St. James 5 Mile Challenge and 5K Fun Run/Walk – Saint James, NY 2026

Date
May 9, 2026
Location
Saint James, NY
Venue
St. James/Head of the Harbor (Packet pick up at Deepwells Farm)
Start Time
9:00 AM
Events
5 Mile Run (Certified, Timed Event), 5k Fun Run (Untimed), Vendor Village/Community Celebration. Everyone is welcome!
Includes
T-Shirt
Register NowRegistration Open

Registration for the St. James 5 Mile Challenge and 5K Fun Run/Walk costs $35. The event takes place on May 9, 2026, in Saint James, New York, with races at both 5 miles and 5K distances. The race starts at 9:00 AM, with packet pickup held at Deepwells Farm. This event accommodates runners across different distances and fitness levels, making it accessible whether you're targeting a longer 5-mile effort or prefer the shorter 5K distance. Saint James is located on Long Island's North Shore, providing convenient access for regional athletes.

From the Race Organizer
The St James 5 mile challenge is a doozie! The new course starts with an uphill climb leveling off at the half mile mark. From here you have 3 miles of rolling hills through the scenic village of Head of the Harbor before you face the iconic Cordwood Path, which is 1/2 mile incline that would be classified as steep. At the top of the hill you are rewarded with a flat and fast finish. Whether it is a challenging run or a fun walk (shorter route!), every step brings us closer to families in Suffolk County! Support Ronald McDonald House Charities New York Metro (RMHC NYM)! By registering today, you will be supporting RMHC NYM’s Capital Campaign to build a new $34M Ronald McDonald House at Stony Brook Children’s . This new House will keep families seeking medical treatment for their sick children near the care they need and the families they love. 90% of top children’s hospitals around the world are home to at least one RMHC core program. Each Ronald McDonald House is built and sustained w

Hotels Near This Race

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

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St. James 5 Mile Challenge and 5K Fun Run/Walk – Saint James, NY 2026

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Race Travel Insurance

Don't forget travel insurance for May 9.

You've trained for months and booked a trip to Saint James, 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 St. James 5 Mile Challenge and 5K Fun Run/Walk – Saint James, NY 2026?

St. James 5 Mile Challenge and 5K Fun Run/Walk – Saint James, NY 2026 takes place on May 9, 2026. The race is held in Saint James, New York.

Where is St. James 5 Mile Challenge and 5K Fun Run/Walk – Saint James, NY 2026 held?

St. James 5 Mile Challenge and 5K Fun Run/Walk – Saint James, NY 2026 is held at St. James/Head of the Harbor (Packet pick up at Deepwells Farm) in Saint James, New York.

Where can I find hotels near St. James 5 Mile Challenge and 5K Fun Run/Walk – Saint James, NY 2026?

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