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
Hotels Near This Race
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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
