The Heartbreak Hill 5k is a 3.1 mile run/walk that takes place on the Hagerstown High School cross country course. This race is one in a series of 8 races that make up the Wayne County Challenge. Each race within the challenge raises money for a charity of their choice and helps promote healthy living and fitness in Wayne County. This race not only attracts members of Wayne County's running/walking community, but also members from the surrounding counties as well. All proceeds from the Heartbreak Hill 5k will go to the Hagerstown High School Athletic Department’s cross country program and the Hagerstown Athletic Hall of Fame.
Event details and schedule
Saturday,
August 8, 2026
Registration begins at 8 a.m.
Registration closes at 8:45a.m.
5K Run/Walk begins at 9 a.m.
The event will take place at the Hagerstown Junior/Senior High School cross country course.
Registration and the starting line are located on the south side of the high school, near the softball diamond.
The entry fees are:
$25 per person if pre-registered by July 31, 2026
$30 per participant the day of the race
All participants will be classified according to age. An awards ceremony and refreshments will follow the race at the site of registration (or in the cafeteria in case of rain). All entrants will also receive a t-shirt (included in the race entry fee) while supplies last. No guarantee on t-shirts without pre-registration.
Welcome back for the 5th annual HW6!
HW6 is a fundraiser for the Hueston Woods Trail Crew.
RACE TSHIRTS HERE Proceeds go to the trails
Directions: Google will give directions to "Hueston Woods Mountain Bike Trailhead". That will take you to the race start and staging.
Race Start: 9:00 am
Race End: 3:00 pm No laps finished after 3:00 pm will count.
Mandatory Pre-Race Meeting: 8:30 am
Number plate pick-up: We will be out there by 7:30am
Prizes: There will be no cash prizes in order to keep the race entry fees cheap! You are racing for pride and glory only. All money that is not used to pay for race insurance, tape, timing, etc. will be donated to the Hueston Woods Trail Crew so we can continue to keep Hueston Woods an incredible mountain biking destination.
Course: The race course will stay on the North side of the park. The course is approximately 8.7 miles long. Start at the mountain bike trailhead ride up the hill, cross the service road and complete the North Loop and the North Loop extension. The course will then cross the service road again and complete the Monkey trail to the finish. https://www.strava.com/segments/26615049?fbclid=IwY2xjawJKZ_9leHRuA2FlbQIxMAABHZxXokKWC93nLztzyfZk0lGQDmt4Ns29DZ2seGPJ3D9AXnWbnsVeDPwHxw_aem_Xw2GwkNxkXf6BLKhOv_a0w
No Food Onsite: There will not be any food onsite. Please prepare accordingly.
Water: There is a water spigot for drinking water.
BYOB: Stay and build community after the race!
Free Camping: There will be free camping for those who wish at the race start. There are no water or electric hookups. There are privy toilets.
Other accommodations: Hueston woods state park offers camping and a lodge. There is also a pool and a lake beach.
Join us for our 4th annual aMAZing 5k trail run at the beautiful Garber Nature Center. Due to the increasing participation, we're now giving awards to the top male and female finishers of each 10-year age group. Walkers are also welcome. All proceeds go to the Friends of the Preble County Park District.
Registration for $35 includes a t-shirt. Children 12 and under are only $25 with a registered adult. If you don't want a shirt, pick the no-shirt option and save $10.
Where: Start/Finish @ Veterans Memorial Park, Remembering Veterans Dr. Ricmond IN parking available at Starr Gennett, 203 E. Main and 50 S. 2nd street
Course: Out& back on Cardinal Greenway https://www.mapmyrun.com/routes/view/6752233459/
Proceeds support WCC & Main Street Richmond
Event details and schedule
When: Sept. 19th 8:45 registration closed, 9am start
Where: Start/Finish @ Veterans Memorial Park, Remembering Veterans Dr. Ricmond IN parking available at Starr Gennett, 203 E. Main and 50 S. 2nd street
Course: Out& back on Cardinal Greenway https://www.mapmyrun.com/routes/view/6752233459/
Proceeds support WCC & Main Street Richmond
To avoid online processing fee, you can mail or deliver your completed registration form:
At the top of this page, click "2026 Mail-in Form."
The form is a fillable .pdf, so you can type right into it!
Print your completed form and mail/deliver to the Darke County Foundation.
$20 if registered by Sept. 9 (includes shirt)
$15 age 0-14 if registered by Sept. 9 (includes shirt)
$5 age 0-14 (no shirt)
$25 after Sept. 9 (limited shirts available)
The Sunshine 5K Run/Walk in beautiful Greenville City Park supports several local non-profit organizations.
The scenic course winds through the park and over the swinging bridge.
