Break out the costumes, pumpkins, and favorite chili recipes for the annual Castle Pines Fall Festival! This resident-favorite event returns to the Village Square Shopping Area on Saturday, Oct. 24, from 10 a.m. to 2 p.m.
This free, family-friendly fall tradition will once again bring a variety of seasonal fun, including Trick-or-Treat Street, a farmers market, petting zoo, and the annual Castle Pines Pumpkin Race.
New this year - Inaugural Chili Cookoff!
Think your chili has what it takes? Bring your best recipe and compete for the title of Castle Pines' First Annual Chili Cookoff Champion!
- Register and pay the entry fee of $20 per participant
- Register by October 22 at 5 p.m. to participate! (Click on "Programs" and "2026 Chili Cookoff")
- Prepare approximately 2 gallons of chili (two full crockpots)
- Chili may be red, green, or white
- Give your chili a creative name, which will be displayed at your tasting station
- Have your chili hot and ready to serve by 10 a.m.
- Find the official rules HERE
Not ready to put your recipe to the test? Come hungry and enjoy the festivities before sticking around for another Castle Pines fall favorite.
Pumpkin Race
The annual Pumpkin Race begins at 1 p.m., when creatively engineered pumpkin race cars will take to the course to see which one can roll its way to victory.
- Register to participate WITHOUT purchasing a race kit from the City
- Register to participate AND PURCHASE a race kit for $25 from the City (Click on "Programs" and "Annual Pumpkin Race 2026.")
- Kits must be purchased by Thursday, October 22 at 5 p.m. and must be picked up from the City offices at 7437 Village Square Drive, Suite #200 by Friday, October 23 at noon. (Office is closed for lunch from 12-1 p.m. each day.)
Whether you’re competing, trick-or-treating, or simply looking for a fun way to celebrate the season, make plans to spend your Saturday at the Fall Festival.
Event Details
- FREE to attend
- All Ages
- Date: Sunday, October 24
- Time: 10am - 2pm
- Location: Village Square shopping area, 7437 Village Square Drive, Castle Pines
- Trick-or-Treat Street
- Pumpkin race at 1pm
- Farmer's market
- Petting zoo
- Chili cookoff - NEW for 2026
It's a day jam-packed with fun free activities for the whole family to celebrate the fall season!
About The City of Castle Pines
Castle Pines is a thriving community just south of Denver in Douglas County. Incorporated in 2008, the City is home to approximately 16,000 residents and is growing every year.
We’re business and family-friendly and have access to amazing Colorado recreation opportunities, excellent schools, and world-class new development opportunities.
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