For those of you who followed the Maryland road trip experts Diane and Jeff Caslow on their first adventure to explore every county in Maryland over a two-year period, they’re back again, and this time, with a twist! In this first blog post of the new series, Jeff and Diane navigate travel, shopping, and dining in the world of social distancing in Anne Arundel County.


Given the way our lives have changed with COVID-19, my husband Jeff and I thought we would revisit the counties from a lens of being outside, while still weaving in history, preservation, adaptive reuse and ways to eat and shop local. So off we went to Anne Arundel County as our first county to explore. As this was our first trek being mindful of COVID-19 precautions, we had ordered Maryland flag masks from Route One Apparel, mine with my Preservation Maryland pin added.

The Baltimore & Annapolis Trail

We started our day with a walk on the B&A Trail, picking it up at the Park Ranger Station and Railroad Museum in Severna Park, which was built in 1889 as a general store. This beautifully flat and somewhat shady trail was perfect for a walk on a hot June day.  The trail is named for the old “Annapolis and Baltimore Short Line Railroad.” The first run was in 1887 and the last run for passengers was in the 1950’s. It converted to freight only and ceased operating completely in 1992. It’s conversion to a trail began in 1985 and opened for use in 1990. I like to think of these old rail beds as nice examples of adaptive reuse for anyone to enjoy. Halfway through our walk we found not only the old Severna Park station, but a popular local coffee shop, The Big Bean, with a carryout window. There were bikers and walkers socially distancing while enjoying a cool drink on a hot morning as a nice stop along the trail. 


Leaving the trail, we next stopped in Annapolis. We decided to just walk the streets a bit in downtowncame across an online order-ahead plant market, window shopped, and rounded out with a quick purchase in the Old Fox Bookstore for intended use later in our day. As outdoor dining had just started, we enjoyed an outside table at the Middleton Tavern, established in 1750. I also thought that a requirement for any of our summer adventures had to include ice cream. Storm Brother’s in downtown Annapolis did not disappoint. Heading out of Annapolis, we saw one of the sites mentioned in the “Guide to African American Heritage and Culture in the Four Rivers Heritage Area.” The Asbury United Methodist Church, one of the oldest congregations in Annapolis, sits on land purchased in 1803 from Smith Price, a free black man. The Fourth Ward grew up around the church, but many businesses and homes were lost to growing government footprint and urban renewal in the 1960s and 1970s, not uncommon in cities across the country at the time. 

Historic London Town and Gardens

I picked out the next stop, Historic London Town and Gardens, because I wanted to include a garden in our day’s adventure.  It was once a colonial seaport established in 1683. The gardens took us along flowering walking paths, through wooded areas and down by the South River. I had thought we could pull out the books we purchased and begin reading in the gazebo in the garden, a nice way to spend more time in the garden. However, it was just too hot, so Jeff took a quick picture of me in the gazebo of what could have been. In addition to the garden, only a few of the building were open for self-guided tours, including the reconstructed tenement house and the carpenter’s shop. The tenement house had an exhibit entitled “Our history cannot be told without slavery” and is part of a larger UNESCO Slave Route Project. We came for the gardens and got an important history lesson woven in too.

Highland Beach

We thought we would follow one more stop from the guide as we headed back toward Annapolis.  I was interested in seeing what the private African American beach resort, Highland Beach, looks like now over 100 after its founding. 

More about Highland Beach’s History:

Highland Beach was founded in 1893 by Charles DouglassFrederick Douglass’ son, and his wife after they had been turned away from a restaurant at the nearby Bay Ridge resort because of their race. Charles Douglass was a retired officer formerly with the 54th Massachusetts Colored Infantry. Douglass had been denied access to a restaurant on Chesapeake Bay because he was African American, so he decided to buy beachfront property directly south of Bay Ridge and sell lots to family and friends.  The couple bought a 40-acre tract on the Chesapeake Bay and they turned it into a summer enclave. Their own home, the Douglass Summer House, was listed on the National Register of Historic Places in 1992.  It became a gathering place for upper-class African-Americans.  When Highland Beach was incorporated in 1922 it became the first African-American municipality in Maryland. It is now a town of year-round residents.

The guard at the gatehouse let us in to take a driving tour of the community and beautiful beaches.   


Our last stop was Eastport, settled in 1665 and remained largely farmland until the 1800’s. The first bridge was built in 1868 to connect to Annapolis across Spa Creek. In 1950, the independent town of Eastport officially became part of the City of Annapolis.  In keeping with our outdoor adventure, we trek along the waterfront with Jeff pointing out some of the buildings that used to build major wooden boats over 100 years ago. Forward, a relatively new brewery provided walk up service to grab some of their signature beers to enjoy later. Last drive by for the day that few would notice in its original form is Davis’ Sweet Shop, opened in the 1930’s to serve the African-American community. It now Davis’ Pub, and a local hangout for the community serving up different kinds of “sweets” today.  

This was a fun way to begin to re-explore Maryland, finding things that could keep us outside for pretty much the entire day.  We always are discovering something new in Maryland and hope you enjoy the start to our new adventure.