The Pumpkin Patch Dash 5K takes place at 1055 Pawley Way in Winter Garden, Florida on October 17, 2026. The event offers two running distances: a 5K and an 880-yard option, making it accessible for runners of different abilities and ages. The race starts at 5:50 PM, so plan your travel and pre-race routine accordingly for an evening event. Entry fees range from free to $45, depending on registration options. Winter Garden provides a convenient central Florida location for athletes traveling to compete. Whether you're running the full 5K or the shorter 880-yard distance, this fall-themed race offers flexibility for your racing schedule.
From the Race Organizer
The West Orange Junior Service League is excited to host this year’s 17th Annual 5K as the 'Pumpkin Patch Dash' on Saturday, October 17, 2026. All proceeds from the race will go towards the West Orange Junior Service League Scholarship Fund! Your contributions and support will directly impact local high school seniors in our community to achieve their college goals. Come run or walk this evening race and enjoy the creative decorations through beautiful Oakland Park in Winter Garden. This unique, nighttime, family-friendly 5K is sure to be fun for everyone. Bring your friends, family, or a team to create new healthy, autumnal traditions and memories. This event features a 5K, a Kid’s Fun Run, games, treats, festive activities, food trucks, live DJ, and much more. Each registered 5K participant will receive a timed race, dry-fit t-shirt, goodie bag, finisher’s medal, and post-race snacks. We will have prizes for our top finishers (best time) and a special cash prize for our top under 18 years old runners in the main race. We have two options for kids prior to the official 5K. Ages 6-11 are invited to participate in the 1/2 mile kids' run. Kids 5 and under will have a shorter fun race up the street for free. All kids MUST register and sign a waiver online prior to the event. If you would like a race shirt for your child, they will be available for an additional fee. Registration for this event will close at 5:30 pm on race day. PARKING AT THE RACE: PLEASE REFERENCE THE MAP BELOW There will be signs directing you to parking for the race. THERE IS NO PARKING AT THE ACTUAL SITE!! There will be shuttle buses running from the parking site to the race site every 10-15 minutes starting at 4:45 pm. Packet pick-up - TBD Race site pickup will be held Saturday, October 17 from 4:45 - 5:45 p.m. at Oakland Park race site (KIDS RACE MUST REGISTER BY 5:30PM) Young Kids' Fun Run starts at 5:50 PM (Ages 5 and under); Older Kids' 1/2 Mile Run starts at 6:00 PM (Ages 6-11) 5K Run/Walk starts at 6:30 PM - the start line will be left open for 5 minutes. Results are based on chip times. The course will have a water stop around midway. This year celebrates our 17th anniversary of our 5K in Oakland Park. We want to thank everyone who has participated over the years to make this such a successful fundraising event. We would like to extend an extra special THANK YOU to the residents of Oakland Park for allowing us to host this event in their beautiful community. All the money raised from this 5K will go directly toward the WOJSL's Scholarship Fund, serving local community high school seniors. The West Orange Junior Service League is a nonprofit organization comprised of a dedicated and compassionate group of women who come together to benefit our community by philanthropic stewardship. Each year, the WOJSL has three fundraising events: a 5K, Winter Garden Christmas Golf Cart Parade, and the ever-so-popular Run for the Roses Derby Event. Monies raised at these events are then dispersed annually to local nonprofit organizations through our grant process or directly to students through the Scholarship Fund. Please email WOJSL5K@gmail.com if you are interested in securing a sponsorship today. Sponsorships are due on or before September 18! Whether this is your first year or 17th year, we welcome you to join us with your family, friends, co-workers, running buddies!
Hotels Near This Race
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Race Travel Insurance
Don't forget travel insurance for October 17.
You've trained for months and booked a trip to Winter Garden, FL.
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 Pumpkin Patch Dash 5K 2026 — Winter Garden, FL?
Pumpkin Patch Dash 5K 2026 — Winter Garden, FL takes place on October 17, 2026. The race is held in Winter Garden, Florida.
Where is Pumpkin Patch Dash 5K 2026 — Winter Garden, FL held?
Pumpkin Patch Dash 5K 2026 — Winter Garden, FL is held at 1055 Pawley Way in Winter Garden, Florida.
Where can I find hotels near Pumpkin Patch Dash 5K 2026 — Winter Garden, FL?
RaceHotelFinder shows hotels sorted by distance from the race venue in Winter Garden. Use the map or list view on this page to compare options and book race weekend accommodation.
