The Cookie Classic Run kicks off at 9:00 AM on January 16, 2027, giving you a reasonable morning window to settle into Chesapeake, Virginia before racing. Held at Dismal Swamp Canal Trail, the event offers three distances: a 1-mile option, 5K, and 10K, so you can choose based on your training phase or recovery needs. Entry fees range from $5 to $65 depending on your selected distance and registration timing. If travel plans fall through or weather becomes a factor, the race also provides a virtual participation option, allowing you to complete your chosen distance on your own schedule. With early-morning timing and multiple distance choices, this January race works well for runners testing fitness early in the year or those targeting a low-key tune-up event before spring racing.
From the Race Organizer
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) Course Support: 5k Water Stations 10k Water & Gatorade Station Start/ Finish Porta-potties Keep in Mind: 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!
Hotels Near This Race
Find accommodation close to the start line in Chesapeake, VA. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
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Race Travel Insurance
Don't forget travel insurance for January 16.
You've trained for months and booked a trip to Chesapeake, VA.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
When is Cookie Classic Run 2027 2027 — Chesapeake, VA?
Cookie Classic Run 2027 2027 — Chesapeake, VA takes place on January 16, 2027. The race is held in Chesapeake, Virginia.
Where is Cookie Classic Run 2027 2027 — Chesapeake, VA held?
Cookie Classic Run 2027 2027 — Chesapeake, VA is held at 1246 Dismal Swamp Canal Trail in Chesapeake, Virginia.
Where can I find hotels near Cookie Classic Run 2027 2027 — Chesapeake, VA?
RaceHotelFinder shows hotels sorted by distance from the race venue in Chesapeake. Use the map or list view on this page to compare options and book race weekend accommodation.
