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, US

Camp, Charity Ride, Kids, Recreational, Tour
12–15 Jul 2025
Featured event

SJW Membership 2025

Norma, New Jersey, United States

22 Jan 2025 – 1 Jan 2026

Bay to Bay Jim Gent Memorial Ride 2025

Betterton, Maryland, United States

22 Jun 2025

Pennsylvania Pine Creek Trail & Ghost Town Trail fully-supported Bike Tour

Blairsville, PA , USA

Recreational, Tour
8–11 Jul 2025

New Holland Bicycle Race #2 2025

New Holland, Pennsylvania, United States

Century, Gran Fondo, Half Century, Metric Century, Recreational, Road Racing, Time Trial, Tour
12 Jul 2025

Wild & Wonderful West Virginia Gravel fully-supported Bike Tour

Davis, WV, USA

Gravel Grinder, Recreational, Tour
13–17 Jul 2025

19th Annual Doona Sunderdick Columbia Pedal & Paddle

Columbia, Maryland, United States

13 Jul 2025

2025 Firefighter 50 Bike ride

Westminster, Maryland, United States

Century, Half Century, Metric Century
20 Jul 2025

Easy Rider GAP fully-supported Bike Tour

Ohiopyle, PA, USA

Recreational, Tour
20–22 Jul 2025

Spellbound Century 2025

Mount Holly, New Jersey, United States

Century, Half Century, Metric Century
26 Jul 2025

TheNightMare Tour

Reinholds, Pennsylvania, United States

Adventure Race, Century, Randonneuring, Road Racing, Time Trial, Tour
2 Aug 2025

Pittsburgh to DC: GAP and C&O fully-supported Bike Tour

Ohiopyle, PA, USA

Recreational, Tour
10–15 Aug 2025

Ramapo Ralley 2025

Mahwah, New Jersey, United States

17 Aug 2025

CCAP 5th Annual Benefit Bike Ride

Winchester, Virginia, United States

Recreational
23 Aug 2025

BR2RB Bikeathon

Quarryville, PA

Camp, Century, Charity Ride, Road Racing
5 Sep 2025

2025 Civil War Century

Thurmont, Maryland, United States

Century
6 Sep 2025

C&O Canal fully-supported Bike Tour

Alexandria, VA, USA

Recreational, Tour
14–19 Sep 2025

Breakthrough Challenge

Birdsboro, PA, USA

Charity Ride
14 Sep 2025

Rcdcu Bike to Fight Prostate Cancer

Somerset, New Jersey, United States

Half Century
20 Sep 2025

Jersey Devil Metric Century 2025

Pittsgrove, New Jersey, United States

Metric Century
20 Sep 2025

RCDCU “Bike to Fight Prostate Cancer”

Somerset, New Jersey, United States

Charity Ride
20 Sep 2025

Gettysburg and the Civil War 4 day guided bike tour

Gettysburg, PA, usa

Tour
21–24 Sep 2025

New York Empire State Trail fully-supported Bike Tour

Elizabeth, NJ, USA

Recreational, Tour
21–26 Sep 2025

10th Annual #CaringForRare Cycling Event

Stockton, New Jersey, United States

Century, Charity Ride, Metric Century, Recreational, Tour
21 Sep 2025

The Harvest Hundred

Delaplane, Virginia, United States

Century, Charity Ride, Gravel Grinder, Metric Century, Road Racing
21 Sep 2025

Great Allegheny Passage 4-day fully-supported Bike Tour

Ohiopyle, PA, USA

Recreational, Tour
22–25 Sep 2025

Chesapeake Bay and Maryland Eastern Shore fully-supported Bike Tour

Easton, MD, US

Recreational, Tour
30 Sep – 3 Oct 2025

HABPI’s Ride for Trails – Gettysburg

Gettysburg, Pennsylvania, United States

Charity Ride, Recreational
4 Oct 2025

Adamstown Dirty Dozen Hill Climb

Reinholds, Pennsylvania, United States

Adventure Race, Century, Gran Fondo, Half Century, Metric Century, Recreational, Road Racing, Time Trial
4 Oct 2025

2025 Anne Arundel County Lifeline 100 Bicycle Event

Millersville, Maryland, United States

Century
5 Oct 2025

Lifeline 100

Millersville, MD, USA

Century, Charity Ride, Half Century, Kids, Recreational
5 Oct 2025

Giro del Vino VIII

Hammonton, New Jersey, United States

5 Oct 2025

New Holland Bicycle Race #3 2025

New Holland, Pennsylvania, United States

Century, Gran Fondo, Half Century, Metric Century, Recreational, Road Racing, Time Trial, Tour
11 Oct 2025

Covered Bridges Ride 2025

Erwinna, Pennsylvania, United States

12 Oct 2025

Virginia’s Capital Trail & Williamsburg fully-supported Bike Tour

Henrico, VA, USA

Recreational, Tour
12–15 Oct 2025

STOP, SWAP AND SAVE 2026

WESTMINSTER, Maryland, United States

15–16 Feb 2026

Ocean to Bay Bike Tour

Bethany Beach, Delaware, United States

Century, Charity Ride, Half Century, Metric Century, Recreational
24–25 Apr 2026

Brooklyn 200K 2025

Brooklyn, New York, United States

21 Jun 2026
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