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  • Distance: 23.7 km from Frederick
    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
  • 12805A Mink Farm Rd, Thurmont, Maryland, 21788, United States
    OpenStreetMap Google Maps
    Distance: 20.1 km from Frederick
    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
  • Little Bennet Regional Park Trailhead, Clarksburg, Maryland, 20871, United States
    OpenStreetMap Google Maps
    Distance: 18.4 km from Frederick
    Sun, Aug 16, 2026 at 10:00 AM

    Welcome to the Little Bennett Dawg Daze MTB race - sponsored by Ocelot Timing and Events. We hope that every participant will have an enjoyable experience in this event. Please keep in mind that the temperatures in August can be very warm. Please hydrate frequently and stop riding if you feel overheated or fatigued. We will have sweepers with nutrition and water during the event. If you have any questions about this race, please reach out to us at [email protected]. Race Notes: Pick up your number plate at the check-in table. Check-in closes at 9:45 AM. You must sign the race waiver online in order to participate. All registration will be conducted through BikeReg. No cash, checks or credit cards will be accepted at the event. There will be a $10 fee for late/day-of entries ( registrations made after 8/13/26 at 5pm). BikeReg fees are included in our registration prices. There will be a mass start at 10 AM for the 180 minute group and a second mass start at 10:05 AM for the 90

    minute group, with a racer meeting at 9:50 AM at the start/finish line. Each racer will complete as many laps as possible in 180+ or 90+ minutes, depending which race you are entered in. Racers are expected to self-support for mechanicals and nutrition for the duration of the race. There will be an aid station/pit area where hydration will be provided. The course is approximately 5 miles in length and fast and flowy. The trails are open to other users such as hikers, runners, cyclists, and horse riders. While we provide advance notice of the race, you may still encounter other users on the course. Please be courteous and pass other trail users carefully. Weather Policy: MNCPP-MC Parks and Ocelot Timing and Events has the discretion to hold the the race depending on weather conditions on the day of the race, as well as current course conditions. If there is wet weather/rain preceding the start, or forecast for race day, we will communicate race status to participants as soon as possible.

    Cancellation Policy: If we are not able to host the race due to regulatory or weather conditions, your registration fee will be refunded less prorated expenses we cannot recover. Directions: The trailhead is located off Prescott Road past the Golf Course. Follow signs and directions to the parking area. https://goo.gl/maps/cfCv4SPGHPXxkiyY8 Course Map ( subject to change): See full course details [DawgDaze_LittleBennett.png] Event Sponsors [3248f054-2f1a-4372-addf-b6b0e2d3cff2.png]

    See full details
    CyclingMountain BikingTrail via BikeReg
  • Frederick Road And East Moser Road, Thurmont, Maryland, 21788, United States
    OpenStreetMap Google Maps
    Distance: 22.6 km from Frederick
    Sat, Sep 19, 2026 at 7:00 AM

    Some of the most beautiful countryside east of the Mississippi!

    • Earn bragging rights on the long and hilly routes of 100 and 75 miles

    • Look at the mountains on rolling terrain across 65- and 50-mile route

    • Enjoy a 25-mile covered bridge tour

    • Fully supported with well-marked routes, Ride with GPS navigation, SAG, and well stocked rest stops

    • End of ride celebration with boxed lunches, festive music, and the popular ice cream truck

    Event details and schedule

    The Civil War Century is an event with five different routes that are designed for different ability levels, from the 25 mile Covered Bridge Quarter Century for beginners and those that don't ride long and hilly rides up to the 100+ mile Civil War Century which is intended for experienced, well trained cyclists that have done at least a couple of centuries already. For the history buff, you can visit Crampton's Gap, South Mountain, Antietam and/or Gettysburg battlefield sites. You'll see all four if you elect to ride the full century.

    Organize your ride crew as a team for a discount! Captain names the team for others to join.

