When does the holiday season in Castle Pines start? The tree lights up on the evening of Dec. 4. Most of the season gets booked three weeks earlier, at 8 a.m. on Friday, Nov. 13, when the City of Castle Pines opens tickets and registration for its Winter Wonderland series at The Ridge Golf Course, 1414 Castle Pines Parkway.
The 2026 series has seven listed events over two December weekends. One of them, the Tree Lighting, needs nothing from you except showing up. Every other event comes with a ticket, a registration step or details still to come. If your household in The Canyons wants gingerbread on a Sunday or a carriage ride on a Saturday night, the deciding moment is a weekday morning in mid-November.
| Event | Date and time | What it takes | Price posted by the City |
|---|---|---|---|
| Tree Lighting | Fri., Dec. 4, 5 to 7 p.m. | Free, just show up | Free; VIP is $65 adult, $35 child |
| Holiday Movie Night | Sat., Dec. 5, 5 to 7 p.m. | Ticket | $5 per person |
| Gingerbread House Decorating | Sun., Dec. 6, sessions at 10 a.m., noon, 2 p.m. | Ticket | $20 per person |
| Holiday Bingo | Sat., Dec. 12, sessions at 3, 5, 7 p.m. | Free registration | Free |
| Holiday Carriage Rides | Sat., Dec. 12 and Sun., Dec. 13, 4 to 8 p.m. | Ticket for ages 2 and up | Not yet posted |
| Holly Jolly Brunch | Sun., Dec. 13, 9 a.m. to 3 p.m. | Details coming | Not yet posted |
The one event you can just show up to
The Tree Lighting Celebration opens the series on Friday, Dec. 4, from 5 to 7 p.m. The City lists Santa and his reindeer, a train ride, carolers, hot cocoa, a decorated path and local performers doing seasonal music and dance. The tree is scheduled to light at about 6:45 p.m., with a drone light show afterward if weather and conditions allow. Dogs are not permitted because space is limited.
The free event is the one most people picture when they think of Winter Wonderland. It also doesn't depend on Nov. 13 at all. A family that only wants the lights, Santa and the drones can skip the ticket morning entirely.
The VIP upgrade does depend on it. The City lists VIP tickets at $65 for adults and $35 for children, on sale Nov. 13 at 8 a.m., non-refundable because capacity is limited. The Castle Pines Chamber's Winter Wonderland page describes what that buys: a reserved parking space at The Ridge, plus access to the clubhouse during the evening with a light buffet dinner, desserts, a hot chocolate bar and holiday drinks. For a Canyons household driving over on a December evening, the reserved parking space may matter as much as the buffet. The City pages list no general parking plan.
Last year's VIP passes did sell out. The City's page for the Dec. 5, 2025 Tree Lighting carried the line "VIP Passes are sold out."
The first weekend runs three days in a row
Dec. 4 through 6 is a Friday, Saturday and Sunday back to back at the same address, and the second and third days are both ticketed.
Holiday Movie Night on Saturday, Dec. 5 is The Grinch, from 5 to 7 p.m., at $5 per person. The Chamber's version of the series describes it as a pajama-friendly movie night. At $5 a head, the price is low. Seats are the limit: the City says capacity is limited and tickets are non-refundable.
Gingerbread House Decorating on Sunday, Dec. 6 runs in three sessions, at 10 a.m., noon and 2 p.m., at $20 per person. Because there are fixed session times, the ticket on Nov. 13 is really a choice of time slot. If you have a nap schedule or a Sunday practice to work around, pick your session before 8 a.m.
The second weekend packs four events into two days
Dec. 12 and 13 is the busiest stretch of the series, and every event on it is scheduled at The Ridge.
- Saturday, Dec. 12: Holiday Bingo runs from 3 to 9 p.m., with sessions at 3, 5 and 7 p.m. It is free, but advance registration is required, and registration opens Nov. 13 at 8 a.m. Holiday Carriage Rides run the same evening from 4 to 8 p.m., with rides through Castle Pines.
- Sunday, Dec. 13: Carriage Rides run again from 4 to 8 p.m. The Holly Jolly Brunch is listed from 9 a.m. to 3 p.m., and the City says more details are coming.
Bingo is free, so it's easy to forget it needs a registration. Free events that require advance sign-up tend to catch families off guard, because no payment screen reminds anyone to book.
