My Summer Exploring Maryland’s Upper Shore

I’ve lived on the Eastern Shore since 2003, living in Ocean City, Berlin, Easton, and St. Michaels. Embarrassingly, it took me nearly 20 years to visit Maryland’s Upper Shore, and after several trips to Kent and Cecil counties last year, I realized just how much I had been missing out.

Trip 1

It all started when I signed up for a women’s kayaking course over a weekend in June 2023. During the drive there, I fell in love with the rolling hills you just don’t see anywhere else on the shore. The farmland and empty roads made me feel like I had stepped back in time, and I began wondering what this place was like a hundred years ago. I guess I was deep in thought, and I missed the turn to the Airbnb in Kennedyville and ended up driving through the tiny village of Still Pond. It was there I noticed a historic marker indicating that Maryland’s first women voters cast their ballots in Still Pond—talk about some awesome history! 

The kayaking course, led by world-class instructors, was phenomenal. I learned new skills, practiced rescues, built confidence, and made some new friends.

On Saturday evening, we enjoyed a fabulous meal at Molly’s Place, a fascinating establishment in the middle of nowhere. It was a full-service restaurant, gas station, and a high-end outdoor equipment store! You could fill up, have a beer, and purchase quality camping gear all in one stop.

Trip 2

A few weeks later, I was back on the Upper Shore, this time with my Aunt Margaret Ann. I wanted to explore more of the area, and it had been a while since the two of us hung out, so we made an overnight trip out of it. We booked an Airbnb in a historic home in downtown Chestertown, with plans to walk to a restaurant for dinner after paddling at Still Pond Station Park, a spot on my paddling bucket list. But as soon as we checked in, there was a deluge of rain and storms. We decided to relax and read at the Airbnb until it cleared up.

We did get to paddle later on, but we missed the chance to go out to dinner. I had hopes of trying out a place called The Retriever Bar which came highly recommended by our host, but instead, we enjoyed our sunset paddle and grabbed some take-out instead.

The next morning I got up early to paddle from Eastern Neck National Wildlife Refuge to Rock Hall. My aunt slept in and met me at Ferry Beach, where I ended my paddling trip.

We relaxed on the beach and enjoyed the stunning Chesapeake vista, and then headed into town for lunch. We ate at Java Rock Coffee House & Cafe, where we enjoyed delicious paninis and iced coffee while overhearing conversations of transient boaters who were staying at a nearby marina as they sailed the bay. 

After lunch, my aunt drove me back to my car, which was still parked at the refuge, and we spent some time exploring the trails and overlooks there.

The marsh boardwalks and observation platforms made for some incredible photo opportunities. Although the visitor center was closed that day, I was in awe of simply looking at the exterior, as it is a historic 1930s hunting lodge.

At the end of July, I returned to Maryland’s Upper Shore again. This time it was a day trip with my friend Kristyn. I had been hearing about the blooming lotus flowers for years, and it was finally time to see them in person. The only place on the Eastern Shore to see the American lotus is near the Sassafras River.

After dropping our kids off at camp and loading our kayaks, Kristyn and I enjoyed a leisurely drive up to Kent County. We launched at a boat ramp in Fredericktown and paddled about two miles to Woodland Creek. 

The flowers were absolutely stunning—big, giant white blooms surrounded by enormous lily pads. We were careful not to disturb the plants too much and stuck to paddling just the outside of the lotus patch. 

Trip 3

In early October, my husband and I celebrated our 10-year wedding anniversary. His parents came to watch our son, and we took an entire week off to celebrate. We explored Delmarva from top to bottom, which included adventures on the Upper Shore. We went for a short paddle out of Stemmer’s Run, where we saw countless bald eagles, a few lingering osprey, and a glimpse of the Turkey Point lighthouse across the Elk River. 

The next day we headed to Chesapeake City and took advantage of the self-serve bike rentals provided by Fin Outdoor Recreation. We biked the Ben Cardin Trail, which took us along the C&D Canal and into Delaware.

The views of the canal were lovely, and biking under familiar bridges provided a really cool, new perspective. Now, for people who aren’t regular cyclists, I don’t recommend doing the full 30-mile trip to and from the Delaware River, as my legs were like jello the next day!

Before we continued our trip down to Virginia, we spent one night in Chestertown at an Airbnb just outside of town. After settling in, we headed into town and enjoyed a stroll on the rail trail before heading to dinner. I finally got to try The Retriever Bar, and it was definitely worth the wait! It was the best meal we have had in years.

We ordered cocktails we had never heard of, oysters from a local oyster farm I visited last year, and fresh, locally sourced entrees. I had the mushroom risotto and dreamt about it for days afterward. My husband even ordered dessert, which is something he never does!

Needless to say, I will be back to explore more of Maryland’s Upper Shore in 2024.

Feature Photo: Eastern Neck National Wildlife Refuge in Maryland. Feature Photo Credit: Laura Scharle