Shorter Option Available - 1 Mile Run/Walk for those who want a shorter route (no awards)
Included with your registration:
Quality t-shirt (Register by Sept 9 to guarantee a shirt)
Quality door prizes
Homemade cookies
Variety of fruit and drinks
Swag bag with snacks and other goodies (while supplies last)
Age-group awards for 5K (10 & Under, 11-14, 15-19, 20-24, 25-29, 30-34, 35-39, 40-44, 45-49, 50-54, 55-59, 60-64, 65-69, 70-74, 75+)
Proceeds benefit:
Team AddieGirl for Cancer Association of Darke County
DeColores Montessori School
Edison College Foundation
Final Bow Center for Children's Performing Arts
Darke County Pregnancy Help Center
LifeWise Academy - Greenville
Family friendly 4 hour adventure race with trails, mountain biking, and canoeing at Prairie Creek Reservoir.
MOUNTAIN BIKING IS ENCOURAGED, BUT OPTIONAL.
Kids 12 and under race FREE!
Ages 13-17 are $50.
Each group needs to have at least one person OVER 18. If this doesn't fit your team, contact the race directors and we can discuss options with you.
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Ride Presented by
Cincinnati Cycle Club Foundation
Join us for the 15th anniversary Great Pumpkin Roll Ride on September 26, 2026
This is the Brookville’s BIGGEST ANNUAL RIDE, and we roll out the orange (fall) carpet!
In 2025 We hosted cyclists from 12 states, plus Ontario Canada and everyone loved the routes and amazing fresh homemade finish line food made by Third Place Tavern & Event Center.
Make a weekend of it!
Cyclists can take part in routes ranging from 30 to 63 miles that begin and end at Third Place in Brookville. From the fall colors that decorate the region to the historic Village of Spires in Oldenburg, Ertel's winery stop, and even the covered bridge in Enochsburg, we are so excited to welcome everyone to enjoy our event. Stay post ride for a super tasty freshly made hot post ride meal included in your registration!
It's a perfect weekend getaway as it's also Brookville's German Fest as well as the Antique Machinery Show that weekend.
The ride is fully supported with three super-stocked rest stops. After the ride, dig into a hot post ride meal included in your registration.
There are three ride distances of 30 mile, 50 miles, and a 63-mile metric route.
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free Great Pumpkin Roll Ride cycling socks for registered participants.
cool rider packets at registration
Fully stocked rest stops
Infinit Nutrition hydration at all rest stops
On route support (SAG)
Ride with GPS route downloads
Pre-ride fresh pumpkin rolls from Schmidt Bakery in Batesville, coffee, and juice
Fabulous hot freshly made catered post ride meal by Third Place Tavern and Event Center
bike through the beautiful Village of Spires in Oldenburg
pedal past the oldest Bar in Indiana
covered bridge in Enochsburg
make it a weekend and enjoy Brookville’s Germanfest weekend and the Antique Machinery Show
Event Proceeds benefit the Whitewater Canal Trail, TRAM Food Pantry, and the Cincinnati Cycle Club Philanthropy Foundation
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Ride with GPS route maps:
34.7 Mile Route – https://ridewithgps.com/routes/48493047
50 Mile Medium Route – https://ridewithgps.com/routes/48493170
63.6 Mile Metric Century Route – https://ridewithgps.com/routes/48493286
Day-of registration opens 7:00 am
The 50 and 63 mile metric century routes roll mass start at 8:30am.
The start for the 34 mile ride is at 9:30am.
Early Packet pickup
Friday, September 25, 2026 from 6 to 8 pm
Third Place Tavern and Event Center
734 Main St., Brookville, IN 47012
Ride Pricing
Earlybird registration $55
March 30 - June 29 $60
June 30 – August 30 $70
August 31 – September 26 $75
Day of Registration $85
We will design new super cool new Great Pumpkin Roll Ride jerseys for 2026! Last day to pre-order a jersey is July 20, 2026. (2025 jersey shown)
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Some Fun Pictures from a previous ride!
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Thank you to our wonderful ride sponsors.
Platinum Sponsor
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Gold Sponsors
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Bronze Sponsors
Cincy Builders Services LLC
Sprint and Olympic distance Triathlon, Duathlon, Aquabike, and Relays. High school, Clydesdale, and Athena divisions as well in the Triathlon. Held at Prairie Creek Reservoir Park outside of Muncie, IN with 40+ years of triathlon racing history. Great venue with quiet roads with mild rollers, huge beach and water with beach house, finish in the shaded park, and ample parking near transition. Plenty of hotels+dining in and around Muncie. Finisher medals, race t-shirt, + overall and age group awards Sprint Tri - 500 yard lake swim; 12.5 mile bike; 3.1 mile Olympic Tri - 1650 yard swim; 25 mile bike; 6.2 mile run See all of the 'Ruble Racing' 2026 events at --> www.ruble.racing Follow us on facebook for updates all season - Facebook if you'd like to register for 3 or more events at once contact [email protected] for a discount code to do that Event details and schedule See www.ruble.racing for event schedules
The CCS 5k runs through the beautiful Glen Miller golf course. Please come support CCS students and staff.