Cookie Classic Run
About this race
It's our 13th Annual Cookie Classic Run!
January 16th, 2027, Saturday 9am 1246 Dismal Swamp Canal Trail
This multi-distance family friendly run/walk event is a great way to launch the 2027 cookie season & start runners off on their 2027 running year! All distances are out and back, on flat asphalt at Chesapeake's Dismal Swamp Canal Trail, with Girl Scout Cookies waiting for you at the finish! Whether you're an experienced runner or just starting out, this is the perfect opportunity to challenge yourself, meet new people, and have fun! All abilities welcomed. We can't wait to see you at the starting line!Distance Categories: 1 mile, 5k, 10k
Virtual Run – “Do-Si-Don't Show” Challenge – “Conquering The Cookie” Run Perks:- Box of Cookies - Register by 10/16/2026 for guaranteed selection of a box of cookies provided after you’ve completed your distance in person
- Race Shirt - Register by 11/1/2026 for guaranteed T-shirt sizing
- Chipped timing
- Photos - Access to professional photographs (digital images available at no fee)
- Digital Finisher certificates
- All 1 mile runners Receive Commemorative Patch
- All 5k & 10k runners Receive Finisher Swag & Medal
- 5k Age Placement Awards
- 10k Age Placement Awards
- DJ & Warm Up Session
- Do-Si-Don't Show Virtual Runners receive the finisher gift(s), medal, T-shirt & race bib delivered by post. (Virtual does not receive a box of cookies.)
- Conquering the Cookie Event Series: Earn Bling Finisher Gift by completing challenge running events. This is a 2-part in-person only run challenge; Runners complete 1 distance in Chesapeake VA then 1 distance in Troutville VA)
- 5k Water Stations
- 10k Water & Gatorade Station
- Start/ Finish Porta-potties
Cookie box choice & T-shirt size are not guaranteed and subject to availability on a first come, first serve basis or until quantities last if not registered by guaranteed deadline dates listed. Quantity updates and availabilities are provided at registration.
Please note Pets or Comfort Animals of any kind are not permitted on course unless they are ADA-compliant certified service animals.
The Cookie Classic Run is a celebration of Girl Scouts, Girl Scout families, and those who support the Girl Scout mission of building Girls of Courage, Confidence, and Character who make the world a better place!
For questions, please contact the Cookie Classic Committee at: cookieclassic5k@gmail.com
Sign Up Today and Join the Fun!Pick your distance
Running
Cookie Classic Run - Samoa Stroll 1 Miler
Cookie Classic Run Trefoil Trek 5K
Cookie Classic Run - Tagalong 10k
Conquering the Cookie - Challenge
Conquering the Cookie Challenge 2027 🌟 Conquering the Cookie Challenge: Cookie Classic & Tough Cookie! 🌟 Get ready to lace up, level up, and explore more! 🍪🏃♀️ with the Conquering the Cookie Challenge — a double-dose of fun, fitness, and friendship featuring two of our favorite Girl Scout races: The Cookie Classic Run and The Tough Cookie Challenge! Here’s how it works: If you participate in person at both events, you’ll earn an EXTRA-special “Conquering the Cookie” pin 🏅— plus ultimate Bragging Rights for taking on the challenge! To join the series: 1️⃣ Register for each race (at any distance). 2️⃣ Add on the $5 Conquering the Cookie fee. 3️⃣ Crush both races and claim your limited-edition pin at the Tough Cookie finish line! It’s the perfect way to explore more (just like our newest cookie, the Exploremores!) while celebrating your strength, spirit, and the sisterhood of Girl Scouting. 💚 🍪 Cookie Classic: January 16th Dismal Swamp Canal Trail, Chesapeake Any Distance : 1-Miler, 5K, 10K Flat asphalt course Learn More & Register → 🍪 Tough Cookie Challenge Race: March 20th Greenfield Recreation Park Cross Country Course, Roanoke Valley 1-Miler, 5K: hilly trail course Learn More & Register →
Do-Si-Don't Show- Virtual 5k
Typical race-day weather
Based on 4 years of Open-Meteo archive data for this event's race dates in Chesapeake, plus the 3 days either side.
The sun rises at 7:16 AM and sets at 5:13 PM local time (EST) in Chesapeake on January 16, 2027 — 9h 57m of daylight.
Course
No course map published yet.
The organizer hasn't released a route for this event, and we don't publish guesses. If you're the organizer, send us a GPX file and we'll draw the profile.
Reviews
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Results — Cookie Classic Run
Other races near Chesapeake
Different organizers, within 40 miles, in the next three months
Tidewater Strider Dismal Swamp 50K / Marathon /Half Marathon/50K Relay
Tidewater Striders Distance Series #1
Chesapeake Rotary Holly Jolly Jog Race and Fun Run presented by the YMCA of South Hampton Roads
5K Angel Run
🏃 Plan Your Next Race in Chesapeake
Find upcoming events by distance:
- Chesapeake 5K Races 24 races
- 10K Run Events in Chesapeake 3 races
- Chesapeake Running Calendar 2026 31 races
Where this page comes from. Race details were last updated on . We re-check listings regularly and again in the week before race day.
- Entries, prices, waves and inclusions — the event's official registration page
- Temperature and humidity — Copernicus ERA5 reanalysis via Open-Meteo (CC BY 4.0)
- Elevation and terrain relief — Copernicus DEM GLO-90, ESA (CC BY 4.0)
- Comparisons and counts — Race Discovery calendar, 32 Chesapeake events
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