The 33rd Annual Weston Memorial Day Weekend 5K & Kids Fun Run is a running event featuring a 1 mile and 5K distance, taking place on May 29, 2027, at Weston High School in Weston, Connecticut. Entry fees range from $15.00 to $45.00, with a typical start time of 7:45 AM.
From the Race Organizer
5K COURSE USATF-certified 5K course features a scenic, tree-lined course through the heart of Weston. Run, jog, or walk the 5K (3.1 miles) course. Start & finish at Weston High School. THE KIDS ZONE & FUN RUNS Kids Fun Runs include 3 distances with ribbons for all the racers! Lightening Dash (100 yards) One Lap Loop (1/4-mile) The Mighty Mile (1-mile) Located on the Weston High School track at the football stadium Kids Fun Zone includes a giant inflatable obstacle course, Face Painting, Temporary Tattoos, and a water station. RACE PACKET PICK-UP Location: Weston High School Cafeteria 115 School Road, Weston, CT 06883. Please enter through the doors by the flagpole; follow signs to the WHS cafeteria. Packet Pickup Hours: Thursday, May 21: 3pm - 6pm Friday, May 22: 3pm - 6pm Saturday, May 23 (Race Day): 7:00am - 8:15am Note: Packets and/or Race Shirts not picked up by 8:15am on Saturday, May 23, 2026, will be reallocated to inventory for use with a potential participant. The event is rain or shine unless weather is deemed unsafe as determined by town officials. There are no refunds. RACE DAY INFORMATION Kids Fun Run & Kids Zone Located at the WHS Football field; the Kids Fun Run will take place on the WHS Track. 7:45am: Kids Fun Run races (100 yd, ¼ mile, 1 mile) will start promptly at 7:45am. Please plan to be on the track by 7:40am to begin lining up. Parents are welcome to run alongside their child, if desired. Participants will be awarded ribbons, with the speedsters earning Fun Run medals. The Fan Favorite, oversized Inflatable Obstacle Course awaits with Face Painting, Temporary Tattoos, and a water station in the Kids Zone. WHS Student Government will be hosting a bake sale inside the school and at the Kids Fun Zone to help fund student activities, for those who’d like to support their efforts 🍪 5K Run/Walk 8:30am: 5K Run/Walk will begin at 8:30am with a NEW 3-Wave start, based on your estimated 5K time. Please determine your Wave from the image below; there will be approx. 90 seconds between Waves. Your personal race time (chip/net time) starts when you cross the Start Line and ends as you cross the Finish Line. Timing is done through a ChronoTrack B-tag attached to your race bib. Please don’t fold or bend and wear it facing FRONT for accurate timing. Water stations for 5K participants located just beyond the ½ way mark on-course and at the Finish Line. Based on runner feedback, we’re excited to offer our 5K finishers an expanded variety of complimentary fruits and snacks just beyond the Finish Line! Parking & Traffic Flow Free parking is available in any of the parking lots at the schools. Please do NOT park along School Road (including any marked for parking) to ensure course flow and safety. The 5K course is open to local traffic; please stay in the RIGHT lane only. Weston’s finest (WPD) and Road Safety personnel will be along the course to assist. AWARDS 5K Awards Top 3 overall, male/female 5K Age Group Medals: 8 & under, 9-10, 11-12, 13-14, 15-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70+ Awards will follow standard road race practices, with overall winners determined by gun time and age-group awards based on chip time. Consistent with most races, we do not ‘double award’ the overall winners; overall award winners will be excluded from age-group award categories, allowing recognition of more participants. Kids Fun Run Awards: Ribbons for all our youngest racers! COURSE MAP
Course & Travel Notes
Sunrise on race day is at 5:24 AM, with the 33rd Annual Weston Memorial Day Weekend 5K & Kids Fun Run starting at 7:45 AM. The venue sits at 351 ft elevation. May weather normals for the race location include an average high of 72°F and average low of 50°F, with measurable precipitation occurring on 40% of days. Westchester County Airport (HPN) is 19.8 miles from the venue.
⛰️ 351 ft elevation☀️ Typically 72°F / 50°F · 40% chance of rain✈️ Westchester County Airport (HPN) — 19.8 mi
Hotels Near This Race
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33rd Annual | Weston Memorial Day Weekend 5K & Kids Fun Run 2027 — Weston, CT
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Race Travel Insurance
Don't forget travel insurance for May 29.
You've trained for months and booked a trip to Weston, CT.
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
When is 33rd Annual | Weston Memorial Day Weekend 5K & Kids Fun Run 2027 — Weston, CT?
33rd Annual | Weston Memorial Day Weekend 5K & Kids Fun Run 2027 — Weston, CT takes place on May 29, 2027. The race is held in Weston, Connecticut.
Where is 33rd Annual | Weston Memorial Day Weekend 5K & Kids Fun Run 2027 — Weston, CT held?
33rd Annual | Weston Memorial Day Weekend 5K & Kids Fun Run 2027 — Weston, CT is held at Weston High School in Weston, Connecticut.
Where can I find hotels near 33rd Annual | Weston Memorial Day Weekend 5K & Kids Fun Run 2027 — Weston, CT?
RaceHotelFinder shows hotels sorted by distance from the race venue in Weston. Use the map or list view on this page to compare options and book race weekend accommodation.
