The Bear Crawl 2026 — Williamsburg, KY

Date
September 12, 2026
Location
Williamsburg, KY
Venue
81 Rant St
Start Time
8:00 AM
Entry Fee
$20.00
Events
The Bear Crawl
Includes
T-Shirt
Register NowRegistration Open
🏃‍♂️🐻 Ready to crush The Bear Crawl? We’re a small school with a big heart, and this is our biggest fundraiser of the year! Race through downtown, right in the middle of the Old Fashioned Trading Days festival — food, fun, and old-school vibes everywhere you go. A few miles. A few hours. A lifetime of memories. Lace up, show up, and run for a cause! 🏅✨

Hotels Near This Race

Find accommodation close to the start line in Williamsburg, KY. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.

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The Bear Crawl 2026 — Williamsburg, KY

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Race Travel Insurance

Don't forget travel insurance for September 12.

You've trained for months and booked a trip to Williamsburg, KY. 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
  • Emergency medical up to $250,000
  • Cancel For Any Reason add-on available
  • 24/7 real-time support

Affiliate links — we may earn a commission at no cost to you. Coverage terms vary by state and plan. Review policy details before purchase.