The sixth county on travel experts Diane and Jeff’s twenty-three county and Baltimore City exploration of Maryland was Caroline County. Their approach continues to be outside adventuring, seeking out trails, rails and different parts of history, preservation, and adaptive reuse that were not explored deeply on their first go around the state.

FROM DIANE AND JEFF’S TRAVELOGUE:

Caroline County was created in 1774 from parts of Dorchester and Queen Anne’s counties. The county derives its name from Lady Caroline Eden, wife of Maryland’s last colonial governor, Robert Eden. Of course, Native Americans were living in Caroline County well before European settlers. Most of the land was claimed by Algonquin tribes under Chief Powhatan with the “subtribes” of the Choptank, the Delaware, the Matapeake, and the Nanticoke. Not much of the history is preserved, but we can only image those that lived on the land as we explore it today.

We headed first to Ridgley, to see their rails to trail project. The original railroad went from Ridgely to Oxford and stopped carrying freight and passengers in 1949. There is a beautifully restored 1892 train station, with much of the rail line still intact alongside the trail. Looking closely at one of the rail sections we could clearly see the imprint “Carnegie 1898.” Inside the Ridgely Pharmacy, was a small lunch counter, where we stopped for coffee and homemade pastries. 

Nearby Ridgely was the Adkins Arboretum, a 440-acre garden and preserve. Although it was November, it was an unseasonable warm day and lucky for us, still some fall colors to enjoy. The arboretum is on the Harriet Tubman Underground Railroad Byway that is “dedicated to promoting the appreciation and conservation of the region’s native plants. Walking along streams, over wetlands, and through woodlands allows visitors to experience the kinds of landscapes that freedom seekers on the Underground Railroad passed through on their way north.” Every tree name was marked and some of the educational signs made you stop and reflect like #31 – North Meadow – “All landscapes have a history. This area is a farm meadow grazed by dairy cows in the 1930s and 1940s. Children picked blackberries, rode ponies and searched for Native American artifacts.” It was just a beautiful walk in the woods.

Next stop was Denton, the county seat, established in 1781. It was a major trade center for the wider agricultural area and the Denton Wharf on the Choptank River was a busy loading point. We had and outdoor lunch at Market Street Public House then took our own tour of the downtown areas, from the county courthouse to the arts district and the wharf. As it was close to veteran’s day, there were banners on the streetlights honoring individual service members – “Caroline Heros” – throughout all the wars. We finished at Nich’s Coffee House for some iced coffee and treats to go.

Our final stop was Federalsburg to check out the Federal Brewing Company. Although it was not open the day we were there, it was fun to peek inside the 100-year-old bank building turned kombucha brewery. We took a walk over the Marshyhope Creek Bridge and checked out the public access canoe and kayak launch. Leaving Federalsburg, we stopped to admire the murals on the side of the town hall. It is part of the Caroline County Arts Trail and depicts scenes from eastern shore life. 

It was fun to explore Caroline County and discover some things we had not seen on our first visits. 

FOLLOW ALONG FOR MORE MARYLAND ROAD TRIP ADVENTURES

READ THE ANNE ARUNDEL COUNTY ROAD TRIP BLOG HERE

READ THE FREDERICK COUNTY ROAD TRIP BLOG HERE

READ THE CECIL COUNTY ROAD TRIP BLOG HERE

READ THE ALLEGANY COUNTY ROAD TRIP BLOG HERE

READ THE St. Mary’s COUNTY ROAD TRIP BLOG HERE

READ THE Caroline COUNTY ROAD TRIP BLOG HERE