We’re feeling very fortunate that the weather on the Eastern Shore has not yet shifted to bitter cold, and we’re thinking about new places to explore.  On a recent trip to St. Michaels we found some amazing outdoor spaces to enjoy, and have plotted out a few more to return for in the summer!

One of St. Michaels most prominent outdoor spaces is their 1.3 mile nature trail.  The trail runs parallel to Talbot Street from Heathington Farm Road to Railroad Avenue.  We recommend parking at Bradley Park off of Railroad Avenue where you’ll find a small playground with slides, swings and the northern trailhead. The trail is very easy to walk or bike, and is paved throughout. While traveling the trail you’ll find a covered bridge and water views.  Since this trail is not a loop, we enjoy walking the full trail, turning back, and then taking Chew Avenue (just before you reach the covered bridge) to walk downtown the rest of the way to Railroad Avenue.  Whether you’re looking for a snack or to do some window shopping, this is a great option. While Railroad Avenue does not have a sidewalk to get back to Bradley Park, we’ve found that it’s an easy walk. Another great parking option for this trail is located across the street from the Bay Hundred Pool.

From Memorial Day to Labor Day, Bay Hundred Pool is a great community area to enjoy, requiring a small admission. For a quiet place to sit on the water, we love the Waterfront Park on Miles River.  Parking here is very limited, but it’s a great place to watch the boats sail by.

One of the best ways to enjoy St. Michaels outdoors is by water.  Shore Pedal and Paddle in St. Michaels rents kayaks, bikes and paddleboards.  Enjoy paddling San Domingo Creek, where the water is flat and calm!  If your arms aren’t up for the challenge, consider an educational sail on a skipjack, the Chesapeake Bay’s traditional oyster dredging vessel, or a luxury sailing tour aboard a historic yacht.  For those looking for a larger vessel with air conditioning and a snack bar, consider cruising on the Patriot.

Join us in experiencing as many outdoor adventures as possible before winter’s chill sets in too deep!