Discover the best recreation events in Talbot County, Maryland—from scenic runs to cycling tours. Explore the C3 Tri-County Ice Cream Classic, St. Michaels Running Festival, Tour de Talbot, and the Historic Drawbridge Running Festival.
Run, Ride, and Explore Maryland’s Eastern Shore
From cycling past miles of shoreline to running through charming waterfront towns, Talbot County is the perfect place to get active outdoors. Each year, our community welcomes athletes and enthusiasts to a series of signature recreation events that celebrate fitness, fun, and the natural beauty of Maryland’s Chesapeake country. Whether you’re a seasoned runner, a weekend cyclist, or just looking for a fresh way to explore the region, these events offer something for everyone.
C3 Tri-County Ice Cream Classic
Location: Easton, MD
When: Spring
Type: Cycling event
Cyclists from across the Mid-Atlantic flock to this sweet summertime ride that travels through Talbot, Caroline, and Dorchester Counties. The C3 Tri-County Ice Cream Classic offers multiple route options, from family-friendly spins to challenging 100-mile rides—all ending with a celebratory scoop of ice cream. It’s the perfect blend of community spirit, scenic beauty, and old-fashioned fun.
St. Michaels Running Festival
Location: St. Michaels, MD
When: May
Type: Running event
Every spring, runners take to the streets and waterfront trails of St. Michaels for one of the most scenic running festivals in Maryland. With a flat, fast course that winds past historic homes, marinas, and harbor views, the festival features a 5K, 10K, and half marathon. The post-race party is legendary – filled with live music, local food, and small-town hospitality that keeps participants coming back year after year.
Tour de Talbot
Location: Easton, MD
When: Summer
Type: Cycling event
The Tour de Talbot is a can’t-miss ride for anyone who loves cycling the Eastern Shore. Organized by Talbot Thrive, this ride supports local bike and pedestrian initiatives while showcasing the county’s quiet backroads, farmland, and waterfront views. With multiple route lengths and well-stocked rest stops, it’s a welcoming event for cyclists of all ages and abilities.
Historic Drawbridge Running Festival
Starting Location(s): Tilghman Island, MD and St. Michaels, MD
When: Fall
Type: Running event
The Historic Drawbridge Running Festival offers one of Maryland’s flattest courses, making for a true Eastern Shore classic. Marathon runners cross the iconic Knapps Narrows Bridge, taking in river views and tree-lined streets along the way. With waterfront views at every turn and a community that turns out to cheer, this event blends fitness, heritage, and hospitality in true Talbot County style.
A County Made for Moving
With its flat terrain, scenic byways, and inviting waterways, Talbot County is a natural playground for athletes and outdoor enthusiasts. Whether you prefer to run, ride, or simply cheer from the sidelines, these events offer a front-row seat to the landscapes and communities that make Talbot County so special.
Plan your trip around one of these recreation events and discover why Talbot County is where fitness meets fun on the Chesapeake.
