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  • 12805A Mink Farm Rd, Thurmont, Maryland, 21788, United States
    OpenStreetMap Google Maps
    Distance: 16.7 km from Boonsboro
    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
  • 17901 Halfway Boulevard, Halfway, Maryland, 21740, United States
    OpenStreetMap Google Maps
    Distance: 14.6 km from Boonsboro
    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.

    See full details
    10 Miles13 MilesSprintTriathlon via RunSignup
  • Frederick Road And East Moser Road, Thurmont, Maryland, 21788, United States
    OpenStreetMap Google Maps
    Distance: 23.8 km from Boonsboro
    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: 23.7 km from Boonsboro
    Sun, Sep 20, 2026 at 11:59 PM

    Most up to date details available at https://www.granfondonationalseries.com/gran-fondo-maryland

    GRAN FONDO MARYLAND &

    2026 GRAN FONDO NATIONAL CHAMPIONSHIPS

    Presented by

    OURISMAN AUTOMOTIVE GROUP

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    Frederick, MD

    Sunday, September 20, 2026

    CLICK HERE TO ADD TO YOUR GOOGLE CALENDAR

    Gran Fondo National Championships riders start at 8:00AM

    Gran Fondo riders (Gran, Medio, Piccolo) start at 8:30AM

    Benefiting: Linganore Mountain Bike Team (high school team)

    3 Loops to Choose From

    Event Open to All

    4 Timed Sections in the Gran loop – Best Combined Time Wins

    Age Group Categories

    Awards and Winners jerseys for Gran Route Age Group

    Awards & Prizes for 60 mile and 30 mile Age Group winners

    This is a 2026 SENA Gran Fondo National Series event

    Ride with your friends, Race with your friends

    Fully Stocked Aid Stations to keep you going

    U23 Made Possible By Shimano

    Riders who will be 23 years of age or under as of December 31, 2026, are eligible to use the coupon code: U23byShimano at checkout for any of the company’s owned SENA Gran Fondo National Series events including Gran Fondo Florida, Tour of Georgia Gran Fondo, Highlands Gran Fondo, Gran Fondo Asheville, Boone Gran Fondo, Gran Fondo Maryland, as well as the 2026 USA Cycling Gran Fondo National Championships. The offer is limited to participants under the age of 23 and entrants are verified by their age. Juniors – cyclists under the age of 18 – are eligible to use the same coupon code.

    Check-in & Packet Pick Up:

    (Watch for updated Information on these dates and locations the below is from 2025 but will likely be the same)

    Friday from 3:00 PM to 6:30 PM at Ourisman Honda in Bethesda, located at 4800 Bethesda Ave, Bethesda, MD 20814.

    Saturday from 2:00 PM to 6:00 PM at Volvo Cars of Frederick / Audi Frederick located at 6001 Urbana Pike, Frederick, MD 21704.

    Sunday from 6:00 AM to 30 minutes prior to start (7:30 for #GFNats riders, 8:00 for Gran Fondo riders) at 500 Fleming Ave, Frederick, MD 21701 (at location of race start)

    For Gran Fondo Maryland, in order to speed up packet pickup and reduce congestion, riders may collect packets for up to three additional riders. You must present your ID and a copy of each rider’s photo ID and a statement of permission. A text or email containing a photo of a rider’s ID and their statement will work.

    Registration will also be available on Saturday and Sunday.

    Course Description

    After starting in historic downtown Frederick Maryland, the 87 mile Gran Fondo National Series, Gran Route, will gain over 10,000 feet of elevation through several different state parks, municipal forests, protected watersheds, and the Catoctin Mountain National Park. Riders will travel northwest out of the city of Frederick before entering the Frederick Municipal Forest where the first timed section will gain over 1270 feet in a 5.6 mile race segment. At the top riders will be able to relax and enjoy the cool mountain forest as the course plummets over the west side of the mountain range.

    The second timed section ascends the southern approach to Harp Hill for a punchy up-down-up-down-up lasting for a brief 1.4 miles and 279 feet of vertical gain. For the next 25 miles and 2500 feet of cumulative gain, the route then follows a mix of small and obscure backroads heading north towards the decommissioned military base of Fort Ritchie.

    Time Section #3 is a more dynamic segment and certainly cannot be called a timed climb. Section #3 will require riders to use caution and technical skill with several 90° turns including an old bridge crossing and tarp & chip road surface. The section starts on a wide downhill roadway where for the first 4.9 miles riders lose 500 feet of elevation before hitting the last 1k and 300 vertical feet to the finish of section #3 on top of Hornets Nest Road. Time segment #3 known as The Gully of Darius is a total of 5.5 miles -574 /+386 feet. From here the route heads south and works its way back exploring nooks and crannies in the Catoctin Mountain Range and travels through Catoctin Mountain National Park for 22 miles and +2250 feet of untimed pedaling. Past riders will be able to take special appreciation as they descend Park Central Road, which was used in the opposite direct as race section #2 in past years.

    As Gran Route riders approach mile 71 they need to take in a deep breath, shake out their legs and prepare for the hardest segment of the day, (this segment also counts as a time segment for Medio Route riders). Section #4 is 11.4 miles +1203 feet and will test every rider’s ability! The segment starts by gaining 784 feet over the first 4.6 miles and then continues for a challenging and undulating 6.8 miles on top of the mountain ridge on Gambrill Park Road through Frederick Watershed and into Gambrill State Park. After completing time section #4, riders will have over 1000 feet of elevation on their side as they drop off the mountain range and into the valley towards the finish, but completing the route in not over, there are still some hills that are sure to make riders know they are still alive. Riders will return back into historic downtown Fredrick and be welcome to well deserved festivities at the finish line, complete with great food, beverage, and more fun.

    Visit Frederick welcomes you to hip and historic Frederick County, MD. Below you'll find information about hotels and ways to make your stay in Frederick enjoyable and memorable.

    https://www.visitfrederick.org/gran-fondo/

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    See full details
    CyclingGran FondoMountain Biking via BikeReg
  • Distance: 11.3 km from Boonsboro
    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.

    See full details
    CyclingTrail via BikeReg
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