Bike Rides in Maryland

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Welcome to your calendar for the best organized cycling events near you. From Century Rides, Gran Fondos, and Charity Bike Rides, to Mountain Bike, or Ultra Distance.
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San Mar’s The Great Bicycle Tour of the Historic C&O Canal

Boonsboro, MD

Charity Ride, Kids, Recreational, Tour
11–14 Jul 2026
Featured event

Bike 4 Haiti

Pittsburgh, Pennsylvania, United States

Charity Ride, Kids, Recreational, Tour
18–25 Jul 2026
Featured event

Gettysburg Fall Cycling Weekend, October 23-24-25, 2026

Gettysburg, Pennsylvania, United States

Century, Half Century, Kids, Metric Century, Mountain Bike, Multisport, Randonneuring, Recreational, Tour
23–25 Oct 2026
Featured event

Firefighter 50 Bike Ride 2026

Westminster, Maryland, United States

Century, Half Century, Metric Century
19 Jul 2026

Spellbound Century 2026

Mount Holly, New Jersey, United States

Century, Half Century, Metric Century
25 Jul 2026

TheNightMare Tour

Reinholds, Pennsylvania, United States

Adventure Race, Century, Gran Fondo, Randonneuring, Recreational, Road Racing, Time Trial
1 Aug 2026

Brake the Cycle of Poverty

Kutztown, PA, USA

Century, Charity Ride, Kids, Recreational
8 Aug 2026

C3 Scatch N Denton

denton , maryland

Gravel Grinder
29 Aug 2026

Ramapo Rally 2026

Mahwah, New Jersey, United States

30 Aug 2026

Willing Warriors 8th Annual Warrior Ride

Broad Run, Virginia, United States

Charity Ride, Gravel Grinder
12 Sep 2026

Milton Harvest Festival 28 Mile Bike Race

Milton, Pennsylvania, United States

12 Sep 2026

Keystone State Ride

Manayunk , PA, USA

Charity Ride, Recreational
13 Sep 2026

CJBC FARMLANDS BIKE TOUR

Manalapan, New Jersey, United States

Century
13 Sep 2026

2026 Civil War Century

Thurmont, Maryland, United States

Century
19 Sep 2026

RCDCU Bike to Fight Prostate Cancer 20th Anniversary Ride

Somerset, New Jersey, United States

Half Century
19 Sep 2026

C3 Rolling Donut Ride

Centreville , maryland

Charity Ride
26 Sep 2026

Breakthrough Bike Challenge

Birdsboro, PA 19508, PA, USA

Charity Ride
27 Sep 2026

Cap to GAP Gravel Trail Adventure

Washington DC

Charity Ride, Gravel Grinder, Recreational, Tour
28 Sep – 7 Oct 2026

Adamstown Dirty Dozen Hill Climb

Reinholds, Pennsylvania, United States

Century, Gran Fondo, Half Century, Recreational, Road Racing, Time Trial
3 Oct 2026

Lifeline 100

Millersville, Maryland, United States

Century, Charity Ride, Half Century, Kids, Metric Century, Recreational
4 Oct 2026

New York Empire State Trail fully-supported Bike Tour

Elizabeth, NJ, USA

Recreational, Tour
4–9 Oct 2026

2026 Anne Arundel County Lifeline 100 Bicycle Event

Millersville, Maryland, United States

Century
4 Oct 2026

Giro del Vino IX

Hammonton, New Jersey, United States

4 Oct 2026

Fitness & Fight 2026

Williamsburg, VA, USA

Charity Ride, Recreational
10 Oct 2026

New York Empire State Trail Bike Tour – fully-supported

Elizabeth, NJ, USA

Recreational, Tour
11–16 Oct 2026

Covered Bridges Ride 2026

Erwinna, Pennsylvania, United States

11 Oct 2026

PA Hope Ride Against Cancer

Marietta, Pennsylvania, United States

Charity Ride
16 May 2027
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