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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East Coast Bike Festival

Berlin, MD

Half Century, Recreational
26 Apr 2025
Featured event

Lymphoma Research Ride

Dickerson, Maryland, United States

Charity Ride, Half Century, Kids, Recreational
27 Apr 2025
Featured event

20th Cap2Cap Ride

Richmond, Virginia, United States

Century, Half Century, Kids, Metric Century
9–10 May 2025
Featured event

C3 tri-county ice cream classic

easton, maryland

Century, Charity Ride, Metric Century, Recreational
10 May 2025
Featured event

Delaware Gran Fondo

Wilmington, Delaware, US

Gran Fondo
18 May 2025
Featured event

Blue Ridge Ride To Defeat ALS

Keswick, Virginia, USA

Charity Ride, Gravel Grinder, Metric Century, Recreational
7 Jun 2025
Featured event

Farmland Ride 2025

Flemington, New Jersey, USA

Metric Century, Recreational, Tour
8 Jun 2025
Featured event

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

New Holland Bicycle Race #1 2025

New Holland, Pennsylvania, United States

Century, Gran Fondo, Half Century, Metric Century, Recreational, Road Racing, Time Trial, Tour
19 Apr 2025

Ride With Rotary – 4th Annual Charity Ride

Front Royal, Virginia, United States

Century, Charity Ride, Metric Century
26 Apr 2025

Hackettstown 200K 2025

East Windsor, New Jersey, United States

3 May 2025

Suburban Cyclists Unlimited Best of Bucks Century

Doylestown, Pennsylvania, United States

Charity Ride, Half Century, Kids, Metric Century, Mountain Bike, Recreational, Tour
10 May 2025

Cycle The Savage

Swanton, Maryland, United States

Camp, Charity Ride, Kids
10 May 2025

Bike Ride of The Historic Dismal Swamp Canal Trail

Chesapeake, Virginia, United States

10 May 2025

C&O Canal fully-supported Bike Tour

Alexandria, VA , USA

Recreational, Tour
11–16 May 2025

Bike to Work Day 2025

Washington, DC , District of Columbia, USA

Recreational
15 May 2025

HERSHEY SPRING CYCLING WEEKEND

Grantville, Pennsylvania, United States

Century, Half Century, Kids, Metric Century, Mountain Bike, Randonneuring, Recreational, Tour
16–18 May 2025

Tour de Chesapeake

Mathews, Virginia, United States

Century, Charity Ride, Recreational, Tour
17 May 2025

Ride of Silence

Chesapeake, Virginia, United States

21 May 2025

Hancock, MD – Blessing of the Bikes

Hancock, MD, USA

31 May 2025

Space Race Rumpus

Green Bank, WV, US

Adventure Race, Camp, Kids, Mountain Bike, Recreational, Road Racing, Time Trial, Tour
6–8 Jun 2025

Tour de Frederick

Frederick, Maryland, United States

Century, Charity Ride, Kids, Metric Century, Recreational, Tour
7 Jun 2025

OutCycling Pride Ride

new york, New York

Half Century, Metric Century, Recreational, Tour
8 Jun 2025

BKtotheBeach

Brooklyn, NY, USA

Century, Charity Ride
8 Jun 2025

Patuxent Oxon Hill Rural Legacy Ride

Upper Marlboro, Maryland , USA

Half Century, Recreational
14 Jun 2025

Tour de Talbot

Easton, Maryland, USA

Charity Ride, Metric Century, Recreational, Tour
14 Jun 2025

Stockton University- G. Larry James Legacy Bike Ride – 17th Annual

Galloway, New Jersey, United States

Charity Ride
14 Jun 2025

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

Ohiopyle, PA, USA

Recreational, Tour
6–11 Jul 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

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

C&O Canal fully-supported Bike Tour

Alexandria, VA, USA

Recreational, Tour
14–19 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

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, Mountain Bike, Recreational
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

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
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