Century, Metric-Century, and Family Bike Rides in 2023

Nothing says, “Get Training,” like signing up for a “Century” (100 miles) or “Metric Century” (62 miles) bike ride as an incentive to start peddling. New to cycling? Most of these annual cycling rides also have shorter routes.

The rides listed are all fundraisers and they have a fee. But that means they’ll be watching out for you with people available to repair bikes or pick you up in emergencies. Usually, they’ll have rest stops with energy snacks and water.

It’s cheaper the earlier you register. I’ve waited until the day of to register because I wanted to check the weather first, but be aware that some don’t allow that. Check the rules.

For fun cycling routes to train on, check out our “Cycling” page.


End Hunger in Calvert County Bike Ride

End Hunger Bike Ride

HUNTINGTOWN, MD – Ride the western shore of the Chesapeake Bay along the bay-front, marina, farmland and wineries. Routes ranging from 16 miles to a metric century.


Cost: $39 to $49

Bikes and Beer cycling ride

Bikes and Beers: Smoketown Brewing

FREDERICK, MD – A 15-, 30-, and 50-mile ride departing from Smoketown Brewing and traveling through the moderately hilly Frederick area.


Cost: $75

C3 Cycling Club ride on Oxford ferry

C3 Tri-County Classic

EASTON, MD – Ride through Maryland’s Eastern Shore, along the Chesapeake Bay, through beautiful farmland and woods on these mainly flat 23-, 38-, 64-, and 103-mile courses. The routes go through beautiful Oxford, MD, with a stop at the ever-popular Scottish Highland Creamery, opening early to dish out ice cream for the cyclists, and ending with a Chesapeake Cycling Club welcome-to-Easton party with beer and a band.


Cost: $55, no day of registration

Ocean to Bay Bike Tour

Ocean to Bay Bike Tour

BETHANY BEACH, DE – Delaware’s Atlantic Ocean shores to Delaware Bay. Cyclists of all levels tour past beautiful beaches, bays, and farmland with 30-, 50-, metric century, and century rides on flat terrain


Cost: $65 – $75, no day of registration


End of Six Pillars Century ride in Maryland

Six Pillars Century Blackwater Tour

CAMBRIDGE, MD – This ride through Blackwater Wildlife Refuge has three flat routes: 37-, 56-, or 100-miles.


Cost: $60

Baltimore Kinetic Sculpture Race

Baltimore Kinetic Sculpture Race

BALTIMORE – Kinetic Sculptures are amphibious, human powered works of art custom built for the race. The race covers 15 miles and cyclists follow along to watch the challenges along the obstacle course.


Cost: Free

Maryland Coast Bike Festival

Maryland Coast Bike Festival

OCEAN CITY, MD – Three bike routes to explore Maryland’s scenic coastal region: 18.5 miles to Assateague Island, 38 miles through Maryland’s Coastal backcountry, Metric Century to Assateague Island and through backcountry. 


Cost: $35, $55 & $65, depending on which ride

Tour de Chesapeake bike ride

Tour de Chesapeake

MATHEWS, VA – Scenic cycling with flat routes and views of the water, local eats, toe-tapping music located on Virginia’s Middle Peninsula. Multiple route choices and free onsite campaigning available. 

MAY 20

Cost: $40, online registration closes May 9, walk registration allowed


Neavitt, MD, pier

Tour de Talbot

EASTON, MD – Ride throughout Talbot County, one of the most scenic cycling areas on Maryland’s Eastern Shore. Those among a 30-, 40-, or 62.5-mile (metric century) ride. It starts at the Easton fire hall. 


Cost: $50, includes ferry fee

Bikes & Beers start in Baltimore

Bikes and Beer: Union Craft Brewing

BALTIMORE – Union Craft Brewing hosts this 15, 30 and 50-mile ride through Baltimore on bike trails in parks and parkways snaking throughout the city, with some routes along historic neighborhood streets. 


