Century Rides in Maryland
The comprehensive 2026 directory of 100-mile centuries, metric centuries (62 miles), and endurance cycling tours across Maryland.
Cycling in Maryland: Terrain & Route Overview
Known as 'America in Miniature,' Maryland packs an astonishing range of cycling environments into its borders. On the Eastern Shore, flat, paved farm roads skirt the marshy estuaries of the Chesapeake Bay, offering calm, wind-favored centuries like the famous Seagull Century in Salisbury—one of the largest and most beloved recreational 100-milers in the nation. To the west, the Piedmont region features manicured horse farms and rolling terrain, while Western Maryland challenges serious climbers with steep Appalachian ascents through Garrett and Allegany counties. With long spring and autumn seasons, excellent road infrastructure, and century aid stations serving fresh Chesapeake seafood and local treats, Maryland is a staple on the East Coast endurance cycling calendar.
Terrain Characteristics: Chesapeake Bay coastal plains, rolling Piedmont horse country, and Western Appalachian ridges.
Riding Season & Weather: April through June & September through November.
📍 Maryland Century Rides Map
12 Plotted EventsC&O Canal Towpath Century Challenge
AnytimeContinuous non-motorized towpath following the historic Potomac River corridor across Maryland.
Civil War Century
SeptemberA ride for everyone – Earn bragging rights on the long and mountainous routes, look at the mountains on the mid-length routes, or enjoy a short scenic tour. All routes are well marked, we provide access to Ride with GPS course downloads, and maps are posted at the rest stops.
Garrett County Gran Fondo (Diabolical Double)
JuneOne of the hardest centuries on the East Coast with severe mountain climbs around Deep Creek Lake.
Icicle Metric
AprilChoose from 3 routes of varying distances of approximately 13, 24 and 31 miles or combine them to get up to 68 miles covering moderately hilly terrain in the areas west and north of Newark, Delaware.
Indian Head 100
SeptemberRide on the Indian Head Rail Trail
Lifeline 100
OctoberScenic routes with water views and historic sites, inclusive event offering routes for cyclists of all ages and abilities.
Ride Ocean City
MarchA weekend of bicycle riding events, with Saturday's inaugural OC Criterium Race, followed by a casual bike tour on Sunday.
Sea Gull Century
OctoberThe Sea Gull Century is a classic 100-mile ride from Ocean City, Maryland, to Berlin, Maryland, with a metric century option.
Sugarloaf Century
JulyA century on the nose to the mountain closest to D.C. It’s quite a small mountain, but you’ll definitely be able to tell when you’re climbing it. Plenty of flattish parts, with rollers mixed in, especially the further out one rides from the District.
The Civil War Century
SeptemberA ride for everyone – Earn bragging rights on the long and mountainous routes, look at the mountains on the mid-length routes, or enjoy a short scenic tour.
Tour de Frederick
AugustScenic routes through rolling Frederick County countryside, crossing multiple historic covered bridges.
Tug Valley / Frederick Fall Classic
OctoberLate-season ride tackling the scenic ridges, valleys, and autumn foliage of western Frederick County.