    See full details
    Cycling via Active.com
  • Distance: 12.4 km from Frederick
    Sat, Oct 24, 2026 at 7:00 AM

    [746aa494-2955-4d7d-862d-b77f13a71dd2.PNG]

    Bike Doctor Frederick Grand Fondue

    October 24, 2026

    Presented by Bike Doctor Frederick & Dirty Kitten Productions; Hosted by Orchid Cellar Meadery & Winery; Benefiting Heartly House

    Join us at Orchid Cellar Meadery & Winery on Saturday, October 24th for a casual and fun, yet challenging, ride on a variety of terrain (road/gravel/dirt). The routes begin in Middletown, MD and tour through various parts of Frederick County. Be prepared to ride a mixture of terrain both on and off-road: pavement, gravel, and trail!

    Event entry includes: Custom routes (along with GPS files and cue sheets), stocked aid stations (Half & Grand routes only), event glasses with ONE free drink per participant served at Orchid Cellar following the ride (for participants 21 and over only), ride snacks, live music, and various prizes/giveaways!

    Registration opens May 2026 (prices increase 7/1, 8/1, 9/1, 10/1):

    • Grand Fondue - $50, $55, $60, $65, $70

    • Half Fondue - $40, $45, $50, $55, $60

    • Mini Fondue - $30, $35, $40, $45, $50

    Junior rides U19 receive a $5 discount

    Sorry, NO refunds, transfers, or deferments. All no-show registration fees will be donated to Heartly House.

    Start Time Windows: 7:00-8:30am (Grand); 9:00-10:00am (Half); 10:00-11:00am (Mini)

    *Ride times are “rolling” which means you can start anytime during your designated time slot. This is to spread out arrival for parking and check-in, as well as keep ride groups smaller on the roads. The venue will open at 6:30am (Grand Fondue riders may start as early as 7:00am). Please do NOT arrive earlier than 6:30am

    Location: Orchid Cellar Meadery & Winery - 8546 Pete Wiles Rd, Middletown, MD 21769

    Distance & Elevation:

    • Mini - approx 25 miles & 2,000 ft elevation (moderate)

    • Half - approx 50 miles & 5,500 ft elevation (challenging)

    • Grand - approx 100 miles & 10,000 ft elevation (extremely challenging)

    Terrain (mixed-surface): pavement, gravel, and some optional trail- Road bikes with narrow tires are NOT recommended (at least 32mm and up, treaded tires recommended)

    *ALL route info, GPS files, cue sheets, and maps can be found HERE the week of the event (by Wed PM).

    Aid Stations: Half (50 mile) & Grand (100 mile) routes ONLY (@ThorpeWood Barn - 13002 Mink Farm Rd, Thurmont, MD). The ThorpeWood Barn Aid Station will be open 10am-4pm.

    Support: Pre-Ride bike check & support provided by Bike Doctor Frederick

    Music: Matt Stowell Music will be playing (2-5pm) at Orchid Cellar Meadery

    Food: La Carreta Tacos y Tortas Food Truck will be on-site (12-6pm) or bring your own food

    Drinks: Mead & wine served by Orchid Cellar (absolutely NO outside alcohol permitted)

    Gear Swap: Bring lightly used cycling gear, parts, and accessories to donate or swap/trade (no For Sale items). Leftover items will be donated to a local cycling nonprofit (i.e. Bikes for the World or Phoenix Bikes)

    Medical: Provided by On the Trail First Aid (Wilderness First Aid, Standard First Aid, CPR/AED, Health Care)

    Contacts: Alex & Chris Howell - Dirty Kitten Productions ([email protected]) 240-215-4818; Bike Doctor Frederick ([email protected]) 301-620-8868

    This event benefits Heartly House in Frederick, MD: A non-profit organization that provides services, free of charge, to survivors of domestic abuse, sexual assault, intimate partner violence, human trafficking, and child abuse. Heartly House also works to develop community awareness programs and prevention education in the area. Proceeds from this event will be donated directly to Heartly House. You may choose to make an additional donation during registration.

    See full details
    CyclingTrail via BikeReg
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