One of the Best Cycling Spots in the U.S.? It’s Maryland.

What comes to mind when you think of Maryland? If you’re like most people, you think of it as a quiet, unassuming state, known mostly for its cultural center of Baltimore. Or maybe—with its proximity to Washington, DC, and as the home of the U.S. Naval Academy in the capital of Annapolis—you imagine nondescript government buildings that carry out the administration of statesmen and women. 

But a cycling destination? 

Well, yes. It’s one of our favorite places to head out for a spin. 

Nicknamed “America in Miniature,” Maryland boasts all the ingredients of a cyclist’s haven. A stunning coast along the Atlantic and Chesapeake Bay, rolling hills dotted with oak and pine, and gentle mountains that reach into the Virginias in the west. If you haven’t ridden here yet, you’re missing out. 

For us, the gentlest and most scenic rides unfurl on the Delmarva Peninsula east of the Chesapeake Bay, which curls up from the Atlantic like a finger and splits the state in two. Sea breezes and the clean ocean air are your constant companions along easy routes that link wildlife refuges, vast agricultural lands, and historic towns and culture-rich villages founded on boatbuilding, fishing, and oyster farming. It’s a coastal idyll like no other. 

Coast into a Rich Maritime Past 

The seafaring past lives proud here under open skies. Boat building fueled the early economy and still plays a part today, perhaps best embodied in the Oxford-Bellevue ferry that crosses the Tred Avon River. It’s the nation’s oldest privately owned ferry still in operation—and it saves a lot of mileage and time for anyone wishing to get from Oxford to Bellevue!  

For more insight into the region’s rich past, browse the Chesapeake Bay Maritime Museum in St. Michaels. Across an 18-acre campus, 35 buildings tell stories from the bay’s geologic, economic, and social past. A working boatyard is here so you can see the artisans at work, as is the Hooper Strait Lighthouse, built in 1879 and once threatened by demolition, and the world’s largest collection of Bay boats and skipjacks—some 100 vessels. You’ll only see real skipjacks in Maryland. These unique boats were first built in the late 1800s specifically to dredge the shallow waters of the Chesapeake Bay for oysters. If you join VBT in Maryland, you’ll sail into history aboard a restored skipjack with its seasoned skipper. 

Uncover Layers of History 

History lives and breathes here, and it’s pure pleasure to explore. In fact, this storied area is home to no fewer than 62 properties and districts that are listed on the National Register of Historic Places (NRHP). The Easton Historic District exudes endless charms, thanks to its array of 18th, 19th, and 20th century buildings that line its grid-patterned streets. Browsing its galleries and shops, you won’t be surprised to learn that it’s consistently voted on to “best small towns in America” lists. Also on the NHRP, Oxford is one of the country’s oldest towns. Though it was founded in the 17th century, much of its growth occurred much later, so most of its buildings date to the late Victorian era.  

The NHRP town of St. Michaels along the Miles River is best explored on foot, though a leisurely spin will also help you absorb its distinctive character. Its homes and downtown were mostly built in a variety of styles from the 19th century. Today, it’s a rich patchwork of Federal, Gothic, Revival and Italianate architecture. Finally, many buildings in Chestertown are also listed on the NHRP. This pretty tree-lined town was established in 1705 and was one of the English colony of Maryland’s six Royal Ports of Entry. Shipbuilding earned it much of its wealth, still visible today in its brick mansions and townhouses.  

Savor Natural Beauty and Culinary Treasures  

From colonial history to natural history, the Eastern Neck Island National Wildlife Refuge is a magnet for some 250 bird species. Cast your gaze into the trees to spot many of them as you stroll its scenic boardwalk through marsh and woodland. Keep an eye out for bald eagles, osprey, herons, and kingfishers waiting to pluck a quick meal from the waters. 

The majestic birds aren’t alone in waiting to savor their next meal. The farmlands of the Atlantic Coastal Plain might have you dreaming of dinner, too. Rides along tranquil byways and shaded lanes skirt fields of wheat, corn, and soybeans and offer serene vistas of the peninsula’s many waterways. These lands—and the waters that surround them—contribute to some of the finest cuisine in the East. There are the oysters dredged by the skipjacks, of course. But this fertile coastal region offers so much more: sweet scallops, steamed crabs (not boiled), crab cakes, and any number of fresh meats and produce from local farms.   

And what better to pair with all this glorious locally sourced food than a glass or two or wine? Eastern Maryland has that covered, too. Many vineyards specifically grow grapes to pair with the delicious seafood and farm products here, their plump fruits nurtured by warm days and Atlantic moisture.  

Discover the cycling pleasures of Maryland for yourself with VBT!