Outdoor Fitness on the Shore

When moving to the shore, the first thing that comes to mind is the beautiful scenery, and spending time outside is something you’ll truly enjoy! Water sports are a natural focus for the area, but there are also plenty of opportunities for land based activities.

We have local team sports, running clubs, cycling groups, races and more! From parks to trails, or just lovely walks in our historic downtown, your options are only exceeded by your willingness to explore.

A great place to start in downtown Chestertown is the Wayne Gilchrest trail, a a project from the Rails to Trails Conservancy, an organization that converts abandoned railroad tracks into fitness trails across the country. This 1.2 mile paved trail provides a protected pathway in downtown Chestertown that is perfect for walking your dog, heading out on a run, or going for a nice bike ride!

Depending on how far you like to run or ride, this can be either just right, or a great start to a longer journey! If you’re looking for a longer adventure, I still recommend making this trail at least part of your route.