Skip to main content

Cycling events nearby

  • San Mar's The Great Bicycle Tour - TGBT XXXIX
    Boonsboro, Maryland, 21713, United States
    OpenStreetMap Google Maps
    47.6 km from New Windsor
    Sat, Jul 11, 2026 at 12:00 AM

    A fully supported four-day ride on the C&O Canal. Join us for a family-friendly cycling adventure from Cumberland, MD to Mile Marker 0 in Washington, DC. 184.5 miles of no hills, no headwinds and no cars. Plenty of food, lots of support, ride at your own pace, well organized. This is the 39th annual benefit ride for San Mar Family and Community Services, a 501(c)3 nonprofit that maintains national accreditation and has provided services to children, families, and the community every day since November 8, 1883! Learn more about our important work online at sanmarhope.org.

    THE RIDE INCLUDES

    • Transportation by charter bus from Boonsboro, MD to the start of the C&O Canal

    • All meals and snacks

    • Free parking for your vehicle throughout the event at the San Mar campus

    • Rest stops every ten to fifteen miles

    • Camp fees paid for the first two nights or transportation to nearby hotels

    • Hotel on the third night

    • Transport of all gear throughout the event

    • TGBT keepsake t-shirt

    • Return to your vehicle by charter bus from Georgetown at the end of the event

    • A lifetime memory

    This ride benefits San Mar Family & Community Services. All registered riders commit to raising a minimum of $550 for the 4-day ride. Other minimums for weekend only or virtual participation are detailed at the Event Info tab.

    See full details
    96.5 Miles184.5 MilesCyclingVirtual via RunSignup
    sanmartgbt.org Register at runsignup.com
  • 20th Annual Donna Sunderdick Columbia Pdeal & Paddle
    5659 Cedar Lane, Columbia, Maryland, 21044, United States
    OpenStreetMap Google Maps
    40.8 km from New Windsor
    Sun, Jul 12, 2026 at 7:00 AM

    This is a 45 mile biking event through all 10 Columbia Villages. You will also stop at 23 Columbia Association pools along the way to swim a couple of laps (however many you do is up to you). You can slide down the pool slides (if they are open) and take a dive. The ride is supported with 2 food stops along the way and technical support.

    We can honestly say there is no event like this anywhere else!!! Please join us to benefit the Ulman Foundation.

    Event details and schedule

    On-site Registration and Check is starts at 6:30 am. Depending on number of participants, we may stagger the start. Be prepared to start at 7:15 am. Payment for day of event registration must be cash or check. We do not accept credit cards on Ride day.

    There is no rain date. In the event of weather cancellation, we will donte proceeds to the charities and hope for better weather next year.

    Parking is at the pool (please respect the roped off areas), Swansfield Elementary School and on the street.

    Remember that you will be getting wet. A towel is up to you. But DO remember the Sunscreen!!!

    Event FAQ available on our Facebook page.

    See full details
    Cycling via Active.com
    facebook.com Register at active.com
  • Firefighter 50 Bike Ride 2026
    2030 South Pleasant Valley Rd, Westminster, Maryland, 21158, United States
    OpenStreetMap Google Maps
    11.3 km from New Windsor
    Sun, Jul 19, 2026 at 6:00 AM

    Please join in for our annual Firefighter 50 Bike Ride. You will cycle through the beautiful countryside of Carroll County, Frederick County, MD and Adam's County, PA. All 5 fully supported rides start and finish at the Pleasant Valley Fire Company. An all you can eat lunch is included with your registration.

    Event details and schedule

    Event Details:

    • registration begins at 6:00am

    • show and go at 6:00-9:00am

    • special "all you can eat" lunch is served from 11am to 5pm

    • fully supported rides SAG/Sweep/Rest Stops until 4pm

    Recommended Latest Start Times:

    • Century 6:30am

    • Metric Century 7:30am

    • Half Century 8:00am

    • Recreational Ride 8:30am

    • Sweet "16" Ride 9:00am

    See full details
    Cycling via Active.com
    fireifghter50.com Register at active.com
  • Columbia Association KIDS Triathlon
    6400 Martin Rd, Columbia, Maryland, 21044, United States
    OpenStreetMap Google Maps
    44.5 km from New Windsor
    Sun, Jul 19, 2026 at 8:00 AM

    The Columbia Association KIDS Triathlon is a race for all level athletes. Staged at Clemens Crossing Pool in Columbia, MD, participants will complete a pool swim, road bike and paved trail run. The bike course is moderate in elevation change and the run course is relatively flat. Registration includes t-shirt and finisher medal. This race is sanctioned by USA Triathlon. Additional race information can be found at www.rivalraceseries.com/columbiakidstriathlon.

    7-8 YRS OLD

    Swim - 50 yards, Bike - 2 miles, Run - .5 mile

    9-10 YRS OLD

    Swim - 100 yards, Bike - 2 miles, Run - .5 mile

    11-12 YRS OLD

    Swim - 100 yards, Bike - 4 miles, Run - 1 mile

    13 -15 YRS OLD

    Swim - 150 yards, Bike - 6 miles, Run - 1 mile

    See full details
    2.5 Miles5 Miles7 MilesKidsRunSwimTrailTriathlon via RunSignup
    rivalraceseries.com Register at runsignup.com
  • The Shed Enduro
    12805A Mink Farm Rd, Thurmont, Maryland, 21788, United States
    OpenStreetMap Google Maps
    33.1 km from New Windsor
    Sat, Aug 01, 2026 at 6:00 PM

    Welcome to

    The 2026 Shed Enduro

    and

    The Sprint Enduro at The Shed

    all race and volunteer information is available on our website:

    shedenduro.com

    If you need assistance, [email protected] or DM @the_Shed_enduro.

    CyclingEnduroMountain Biking via BikeReg
    shedenduro.com Register at bikereg.com
Cycling events nearby →
Like Wikipedia, anyone can contribute. Sign up to add your local organizations.