39th Annual Loudoun Street Mile 2026 — Winchester, VA
The 39th Annual Loudoun Street Mile takes place on Loudoun Street in Winchester, Virginia, on May 25, 2026. The event offers both running and walking options across two distances: a full mile and a 100-yard distance. With a typical start time of 8:00 AM, the race accommodates early risers. Entry fees range from free to $35, making it accessible across different budgets. Whether you're targeting a competitive mile effort or prefer the shorter 100-yard option, this established local race provides a straightforward racing opportunity in downtown Winchester.
Hotels Near This Race
Find accommodation close to the start line in Winchester, VA. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
39th Annual Loudoun Street Mile 2026 — Winchester, VA
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Race Travel Insurance
Don't forget travel insurance for May 25.
You've trained for months and booked a trip to Winchester, 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
- 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.
Frequently Asked Questions
When is 39th Annual Loudoun Street Mile 2026 — Winchester, VA?
39th Annual Loudoun Street Mile 2026 — Winchester, VA takes place on May 25, 2026. The race is held in Winchester, Virginia.
Where is 39th Annual Loudoun Street Mile 2026 — Winchester, VA held?
39th Annual Loudoun Street Mile 2026 — Winchester, VA is held at Starting Line in Winchester, Virginia.
Where can I find hotels near 39th Annual Loudoun Street Mile 2026 — Winchester, VA?
RaceHotelFinder shows hotels sorted by distance from the race venue in Winchester. Use the map or list view on this page to compare options and book race weekend accommodation.