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  • 17901 Halfway Boulevard, Halfway, Maryland, 21740, United States
    OpenStreetMap Google Maps
    Distance: 23.7 km from Thurmont
    Sat, Aug 08, 2026 at 6:30 PM

    The Hagerstown Sprint & Youth Triathlon is a welcoming, community-focused race that brings athletes of all ages together for a fun and competitive day of multisport racing in Hagerstown, Maryland. The Sprint Triathlon offers a fast, approachable course ideal for both first-time triathletes and experienced racers looking to test their speed, while the Youth Triathlon provides a safe, age-appropriate introduction to the sport for kids and teens. With well-marked courses, supportive volunteers, and an energetic race-day atmosphere, the Hagerstown Triathlon celebrates fitness, family, and the excitement of crossing the finish line—no matter your age or experience level.

    All information about this race can be viewed at https://www.rivalraceseries.com/hagerstowntriathlon.

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    10 Miles13 MilesSprintTriathlon via RunSignup
  • Frederick Road And East Moser Road, Thurmont, Maryland, 21788, United States
    OpenStreetMap Google Maps
    Distance: 7.2 km from Thurmont
    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.

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    Cycling via Active.com
  • Distance: 13.4 km from Thurmont
    Sat, Sep 19, 2026 at 8:00 AM

    DetermiNation is the American Cancer Society’s event endurance program, spanning a variety of sports including cycling, running, hiking, yoga, and more. The collective efforts of the dedicated athletes who use their fortitude to help raise funds to take down cancer are nothing short of amazing. When you join DetermiNation, you’re not just participating in an endurance event. You’re pushing yourself to help save lives from cancer. Just like hard work goes into your event training, the American Cancer Society gives it our all through things like breakthrough research, patient programs and services, and a free 24/7 cancer helpline. Together, we’ll tackle every course, rally every community, and stay absolutely relentless in the fight against cancer.

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    CyclingRun via RunSignup
  • Distance: 14.4 km from Thurmont
    Sat, Oct 24, 2026 at 7:00 AM

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    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.

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    CyclingTrail via BikeReg
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