Classic Beach & Boardwalk Day in Ocean City, Maryland

The kids are back to school, which typically means summer’s over . . . but I’m not done with it yet! This year we took an unforgettable trip to three destinations on the east coast. Here’s everything we did in Ocean City, Maryland.

Earlier this year I was planning our summer family trip when an article came out from Conde Nast: “The 17 Best Beach Towns on the East Coast.” I love a good travel article like this. I scan to see where I’ve been and what I should add to my ever-growing list. Was I thrilled to see our vacation destination of Chincoteague, Virginia make the cut! The seventeen locations started at the top of the country and worked its way down. Just before Chincoteague was Ocean City, Maryland. I don’t know why that stuck out to me, but I looked it up and it was just over an hour north of the eastern shore of Virginia, in fact separated only by the long, thin island of Assateague.

My mind started doing calculations like the meme of the lady’s face with all the math equations floating around her. Chincoteague was supposed to be a small, laidback town which has a wild, rugged beach nearby. But Ocean City is more of the classic American east coast beach, with a popular shoreline and entertainment-packed boardwalk. The kids would love it, and have never been to a place like that yet. If we left a day early, drove straight there . . . I started researching hotels.

The route is over fourteen hours from Chicago. We did it in one day, and let me state for the record that I am incredibly appreciative and in awe of my husband who can drive overwhelming stretches at a time! We left before dawn, stopping as minimally as possible except for lunch, which I had planned for us to have at the Big Mac Museum outside of Pittsburgh, Pennsylvania. Whenever we go somewhere, I look to see what foods are famous, what originated there, where the historic dining establishments are, etc. Once I stumbled on the fact that there was a McDonald’s just off the highway route celebrating the invention of the Big Mac, I knew that was where we had to go! It totally fit with my theme of visiting the fast food chain in other countries, and you didn’t need to convince the kids.

The “museum” is really just a McDonald’s with some nostalgic displays of memorabilia and a giant Big Mac statue in the window of the PlayPlace. We ate, our youngest played (immediately followed by hand washing), we snapped some photos, and were back on the road.

On the way, we admired the hilly Pennsylvania turnpike terrain and noted the turnoff for the Flight 93 memorial, the Appalachian Trail bridge which we drove under, and the nearby site of the Battle of Antietam. We pulled off to a rest stop which had commemorative plaques about the locations as well. We then ogled the crazy long bridge over Chesapeake Bay, as well as several other bridges we had to cross. In Dorchester County, Maryland, we saw so much Harriet Tubman content that I looked it up and realized with amazement that was where she was born a slave and later escaped. One of the reasons I love the east coast is that it is so abundant with history to learn from and beauty to behold, and I regretfully accepted that we didn’t have time to explore it all.

As the sun dipped below the horizon and the blue hour dimmed into darkness, we saw the neon lights of Ocean City dazzling the waters ahead. The kids got excited. We immediately sensed from the retro, touristy attractions that the town is like Niagara Falls, but by the sea. Maybe not for everyone, but fun for what it is. We made it to the hotel, ate some food we had packed, and got the kids in bed. Anthony and I stayed up and had a drink in the lobby before turning in. The next day our vacation would truly begin.

I woke up at sunrise (yes, I set my alarm) to catch the sky do its morning show over the strip of ocean we could see from our room. Then I went back to bed until the rest of the family stirred. We ate breakfast downstairs, changed into our suits and coverups, packed up the rest of our stuff, stored it in the car, and checked out. It was super convenient that the hotel had a free parking lot, and we could leave our things while we went to the beach across the street.

The weather was hot and sunny, just perfect for swimming, so the shoreline was crowded, but we threw our stuff down and jumped into the crashing, salty waves. The Atlantic was so warm, like bathwater! But it was strong and knocked our littlest over. It took her a bit to get the hang of it and then she purposefully stood where the cresting water would batter her. For hours, all four of us were happy little lobsters swimming around in the pot. We’d swim, then chill on the sand, then swim, rinse and repeat.

Finally hunger got the best of us, so we packed it up, brushed the sand off, and walked to a nearby casual Italian place called Ripieno’s. The lady behind the counter was really nice, and as soon as I uttered the word “pop,” while ordering beverages, she clocked us as Midwesterners. Turns out, she was born and raised in Madison, Wisconsin, but had long called Ocean City her home. We devoured their antipasto salad, mozzarella sticks, and allegedly “authentic” cheesesteaks (we wouldn’t know, but they were very good).

After lunch we drove a short way south to park near the boardwalk. It’s just like in the movies: a wooden walkway extended down a length of the beach, lined with restaurants, arcades, a Ferris wheel, and souvenir shops. Of course the kids wanted to shop. I had to refrain from buying myself a stuffed animal seagull with a French fry in its mouth. Around us, funny seagulls squawked and hovered, looking for their next bite.

A requisite was to get scoops of the famous, longstanding Dumser’s Dairyland Ice Cream. Every place we travel to has its own renowned frozen dairy dessert. It was really delicious, thick and tasty, giant scoops that dripped down your arm in the heat. I can never eat an ice cream cone fast enough to not get messy!

I also had to get the celebrated Thrasher’s Fries. I watched the staff cut fresh potatoes in a contraption, plunge the spuds into hot oil, salt, and then scoop into the carton, precariously loading quite possibly more fries on top than were contained within. The other customers and I laughed as we tried to balance our snack, carefully treading like tightrope walkers as we exited the stand. We were still full from ice cream so I was barely able to make a dent in the fry pile, but I am team salty over sweet, so I did my best!

We wanted to get to our next location, Chincoteague, while it was still light out, so after a brief stop at the SMILE, Ocean City, Maryland sign for photos, and a quick jaunt at a candy store (which would be the first of many times we would notice the prevalence of Dubai chocolate knockoffs for sale on counters everywhere), we navigated the town’s one-way streets, making one last stop at Anthony’s Liquors, an unassuming place with retro signs that’s a sort-of hidden gem with an amazing deli in the back. We ordered a humongous American-style hoagie to take with us, and my Anthony got himself a cap with the store’s logo on it, natch.

Our route took us out the way we came in, and as we waved goodbye to Ocean City, I said one more silent prayer of gratitude for a perfect family day at the beach. If you find yourself in the Delmarva (Delaware, Maryland, Virginia—I would come to learn) area, Ocean City is a place to capture that timeless feel of an American outing to the seashore.