Sugar Loaf 5K
Sugar Loaf 5K is a running race on October 3, 2026 in Chester, NY, with an entry fee of $30.
- Date
- October 3, 2026 (72 days to go)
- Location
- 1351 Kings Highway, Chester, NY
- Price
- $30
- Sport
- Running
From the 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.
Events
Weather
Typical Conditions
It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.
Typical High
67°
Typical Low
47°
Chance of Rain
27%
Based on US Climate Normals data from Middletown 2 Nw, 13 mi from the venue.
Host City
About Chester, NY
Population
4,052
as of 2023
City Elevation
455 ft
Nearest Airport
SWF
New York Stewart International Airport · 13 mi
Major Hub
LGA
LaGuardia Airport · 45 mi
Time Zone
Eastern Time
From Endurance Grid
A small town race. Lodging near the start could be limited, so book early.
Race Location
Your Next Start Line
What Are You
Waiting For?
Every finish line starts with a single decision. Claim your spot at Sugar Loaf 5K, put it on the calendar, and turn “someday” into a start date.
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From Endurance Grid
About This Sport
Endurance Grid is here to help you understand the sport, decide if it’s the right fit, and learn how to prepare. For course distances, logistics, and race-day specifics, always defer to the race organizer’s event page.
With running, there's a distance for every fitness level, a community at every start line, and nothing beats the feeling of crossing a finish line you trained for.
Running is an endurance sport that rewards consistency, and showing up every week compounds in ways that will surprise you.
Running
From 5K to marathon, running races are an accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Coming Up
More Running races near Chester, NY
The Third Annual Orange Runners Club Summer Sizzle XC5k
5K · From $31 · 144 Sanfordville Rd
7 miles away
Trot For Trauma
5K · From $35 · 94 Grove Street
11 miles away
Warwick Lions Club Annual Labor Day 5K & 5 MIle Road Race and Kids Fun Run
5K · 8K / 5 Mile · From $35 · 225 West Street Warwick Middle School
7 miles away
Orange Peel to Pavement
5K · From $5 · Thomas Bull Memorial Park
9 miles away
Plan your trip
Make it a Racecation
Coming from out of town? There's more to Chester than race day. We'll help you line up nearby lodging, flights, a rental car, and things to do so you can make the most of your racecation.
Plan your trip to ChesterFrequently Asked Questions (FAQs)
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Sugar Loaf 5K
Oct 3, 2026