The Baltimore and Annapolis Trail plus the BWI Trail are two distinct trails that connect at the northwestern trailhead of the Baltimore and Annapolis Trail via the John Overstreet Connector. So, back and forth to Annapolis is about 28 miles, then the loop around the Baltimore Washington International (BWI) Thurgood Marshal airport is another 10.5 miles.
We headed southeast on the Baltimore and Annapolis Trail, first alongside a runway (the parking lot is actually called the Thomas A. Dixon Observation Park) and then into the woods. For the next mile or so, we zigzagged through the forest until we came to a road sign that required us to stop and read it carefully. After crossing a highway bridge, we rode for the next 13 miles through a variety of settings.
There were many picturesque parts of the gently rolling trail: split-rail wooden fences along mowed grass aprons and large “mounds” of vine-covered trees. In many areas, the trail ran along the edges of well-kept neighborhoods where there were frequent, but not busy, intersections. Almost imperceptibly, the trail declined towards Annapolis – a fact we were only made aware of as we climbed back towards BWI. At about the 10-mile mark, we saw many bikers and runners stopped at a popular trailside coffee shop in Severna Park. This is the most convenient place to fill up on water or snacks. Next to it was an enormous pile of discarded bikes behind Pedal Pushers bike store.
After a few more miles of the quiet, mostly shaded trail, we reached the Annapolis trailhead then turned around. Thirteen or so miles later, we arrived back at the Observation Park and forced ourselves to do the BWI loop. Surprisingly, the BWI trail was NOT a tour of parking lots, airport hangars and shade-less runways. It was actually pretty in many spots and had an interesting array of vistas ranging from forests, to horse pastures, to overlooks of the airport, to neighborhoods, to highways. This is a very popular loop and one local biker told us that there were too many pedestrians to ride on the weekends.
Ireland’s most famous brewery has its only US brewery near BWI and it is both massive and a ton of fun.

Where the trail currently begins (in Milton, Delaware) is unmarked and there is no parking. We parked on the side of a little-used road (Cool Spring Road) and jumped on the trail at the intersection of the busier route US 9 East. (A good address to look up is the Brimming Horn Meadery which is right on the trail and very close to the western trailhead.) We took off on the smooth asphalt trail through an airy forest of very tall pine trees, whose canopies hovered about 30 feet above us. Riding along the flat-as-a-pancake trail, we passed by both new and more established neighborhoods where flags and flowers festooned the trail’s edge to welcome bikers and pedestrians. We’d read that there were 12 intersections along the trail, but very few had any traffic. It was a fast and easy six miles to the outskirts of Lewes, a quaint little beach town, and it is here that we transitioned onto the Lewes-Rehoboth trails, which make up essentially one big 17-mile loop.
We decided to head counterclockwise on the loop, riding south, then east, through cornfields, neighborhoods, open marshes, and wooded patches outside Rehoboth. The town itself is where you can find any number of stores or restaurants to buy food or water. After a fairly short jaunt through the neighborhood streets of Rehoboth, we rode on the wide shoulder of Ocean Avenue heading north along the coast. Soon we were entering Cape Henlopen State Park and riding on one of the most unique and picturesque trails we’ve ever encountered. It’s almost entirely marsh land, inland bodies of water, and sand dunes. Snowy egrets, gray herons and a wide variety of marine life populate the marshes. At various points along the trail, there are observation decks and places to view the ocean and the remains of abandoned World War II-era watch towers, artillery, and barracks. It was a little tricky winding our way out of the park but eventually, we ended up on a road that paralleled the beach and led back into Lewes. There’s a cute little brewery right on the trail, then another big name brewery – that is a favorite of ours – back in Milton.