Carriage ride tickets are required for everyone age 2 and older, and like the other paid events they are non-refundable. The 2026 pages don't list a ticket price yet. Bingo and the carriage rides overlap on Saturday evening, so a family that wants both on Dec. 12 can line up a bingo session and a ride time instead of guessing on the night.
For the brunch, the most recent posted prices are from 2025: $65 for adults 13 and older, $39 for children 2 to 12, and free for infants under 2, with seatings at 9 a.m., 11 a.m. and 1 p.m. Those numbers give a rough sense of scale, but they are last year's. The Chamber describes the 2026 brunch as a family meal with Santa and a reading of The Night Before Christmas. The Chamber listing shows the time as "9:00PM - 3:00PM." The City lists 9 a.m. to 3 p.m., and the City page is the one to plan around.
What Nov. 13 looks like in practice
The Castle Pines Chamber puts it plainly: "Most events require pre-registration, so don't wait to sign up—these cherished holiday experiences sell out every year!" The City gave a similar warning in 2024, when reservations opened on Friday, Nov. 8 and its 2024 Winter Wonderland preview told residents, "Spots will fill up fast, so reserve your ticket early!" The Friday-in-early-November opening has become the pattern.
For a Canyons household, the morning breaks into a short sequence:
- Decide the weekends before 8 a.m. Dec. 4 to 6 is lights, a movie and gingerbread. Dec. 12 and 13 is bingo, carriage rides and brunch. Few families will do all seven.
- Book timed events first. Gingerbread sessions, bingo sessions and carriage ride times are the choices most likely to narrow as the morning goes on.
- Count every child age 2 and up for carriage rides. The ticket requirement starts at age 2.
- Treat every purchase as final. The City lists the VIP passes, movie tickets, gingerbread sessions and carriage rides as non-refundable.
- Check back for the brunch. Its 2026 details weren't posted alongside the other events.
The drive to The Ridge in December
Every event on the Winter Wonderland calendar uses the same address, 1414 Castle Pines Parkway, so Canyons households make the same drive to all of them. That's why two road projects are worth tracking.
The City's 2026 Castle Pines Parkway Reconstruction has been running since June 1. As of the City's Oct. 5 update, final paving of the remaining eastbound lanes, from Forest Park Drive to near the Buffalo Trail roundabout, was expected in early to mid-November. The City expects the project to finish in fall 2026, and it notes that all timing depends on weather. If that schedule holds, the paving crews should be gone before the Tree Lighting. A cold, wet November could push that back.
The second project is longer. The City lists a late 2026 or early 2027 start for reconstruction of the Happy Canyon Interchange, with completion in mid-2028. It warns of shifted and narrowed I-25 lanes, intermittent ramp closures and nighttime I-25 closures. The planned Canyonside Boulevard connection is set to open after the interchange improvements. None of that is scheduled around Winter Wonderland. Before heading out on a December evening, check that page alongside your tickets.
The rest of the month, closer to home
Winter Wonderland is a two-weekend event, but the Chamber describes one piece as month-long and spread across town: the Reindeer Games Scavenger Hunt, a search across Castle Pines for Santa's nine hidden reindeer. The 2026 dates haven't been posted. Last year's version ran Dec. 11 to 31 through the Eventzee app with the code CPHOLIDAY, and a completed badge could be redeemed for hot chocolate at The Exchange Coffee House. If 2026 follows the same pattern, it fills the weekday gaps between the two big weekends.
A few November dates come before ticket morning:
- Thursday, Nov. 5, 7:30 to 8:30 a.m.: Coffee Klatch with Mayor Tracy Engerman at Ziggi's Coffee, 7298 Lagae Road.
- Saturday, Nov. 7, 9 a.m. to 2 p.m.: Leaf and Pumpkin Composting at Elk Ridge Park, 7005 Mira Vista Lane, free for Castle Pines residents. A practical stop for the jack-o'-lanterns still on the porch.
- Tuesday, Nov. 10, 7 to 9 a.m.: A Comprehensive Plan Pop-Up at The Exchange Coffee House, 1415 Westbridge Drive, where residents can give input on the City's long-range plan.
On the evenings in between, Canyon House is still the neighborhood's own gathering place, and Kitchen & Cocktails runs a seasonal menu. After a December night at The Ridge, it makes an easy last stop on the way home.
The full list of event pages is on the City of Castle Pines events calendar, and tickets open there at 8 a.m. on Friday, Nov. 13.
Once the December tickets are booked, if a move is somewhere on your family's calendar for next year, Inleit Properties would be glad to help you plan the timing well in advance. Start your home story and request a personal consultation.
