7 Most Bike-Friendly Towns in the Chesapeake Bay
The Chesapeake Bay region, located between Virginia and Maryland, is a beautiful part of the Eastern Seaboard that’s known for its rich history, diverse ecosystems, and thriving coastal communities. This area of outstanding natural beauty stretches for over 200 miles and provides plenty of exciting opportunities for two-wheeled explorers to have fun. Best of all for cyclists, the Bay is surrounded by many charming small towns like St. Michaels, Cape Charles, and Easton that have fully embraced the biking culture and actively promote cycling as a means of exploring their unique offerings.
With plenty of trails, parks, and cycling events to boast about, the Chesapeake Bay area has indeed become an increasingly popular hub for cyclists. In addition to their stunning coastal views, fascinating historic sites, and lovely rural beauty, they are also home to accessible cycling routes, bike-friendly businesses, and an active bike-centric culture. Find out more and plan your next cycling getaway to seven of the most bike-friendly towns in Chesapeake Bay.
St. Michaels, Maryland
St. Michaels, a quaint town on Maryland’s Eastern Shore, offers an idyllic blend of historic charm and coastal scenery that appeals to tourists. Its proximity to the Chesapeake Bay Maritime Museum and the town’s scenic waterfront makes it a top destination for cyclists seeking a fun excursion that includes a mix of history, nature, and plenty of pedaling. For the ultimate bike adventure, hop aboard the Oxford Bellevue Ferry for a unique bike-and-ride experience that crosses the Tred Avon River, leading to quiet country roads that are perfect for a leisurely ride.
St. Michaels also offers several cycling-friendly events, such as the St. Michaels Century, drawing cyclists from across the region for a safe and fun-filled ride. Need a rental or repair? Cyclists will find plenty of support in town from local businesses like Shore Pedal & Paddle, which provides these and other services. For those looking to explore more, the nearby Chesapeake Views Scenic Byway offers a stunning 85-mile route along the water.
Easton, Maryland
Easton is another popular cycling destination in Maryland that has easy access to Chesapeake Bay. Popular for its well-preserved historic downtown area and its extensive network of trails, this charming town provides riders easy access to pleasant scenic rural landscapes and quiet, tree-lined streets. Easton Historic District is a popular starting point for cyclists, with the Tuckahoe Valley trail system just a short ride away. These trails provide a mix of flat and rolling terrain, perfect for riders of varying skill levels.
Local non-profit groups like Talbot Thrive host regular rides that explore the countryside and connect riders to nearby towns. The town is also home to businesses like Easton Cycle & Sport, offering rentals, sales, and repairs when needed.
Cape Charles, Virginia
Over on Virginia’s Eastern Shore, Cape Charles is a quaint bayside town perfect for cyclists exploring the Chesapeake Bay region. With its flat terrain, charming historic district, and scenic waterfront, Cape Charles offers a relaxing yet enriching biking experience that encourages riders to cruise through the town’s tree-lined streets, passing by Victorian-era homes and must-see landmarks like Cape Charles Harbor. The town’s beaches also provide a scenic backdrop for leisurely rides with excellent views of Chesapeake Bay, plus a chance for a cooling dip.
Cyclists can also explore the nearby Cape Charles Natural Area, a 50-acre coastal preserve that features trails winding through dune and marsh landscapes. The Eastern Shore Rail Trail, a 49-mile multi-use path connecting Cape Charles to other local communities, promises to be a major cycling route once open. The annual Between the Waters Bike Tour is a lot of fun and features 25, 40, 60, and 100-mile options along the Eastern Shore, with most routes passing through Cape Charles. Need a rental or fancy a guided tour? SouthEast Expeditions provides both, as well as fun kayak adventures.
Cambridge, Maryland
Cambridge’s location along the Choptank River, where it empties into the Bay, makes it an ideal spot for biking enthusiasts interested in exploring a mix of urban and natural environments in Maryland. The town's waterfront views and historic downtown are key highlights, with cyclists enjoying the combination of quiet streets and the scenic beauty of the area. Specifically, routes like Water Street and High Street offer a serene local for some pedaling fun.
Natural highlights include the Blackwater National Wildlife Refuge, a 28,000-acre sanctuary for birds that’s home to miles of flat, scenic bike trails through a mix of marshland and forests. Didn’t bring a bike of your own? That’s ok, as River Dog Outfitters is a key resource for cyclists, offering rentals and repairs for visitors and locals alike. Afterward, one can refuel with some drinks and snacks at RAR Brewing in town.
Chestertown, Maryland
Situated on the Chester River, Chestertown combines its historical significance with some excellent cycling opportunities, making it an ideal getaway destination for people into pedal power. A highlight of Chestertown’s cycling calendar is the much-anticipated Chestertown Bicycling Weekend. Held each May since 1984 and organized by the Baltimore Bicycling Club, this three-day cycling extravaganza includes overnight stays in Chestertown, along with live music and plenty of opportunities to mingle with like-minded riders. It also boasts various levels of rides, from 10 to 100 miles, so everyone can join in on the fun.
Back in town, the quaint colonial-era streets and its proximity to several scenic waterfront trails make it a favorite among cyclists. Visitors can start their day exploring the Chestertown Historic District before venturing out onto the surrounding country roads that wind through picturesque farmland. Or, bike along the quaint routes in Wilmer Park.
Oxford, Maryland
Oxford is one of Maryland’s oldest towns and is a perfect destination for those who want to explore the state’s rich history. Popular amongst casual riders for its quiet streets and pleasant waterfront, it’s a delight to explore on two wheels, with local businesses like Oxford Social Café eager to serve cyclists. There are plenty of options for memorable rides, including hopping aboard the Oxford-Bellevue Ferry to explore surrounding areas for a 33-mile ride along the Oxford Loop. This popular countryside route includes a ferry ride over the Tred Avon River.
Need an excuse to visit? The annual Tour de Talbot, a fun, scenic ride offering 31.5, 40, or 61.5-mile routes, also passes through Oxford, making it a significant stop for cycling events in the region.
Annapolis, Maryland
The last stop is Annapolis, the state capital of Maryland and a key Chesapeake Bay cycling destination. This extremely picturesque spot offers many great cycling opportunities, particularly for those interested in urban and scenic biking. The town’s Naval Academy and historic downtown provide a unique setting for rides. At the same time, the B&A Trail (aka, the Baltimore and Annapolis Trail) connects Annapolis to nearby communities, offering 13 miles of tree-lined paths.
The town is also home to several annual cycling events, with the Annapolis Bicycle Club offering a variety of group rides and bike-related events. Need cycle-related gear? Annapolis Velo have you covered and also offer bike rentals, repairs, and even guided tours of the area.
The Final Word
The Chesapeake Bay area of the USA's Mid-Atlantic region presents many biking opportunities suitable for casual and hard-core riders. Some of the best of these can be enjoyed by basing yourself at one of this scenic region’s picturesque and bike-friendly small towns, each providing a welcoming environment for cyclists. Supported by dedicated infrastructure, thriving local businesses, and numerous trails that span everything from peaceful country roads to more challenging paths through wildlife refuges and nature preserves, biking in the Chesapeake Bay allows for a unique East Coast experience. Whether you're a casual rider or a seasoned cyclist, these seven most bike-friendly towns in Chesapeake Bay are eager to see you.
