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

The Sugar Loaf 5K takes place on October 3, 2026, in Chester, New York, at 1351 Kings Highway. This 5K running event starts at 8:30 AM and offers a straightforward race option for runners looking for a standard distance competition. The entry fee is $30.00. Whether you're training through fall race season or targeting a specific goal time, this local event provides a no-frills option in the Hudson Valley region. Book accommodation in Chester to minimize travel time on race morning and allow time to scout the venue and parking situation before your 8:30 AM gun time.

From the Race Organizer
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.org/about-4 for a drive-through race experience, course map, and ideas for things to do while visiting Sugar Loaf. There is so much to do and see! Register early for a race T-shirt.

Hotels Near This Race

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

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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

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

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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.