They say some of the best stops are the ones off the beaten path, and Leonardtown is a perfect example. Once a sleepy stop on the old Chesapeake steamboat route, this town has found new life with a revitalized downtown and a fabulous waterfront

The highlight for any boater is the town wharf—easily the nicest free dock on the Chesapeake. It’s a sailor’s dream: floating aluminum piers, complimentary electric and water, and clean restrooms. If it only had showers, it would be absolute perfection. The adjoining park, with its playground, shaded benches, and green space, makes it an ideal spot to tie up and enjoy land access for a couple of days.

I arrived on the first weekend of June, just in time for a special event with concerts and rides free trolley. On Saturday, I headed inland to a Planet Fitness. My healthcare provider gives me free access to hundreds of gyms nationwide, which is my secret to getting a hot shower when I’m out traveling on the bay. While I was there, I hit the grocery store to restock a few low-running items.

Later that day, downtown Leonardtown was buzzing with people who had gathered for the bands, most having brought their own folding chairs. I, of course, had not. I circled the crowd, searching for a curb or a ledge to sit on, when I spotted an empty chair next to a large security guard behind the stage. I asked if it was available, and to my luck, it was. The position behind the band helped buffer the volume, and I enjoyed a couple of decent rock bands before the music turned to country—my cue to leave.

For dinner, I took a break from eating on the boat and headed to the Slice House for pizza by the slice. It was a great choice.

When I walked back, the park and dock were full of people. A stunning 40-foot Block Island Hinckley had tied up, and I couldn't resist going over to swap a few sailing stories with the owner. It was a perfect end to the evening.

Sunday was simply a peaceful day of rest. Tomorrow will be a long trip back out to the mouth of the Potomac, but thanks to Leonardtown, I’m heading out well-rested.