Sugar Loaf 5K 2026 — Chester, NY

Date
October 3, 2026
Location
Chester, NY
Venue
1351 Kings Highway
Start Time
8:30 AM
Entry Fee
$30.00
Events
Sugar Loaf 5K
Includes
T-Shirt
Register NowRegistration Open
Join us for the third annual USATF-certified Sugar Loaf Run! Get ready to experience the beauty and charm of Sugar Loaf like never before! With the stunning Sugar Loaf Mountain as your backdrop, come run this picturesque, hilly course through the unique artisan hamlet of Sugar Loaf. This event promises not just a run, but an unforgettable journey through one of the most scenic and historic areas in Orange County, NY. Event Details: Location: Start and finish at the Sugar Loaf Performing Arts Center Who: Open to all runners and walkers When: October 3, 2026, 8:30 AM start We invite everyone to be a part of this beautiful fall event, whether you’re a seasoned runner or a casual walker. Join us in celebrating the spirit of community, health, and the natural beauty of Sugar Loaf. Don’t miss out on this unique opportunity to run in a place where every view is a postcard! Be sure to check out our website: https://www.sugarloafcommunityfoundation.com/about-4 for a drive-through race experienc

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Sugar Loaf 5K 2026 — Chester, NY

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Race Travel Insurance

Don't forget travel insurance for October 3.

You've trained for months and booked a trip to Chester, NY. 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
Get a Quote — Faye Travel Insurance

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Frequently Asked Questions

When is Sugar Loaf 5K 2026 — Chester, NY?

Sugar Loaf 5K 2026 — Chester, NY takes place on October 3, 2026. The race is held in Chester, New York.

Where is Sugar Loaf 5K 2026 — Chester, NY held?

Sugar Loaf 5K 2026 — Chester, NY is held at 1351 Kings Highway in Chester, New York.

Where can I find hotels near Sugar Loaf 5K 2026 — Chester, NY?

RaceHotelFinder shows hotels sorted by distance from the race venue in Chester. Use the map or list view on this page to compare options and book race weekend accommodation.