Castle Pines puts its two biggest fall events at the same address on back-to-back days. Both happen at the Village Square Shopping Area, 7437 Village Square Drive. Friday, Oct. 23 is the ticketed Bonfire, BBQ, and Brews. Saturday, Oct. 24 is the free Fall Festival, Trick-or-Treat Street, and Pumpkin Race. The calendar makes it look like a weekend you can decide on Friday afternoon. The City's event pages say otherwise. Every part of the weekend that needs a ticket, a kit or a registration closes on Thursday or earlier.

The Week Before, in Order

These are the dates that decide what your weekend looks like, all taken from the City of Castle Pines event listings:

1. Wednesday, Oct. 21, 7–9 a.m. The City holds a Comprehensive Plan pop-up at Ziggi's Coffee, 7298 Lagae Road. Residents can talk about growth, transportation, parks, housing and other long-range topics.
2. Thursday, Oct. 22, 5 p.m. Last chance to buy a $25 Pumpkin Race kit, and the registration deadline for the new Chili Cookoff.
3. Friday, Oct. 23, noon. Kits bought from the City must be picked up by this time at the City offices, 7437 Village Square Drive, Suite #200. The office closes for lunch from noon to 1 p.m.
4. Friday, Oct. 23, 6–9 p.m. Bonfire, BBQ, and Brews at Village Square.
5. Saturday, Oct. 24, 10 a.m.–2 p.m. The Fall Festival, with chili ready to serve at 10 a.m. and the Pumpkin Race at 1 p.m.

Kit pickup is easy to miss. If you buy a kit Thursday afternoon, you have until Friday at noon to collect it, and only during office hours.

Friday Night Is Sold in Advance Only

Bonfire, BBQ, and Brews tickets cost $42 for adults 21 and over and $30 for anyone under 21. A ticket covers a BBQ meal, drinks for guests 21 and over, everything needed for s'mores, access to the firepits and live music from Darling Revival. The City says capacity is limited and all ticket sales are final. The Castle Pines Chamber of Commerce adds that tickets must be bought ahead of time and none will be sold at the gate.

Tickets are sold through the City's parks and recreation programs portal. If "Bonfire, BBQ, and Brews" doesn't appear on the first screen, the City says to click "Programs" at the top of the page.

Since dinner comes with the ticket, Friday doesn't need a restaurant plan. A household of two adults and one teenager would pay $114. Because sales are final, settle on the headcount before you check out.

Saturday Is Free, but Two Activities Have Fees and Deadlines

The Fall Festival costs nothing to attend. It includes Trick-or-Treat Street, a farmers market, a petting zoo, the annual Castle Pines Pumpkin Race and, for the first time, a Chili Cookoff. The two activities that put you in the competition are the ones with the Thursday deadline.

The Pumpkin Race starts at 1 p.m. Racers bring a pumpkin already built into a race car. You can register without buying anything, or pay $25 for a City kit. Kits must be purchased by Oct. 22 at 5 p.m. The City publishes rules and regulations that decide whether a pumpkin is eligible, so check them before you start building.

The Chili Cookoff charges $20 per participant. The requirements are specific:

• About 2 gallons of chili, or two full crockpots
• Red, green or white chili are all allowed
• A creative name, which will be displayed at your tasting station
• Chili hot and ready to serve by 10 a.m.

Registration also closes Oct. 22 at 5 p.m., and the official rules are posted on the City's site. The 10 a.m. serving time matches the festival's opening. Anyone cooking will be setting up while the first families arrive for Trick-or-Treat Street.

The Two-Hour Gap Before Dinner on Village Square Lane

The festival ends at 2 p.m. The newest restaurant on the block opens at 4. Castello Italiano, at 361 Village Square Lane, Suite 130, soft-opened Aug. 31 and officially opened Sept. 1 in the space Pino's used to fill. DougCo Social reports that co-owners Petrit and Erion come from the family behind Farro Italian Restaurant.

At opening, Castello was dinner-only. It was listed at 4–9 p.m. Tuesday through Saturday and 4–8 p.m. Sunday, closed Mondays. Walk-ins are welcome, but reservations are recommended. The opening menu included baked brie with prosciutto and fig, white bolognese, bison short rib ravioli, wild boar ragu, lamb shank, cioppino and a 16-ounce ribeye. DougCo Social's first-person review singled out the bison ravioli and the Italian lemon cake. Because Saturday dinner falls on the same day as a free, family-wide event one block over, it makes sense to book Castello when you buy bonfire tickets, not after the pumpkin race. Hours set at opening can change, so confirm them before you go.

Castello isn't the only option on the lane. Duke's Steakhouse lists its Castle Pines location at 363 Village Square Lane. Pho 5 shares that address and offers dine-in, takeout and delivery. Tandoori Flames Indian Scratch Kitchen, at 556 Village Square Lane, Suite 200, serves North Indian dishes at dinner. Before the festival, Alta Empanada at 363 Village Square Lane, #145 serves empanadas, pastries, desserts and specialty coffees. That puts a sit-down dinner, takeout pho and a morning pastry within one short walk of the festival grounds.

Getting There While Castle Pines Parkway Is Still Being Paved

The weekend falls during the last stretch of the 2026 Castle Pines Parkway reconstruction. Work started June 1. The westbound section from Monarch Boulevard to Deer Clover Drive, including the stretch in front of Timber Trail Elementary, reopened Aug. 11. The City's Oct. 1 update lays out what's left in order:

The job grew in July. On July 14, City Council approved replacing the concrete between Forest Park Drive and the Buffalo Trail roundabout with asphalt after crews found more damage than expected. Within the construction zone, traffic in both directions has been sharing the eastbound lanes. The City still targets completion for fall 2026. Even so, two paving phases still have to follow a testing step that begins the week of Oct. 5. If you live west of Deer Clover, plan for lane shifts on the evening of Oct. 23 and check the City's project page that day.

Where the Pumpkins Go After the Race

The season keeps going after Oct. 24. On Saturday, Nov. 7, from 9 a.m. to 2 p.m., the City runs a free Leaf and Pumpkin Composting event for residents at Elk Ridge Park, 7005 Mira Vista Lane. That's two weeks after the race, which is enough time for any pumpkin that survived to retire from the porch.

That same month, Life Time says its Castle Pines club at 7373 Canyon Forge Drive is "Arriving November 2026." The company describes more than 102,000 square feet with indoor and outdoor pickleball, pools, Kids Academy and hydrotherapy suites. That date comes from the company, and a 2025 Castle Pines Connection report said early 2027 was expected, so treat November as slated, not settled. The second Comprehensive Plan pop-up follows on Nov. 10, 7–9 a.m., at The Exchange, 1415 Westbridge Drive.

Coyote Ridge Park will be under construction for the whole season. Phase 1 began Sept. 8, and the City's Oct. 2 update had crews working on the baseball field and the outfield retaining wall. The City estimates the work will finish in spring 2027.

At Dolby Haas, we follow the Castle Pines calendar the way we follow the local market, one deadline at a time. If this fall has you wondering what your home might be worth before the next season starts, request a free home valuation and we'll walk you through the numbers.