Maryland · Saturday, May 9, 2026
The Gunpowder Trailfest is a 5k, 12.5k, 25k, and trail running event held on Saturday, May 9, 2026.
Run the vines in 2026 and join us at one of our most popular summer races, hosted by Charm City Run and our friends at Boordy Vineyards! Not only will registrants enjoy a beautiful golden hour run through the vineyard and surrounding area, but each participant will receive a soft short sleeve shirt and a souvenir wine glass (with a complimentary fill for registrants 21+). Kick back and relax after the race with your hard-earned glass of wine, live music, snacks, and food trucks. Register now to save your spot. We look forward to seeing you!
Welcome to the 19th Annual Jessica Meredith Jacobsen Memorial 5k & Fun Walk! For nearly two decades, our community has gathered every September to turn a tragic loss into a powerful legacy of support. Whether you are chasing a personal best or enjoying a morning stroll with the family, your footsteps directly support the House of Ruth Maryland, ICS Tuition Assistance, and Father O’Neill Charities.
The race and walk will begin at our host school, Immaculate Conception School, in Towson, MD, at 8:00 AM. The race and walk will follow the same course as last year. We will also include a virtual race option for all participants who prefer the flexibility of participating when and where it is convenient for them.
T-shirt and bib pickup will be on September 17th and September 18th at the Knights of Columbus Hall located at 616 W. Seminary Ave, Lutherville, MD 21093, between 3:00-7:00 PM.
Free parking for the event will be available in the garage on Ware Ave. on race day.
Online registration for the 5K and Fun Walk will close at 8:00 PM on 9/18/26. Limited race day registration on 9/19/26 will be available until 7:30 AM. After this time, we cannot guarantee your registration. If you would like to donate to the race, donations will be accepted after 9/19/26.
T-Shirt: A t-shirt with the Knight logo is guaranteed for those who register by September 5, 2026. Registrations after this date will not receive a t-shirt.
Awards: Cash prizes of $100, $50, and $25 for the top 3 female and male overall finishers. Age group medals will be awarded to the top male and female finishers.
Please support the sponsors of our race: T Rowe Price, Mariner Finance, JA Healthcare Services, Verdence Capital Advisors, Hollenshade's Auto Service, Notre Dame Prep, and David Ross Orthodontics.
To learn how to become a sponsor of the race, please email Dan Yardley at [email protected]. There are multiple levels, with various rewards for each level. Sponsorships are tax-deductible when paid to Fr. O'Neill Charities directly. To make a tax-deductible donation, please mail a check made out to Fr. O'Neill Charities to P.O. Box 52, Lutherville, MD 21094-0052. Registrations and donations are not tax-deductible.
Share your photos or videos on our Facebook page (https://www.facebook.com/JMJ5K) of your memories of Jessica, photos of you completing your run or walk, or showing off your race t-shirt!
Adam was one to always lend a hand so in his name we are supporting those in recovery!
Adams Light, Inc. is a 501c(3) charity supporting men and women in recovery
Please register by 8/15 so you can be sure to receive a shirt in your choice of size. Those registering 8/16 and after are not guaranteed a shirt.
Faster Bastards started as a name on a Ragnar relay bib and became Baltimore's biggest free running group. Founded in 2012, the crew has been pounding the city's streets with a singular mission: get faster or die. Built on gritty determination and relentless improvement, Faster Bastards welcomes runners of all levels into a tight-knit community that doesn't just talk about speed, it demands it. Their philosophy attracts a tribe united by the same drive. Two signature runs anchor the weekly rhythm: the Saturday Classic at Canton Waterfront Park and Wednesday to the MAX at Druid Hill Park's William Wallace Statue. What began as a relay team name evolved into a movement that defines Baltimore running culture.
R.I.O.T. Squad Running launched in Baltimore in 2015 when Army veteran Rob sought to manage PTSD through running. What started as solo miles transformed into something profound when friends joined him on the road. Today, this tight-knit family of 25 athletes runs on a simple but powerful philosophy: Running Is Our Therapy. The crew believes movement is medicine, especially for the Black community in Baltimore City. Every run becomes a shared act of healing, with Baltimore's streets serving as the backdrop for community, accountability, and forward momentum. R.I.O.T. Squad Running proves that running transcends the physical, weaving together purpose, belonging, and transformation.