This is a list of Other Supported Rides that are popular with our members. These OSRs will be posted on our Club calendar in 2026 as information becomes available to us. Let us know if an event needs to be added here and to our calendar.
The volunteer to maintain this list is Jim Black.
https://www.bikesignup.com/Race/MD/Easton/PositiveStridesSpringClassic| Ride Name, Alphabetical Sort | Date / Comment | Website Link |
| Amish Country Bike Tour - Dover, DE | 9/19/2026 | https://www.bikede.org/amish-country-bike-tour/ |
| Armed Forces Cycling Classic - Challenge Ride - Washington DC. | 5/30/26. Pros on 5/30/2026 & 5/31/2026 | https://www.cyclingclassic.org/challenge-ride |
| Bethany Ocean to Bay Bike Tour | 4/24-25/2026 | https://oceantobaybiketour.com/ |
| Bikes & Beers Frederick | 4/18/2026 | https://www.bikesignup.com/bikesandbeers-frederick |
| Bikes & Beers Baltimore | 5/30/2026 | https://www.bikesignup.com/bikesandbeers-baltimore |
| Bikes & Beers Kent Island |
7/11/2026 | https://www.bikesignup.com/bikesandbeers-kentisland |
| Civil War Century - Thurmont | 9/12/2026 | https://www.civilwarcentury.com/ |
| Doublecross Metric - Smyrna, DE | 6/x/2026 | https://whiteclaybicycleclub.org/events/doublecross/ |
| FestiVelo - Walterboro, South Carolina | 11/x/2026 4 days | https://festivelo.org/ |
| Firefighter 50 & Century - Westminster, MD | 7/x/2026 | https://www.firefighter50.com/ |
| Five Boro Bike Tour - New York City | 5/3/2026 | TD Five Boro Bike Tour - Bike New York |
| Garrett County Gran Fondo | TBD - ride may not happen | https://garrettcountygranfondo.org |
| Gran Fondo Maryland | 9/20/2026 | https://www.granfondonationalseries.com/gran-fondo-maryland |
| Icicle Metric Century | 4/11/2026 | http://www.whiteclaybicycleclub.org/events/icicle-metric/ |
| Lancaster Covered Bridge Classic - PA | 8/16/2026 | https://coveredbridgeclassic.com/ |
| Lifeline 100 - AA County | 10/4/2026 | Lifeline 100 Ride |
| Lions Bay to Bay Century - Betterton | TBD (4th Sunday in June) | Chestertown Lions Club |
| Maryland Coast Bike Festival - Ocean City | TBD - Spring 26 | https://marylandcoastbikefestival.com/ |
| M2M - Air Force Heritage Memorial to Memorial Ride 4 days from Kitty Hawk to Pentagon | 9/10/2026 - 9/13/2026 | https://afcycling.com/m2m-ride/ |
| Parvilla Bike Shop weekly rides | Thursdays at 5:45pm | https://www.parvillacycles.com/articles/thursday-bikes-and-beers-ride-and-other-events-pg60.htm |
| Patuxent River Rural Legacy Ride | TBD | Click here |
| Positive Strides Spring Classic | 4/11/2026 new | https://www.bikesignup.com/Race/MD/Easton/PositiveStridesSpringClassic |
| Pumpkin Ride (The Great Pumpkin Ride) - Warrenton, VA | 10/x/2026 | https://www.bikereg.com/great-pumpkin-ride?nc=1 |
| Ride for Clean Rivers - Wye, MD | 9/x/2026 | https://www.shorerivers.org/event/rideforcleanrivers2025 |
| Ride for the Feast - Easton | 5/9/2026 | https://www.mfeast.org/rideforthefeast/ |
| Ride of Silence - Annapolis | 5/20/2026 - always the third Wednesday in May | https://www.rideofsilence.org/locations-domestic.php?s=MD |
| Ride to End Hunger - Calvert | 4/x/2026 | https://endhungercalvert.org/bike-ride/ |
| Rolling Donuts - Centerville | 9/26/2026 | Click here |
| Savage Century - Newark, DE | 10/3/2026 | https://whiteclaybicycleclub.org/events/savage/ |
| Seagull Century - Salisbury | 10/3/2026 | https://seagullcentury.org/ |
| Shorefire Century, Middletown, DE | 8/x/2026 | https://whiteclaybicycleclub.org/events/shorefire/ |
| Six Pillars Century - Cambridge | 5/9/2026 | https://www.bikesignup.com/Race/MD/Cambridge/SixPillarsCentury |
| Storming of Thunder Ridge - Virginia | 5/17/2026 | https://www.ymcacva.org/storming-thunder-ridge |
| Three Creek Century - Harrisburg | 9/20/2026 | Event link - Harrisburg Bicycle Club |
| Tour de Chesapeake - Matthews County, VA | 5/16/2026 | tourdechesapeake.org/ |
| Tour de Frederick | 6/6/2026 | https://www.tourdefrederick.com/ |
| Tour de Talbot - Easton | 6/6/2026 | https://tourdetalbot.org |
| Tri-County Ice Cream Classic - Eastern Shore | 5/2/2026 | https://www.ridec3.org/tri-county-ice-cream-classic |
Other Resources
The Bike Maryland calendar, which may include the Chestertown bicycling weekend, St. Mary's Century, Wild Goose Chase Womens ride, and more...
Updated by JMB 9 January 2026 & JCT 1/12/26