Cost: $80 ($55 early registration) for shorter rides, $90 ($65) for longer rides

Tour de Frederick bike ride

Tour de Frederick

FREDERICK, MD – Ride scenic Frederick County through farmland, covered bridge and historic towns with a choice of four routes: 100-, 62-, 31-, and 10-miles. Long route goes through Catoctin Mountain Park. This is one of the few with a 10 mile ride. 


Cost: $15 – $100, depending on ride. Also, cheaper if you register early.

Bay to Bay bike ride in Maryland

Bay to Bay Ride

BETTERTON, MD – The tour consists of five routes between 26 and 102 miles in length. The flat loop routes take in the scenery of the heartland of the Upper Eastern Shore of Maryland and Delaware including farmlands, old country homes, quaint towns, and great country stores


Cost: $50 ($35 early registration)


Heart of Chesapeake Bike Ride

Heart of the Chesapeake Bike Tour

CAMBRIDGE, MD – Ride through Blackwater National Wildlife Refuge and Vienna, MD, on the Nanticoke River. Rides: 65 miles, 52 miles or 32 miles. 


Cost: $70

Bike to Beach ride for autism

Bike to the Beach

WASHINGTON, DC & BALTIMORE – Groups start from either DC or Baltimore and ride to Dewey Beach, Delaware, then take a bus back after the 100 mile ride. Hugely popular ride. 

JULY 28 (a Friday)

Cost: $50-$500 depending on which level you choose


Covered Bridge bicycle ride through Lancaster, PA

Covered Bridge Classic

LANCASTER, PA – This is a unique ride. The 100-, 65-, and 35-mile routes through Lancaster County take you through covered bridges and by Amish farms. How many covered bridges? Depends on the length of the course. All routes cover rolling terrain with moderate climbing in and out of Pennsylvania valleys on the longer rides. It can be a challenge.


Cost: about $45 for early registration and goes up to about $65

Iron Furnace Fifty bike ride in Maryland

Iron Furnace Fifty

SNOW HILL, MD – Ride through rural Lower Eastern Shore of Maryland on 50K, 50 Mile, and 100K routes among woods and farms.


Cost: about $60, cheaper with early registration


Civil War Century Bike Ride

Civil War Century

THURMONT, MD – Five rides ranging from long and mountainous to short and rolling. The climbs range from relatively easy 970 feet to a very difficult 7,000 feet. This is limited to 1,600 riders and sells out. 


Cost: $70

DC Bike Ride Cyclists in front of MLK Monument

DC Bike Ride

WASHINGTON, DC – This 20-mile ride goes past the monuments and historic sites in the nation’s capital and finishes with a festival in front of the U.S. Capitol.


Cost: $60+, cheaper with early registration

2014 Choptank Heritage Skipjack Race.

Skipjack Bike Tour

DEAL ISLAND, MD – A ride across the flats of Deale Island Historic District and Deal Island State Wildlife Management Area. The ride is part of the annual Deal Island-Chance Volunteer Fire Company annual fundraiser, Skipjack Races.


Cost: $30

Rural waterway

Ride for Clean Rivers

WYE MILLS, MD – Ride the beautiful back roads of Talbot and Queen Anne’s counties on Maryland’s Eastern Shore. Choose from 20-, 35-, or 62-mile routes. 


Cost: $50


Cycling through Annapolis, MD

Lifeline 100 Century Ride

MILLERSVILLE, MD – This is a ride through Anne Arundel County which includes Annapolis, Severn River, BWI and country roads. Choose 65-, 30-, and 15-miles. This can be hilly, but you’ll feel like you’re riding everywhere. 


Cost: $25-$50, depending on which ride

Seagull Century bike ride

Seagull Century

SALISBURY, MD – Seagull is the grand finale of the Maryland cycling season. Two routes: 100 miles to Assateague State Park (the one with wild horses at the ocean) and 65 miles to Cypress Park. Limited to 5,000 riders. 


Cost: $100 (early), $130 (later), registration opens June 1