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  • Distance: 14.6 km from Leesburg
    Sun, Oct 25, 2026 at 10:00 AM

    Run the Vineyards race series comes to the prestigious Rocklands Farm Winery in Montgomery County.

    Join us for a scenic 5K run through the vineyard and farm and finish with a relaxing after party at their historic property. Create new memories and traditions with friends and family while enjoying the outdoors, healthy exercise, and wine at the finish line!

    Race Features:

    • Scenic 5K Course with a variety of spectacular views

    • Chip-timed with instant results. Race start time: 9:00 AM

    • Awards for top Overall and Age Group Winners (3 Deep, Male and Female ages (Under 14, 15-19, 20-29, every 10 yr.)

    • Well groomed cross country style course with a combination of hard packed dirt, gravel, and grass trails.

    • Friendly volunteers and hydration stations

    • Professionally well marked course

    • Walkers and children are welcome to participate.1 Hour time limit kindly requested. Need to be registered and start on time at 9 AM behind the runners for safety of all participants.

    After Party:

    • Award Winning Wines available for drinking, tastings, and sales

    • Complimentary drink ticket for a glass of wine for over 21

    • Live Music performed until Noon

    • Food Truck on-site all day for great food options

    • Spacious indoor and outdoor seating areas to enjoy at Rocklands farm

    Swag and Amenities:

    • High-quality Custom Tech shirt in Women's, Men's/unisex, and Youth sizes. Option to upgrade to long-sleeves for $6 extra. *Please register by Oct. 11 to guarantee your first choice. Many extras ordered and are available while supplies last after Oct. 11.

    • Souvenir Wine Glass with the Run the Vineyards logo

    • Souvenir Finisher Medals optional for purchase for $8 during registration or $10 on race day (while supplies last)

    • Free Race Photos and Parking

    • Spectators welcome! Additional wine available for purchase.

    Packet Pick-up on Race Morning from 8:30 - 9:30 AM at "Good Day for a Run" Tent. Race starts at 10:00AM so runners/walkers need to pick up their race packet by 9:30 AM please. Race announcements start at 9:45 AM.

    Volunteers have fun and receive glass of wine & free future race! Visit "Volunteer" tab for details & sign up!

    See full details
    5kGravelIndoorRunTrailWalk via RunSignup
  • Distance: 19.7 km from Leesburg
    Sat, Apr 24, 2027 at 7:00 AM
    Cycling via BikeReg
  • 18045 Central Park Cir, Boyds, Maryland, 20841, United States
    OpenStreetMap Google Maps
    Distance: 21.1 km from Leesburg
    Sat, Oct 10, 2026 at 5:30 AM
    CyclingMountain Biking via BikeReg
  • 44078 Cheltenham Circle, Ashburn, Virginia, 20147, United States
    OpenStreetMap Google Maps
    Distance: 21.9 km from Leesburg
    Sat, Aug 08, 2026 at 8:00 AM

    Swim in the Lakes Rec Center outdoor pool, bike around the neighborhood, and run on a marked course starting and ending at The Lakes Rec Center.

    What do you get for your entry?

    • Well organized and professional event

    • Race T-Shirt

    • Custom Finisher Ribbon

    • Real-Time Results

    • Satisfaction of finishing a multisport race!

    • Meeting other athletes and establishing new friends!!!

    KidsRunSwimTriathlon via RunSignup
  • Little Bennet Regional Park Trailhead, Clarksburg, Maryland, 20871, United States
    OpenStreetMap Google Maps
    Distance: 22 km from Leesburg
    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
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