored three runs in the sixth inning and added two more in the seventh. Suddenly it was 8-3 and the game felt firmly under control. 

Cleveland added one run in the ninth, but the Yankees completed the sweep with an 8-4 victory.

There were also some fun moments from our section.

My grandpa made friends with the guy sitting next to him, a Cleveland fan named Bob. The two chatted away for several innings until Bob and his friend were asked to move. As it turns out, Bob’s strategy was to buy a cheap standing-room-only package and then locate empty seats throughout the stadium. It worked until it didn’t.

During the middle innings Madeline started getting restless, so I took her on a popcorn run. That occupied her for quite a while.

Meanwhile, my grandma braved an incredibly long ice cream line. She missed a good chunk of a Yankees rally while waiting, but returned triumphantly with chocolate ice cream that she shared with Madeline.

It was one of my favorite moments of the trip.

There we were, sitting at a Yankees game, watching my grandma share ice cream with my daughter. Every time Madeline finished a bite she would politely say “please” to ask for another bite. It was adorable.

In the bottom of the eighth inning, David Fry hit a foul ball into our section. The ball ricocheted off a couple of people and landed directly on Alison’s shoulder.

Of course we gave the ball to Madeline.

She was thrilled.

Later a Cleveland fan sitting behind us told us he had been thinking that if he caught a foul ball, he was going to give it to “that cute little girl” anyway. It seemed like the baseball gods had already made that decision for him.

These were two fabulous baseball games. The Yankees won both, we saw some great moments, and we checked another ballpark off the list. Most importantly, we got to experience it all together.

After the game we made our way back toward the hotel. My grandpa was pretty tired from the walk and decided to stay in and eat leftovers. The rest of us headed out for dinner.

We went to a place called Fat Katz. The food was excellent, but my favorite part was watching my grandma dote on Madeline. She absolutely adores her. Madeline loved the cat-themed décor throughout the restaurant and was particularly fascinated by a dog statue near the bathrooms. She also devoured her mac and cheese, so dinner was a success on every front.

Afterward we stopped at Mitchell’s Homemade Ice Cream on our walk back. It was very good and Madeline was thrilled to have another little treat.

We dropped my grandma off at the hotel and then Alison, Mads, and I headed out for one last walk. We crossed the Hope Memorial Bridge as the sun began setting over Cleveland. Eventually Madeline fell asleep in her stroller and we slowed our pace a little. From the bridge we had incredible views of the skyline, Progressive Field, and the Cuyahoga River winding through downtown.

As we walked, I found myself thinking about how much fun the last couple of days had been. The baseball was great. The Yankees won both games, we saw a rookie hit his first career home run, Madeline got a foul ball, and we checked another stadium off the list. But more than anything, I was glad we had made the trip.

Traveling with grandparents and a toddler means the pace is a little different than it used to be. There are more breaks, more adjustments, and a little more planning involved. At the same time, those different generations together are what make trips like this memorable. It can be hard, but it is also very worthwhile. 

Eventually we made our way back to the hotel and called it a night. Cleveland had been a wonderful start to the trip, but tomorrow we would point the car toward Pittsburgh and begin the next chapter of our baseball adventure.