We recently spent six days traveling through St. Michaels, Annapolis, Chincoteague, and Ocean City. Part of the trip centered around a 3-day networking event in St. Michaels called Kinetic, but the rest unfolded as a mix of exploration, slow mornings, long drives, and unexpected moments that ended up shaping the entire experience more than we anticipated.

It wasn’t a perfectly planned itinerary. It was one of those trips where the best parts revealed themselves along the way.

St. Michaels: Kinetic, Conversations, and Slowing Down

The reason for our time in St. Michaels was Kinetic, a 3-day networking event for creatives and business owners. Going into it, we weren’t entirely sure what to expect. Over the years, we’ve both become a bit more intentional about the spaces we choose to learn from and the people we allow to influence our work.

What surprised us most was the culture of the event itself.

Instead of surface-level networking, we found ourselves in conversations that felt grounded and honest. People weren’t just exchanging business cards or talking about what they do—they were sharing how they think, what they’ve learned, and where they’re trying to grow. It set a different tone than what we’ve experienced at many industry events.

One of the biggest takeaways for us came from those speaker sessions and conversations: the importance of returning to your own instincts in business. There is no shortage of advice in this industry, but not all of it is meant for you. This trip reinforced something we’ve been learning over time—clarity comes from being more ourselves, not less.

Staying in the Heart of Annapolis

Before and after St. Michaels, we spent time in Annapolis, which quickly became one of our favorite stops on the trip.

The city immediately reminded us of Boston in the best way—historic, walkable, and full of character. We spent a full day just wandering, stopping wherever something caught our attention rather than following a set plan.

One of the highlights was staying in a local inn, 134 Prince, right in the heart of the city. The design felt warm and intentional, with a homey atmosphere that made it easy to settle in. Being able to walk everywhere from our stay made the experience even better. There’s something about not needing a car that changes how you experience a place—you notice more, you slow down more, and you end up stumbling into things you wouldn’t have planned.

We also had Matlock try soft shell crab for the first time, which has officially entered the list of “unexpected travel food wins.”

Ocean City, Chincoteague, and Finding Wild Horses

At one point, we weren’t even sure if we would make it out to see the wild horses. We had heard that sightings weren’t guaranteed and that timing mattered. Still, we decided to go anyway—and it ended up being one of the most memorable parts of the trip.

We drove to Ocean City expecting it might feel a little overrated or overly touristy, but it ended up being one of our favorite decisions of the entire trip. Not only did we get to experience a different coastal atmosphere, but it also put us much closer to Chincoteague and the areas where the wild horses roam.

We woke up early and made our way out to see them, not knowing if we would actually find anything. We got lucky. We saw wild horses on the beach two days in a row.

There’s something surreal about watching them in that environment—completely unbothered, moving through the landscape like they’ve always belonged there. It felt quiet in a way that’s hard to describe.

We took a lot of photos, but more than anything, it was the experience itself that stayed with us.

Matlock grew up on a horse ranch in Los Angeles, so it was especially meaningful to share that moment with his parents afterward. It was one of those experiences that felt personal in a way we didn’t expect.

The Unexpected Stops That Made the Trip

Some of the most memorable parts of the trip weren’t planned at all.

On the drive toward Annapolis, Matlock noticed an ice cream shop next to a field of cows and immediately wondered if the milk came from them. That curiosity turned into a spontaneous U-turn, and we ended up stopping to find out.

It turns out the ice cream was indeed made with milk from the cows right next door. Kelly grabbed a scoop and took a photo eating it with the cows in the background. It was one of those small, funny, very “us” moments that tends to happen when we travel together.

The ice cream itself wasn’t necessarily a favorite, but the experience definitely was.

Coffee Shops and Small Favorites Along the Way

A few places stood out throughout the trip that we’d absolutely go back to:

• Rise Up Coffee became an unexpected favorite. As self-proclaimed coffee snobs, we were pleasantly surprised by how much we enjoyed it. The food was also consistently good, and having a smaller location in Annapolis made it easy to stop in while exploring.
• Eat Sprout in St. Michaels was another highlight, especially for its fresh, healthy options that worked well during a busier travel schedule.

These kinds of spots always end up shaping how we remember a place just as much as the landmarks do.

What This Trip Taught Us

Looking back, this trip wasn’t just about visiting new places. It was a reminder of how we want to move through both travel and business.

We left Kinetic with a clearer sense of wanting to stay rooted in our own creative direction. There is a lot of noise in this industry, and it can be easy to get pulled in different directions. This trip reinforced the importance of filtering advice carefully and trusting our instincts more than ever.

It also reminded us how much we value traveling together. Whether it’s exploring a new city, finding a coffee shop we didn’t plan for, or driving across the state just to see what we discover, those shared experiences matter deeply to us.

And maybe most of all, it reminded us to slow down. To notice things. To stay open to the unexpected.

Maryland surprised us in every way. From the misty mornings and open landscapes to the small towns and coastal energy, it ended up feeling both unfamiliar and strangely familiar at the same time—like somewhere we already knew we would come back to.