Where did Crestline's Christmas tree get lit last year? It was lit on Monday, Dec. 1, 2025, during Goodwin's Family Christmas Bonfire in Lake Gregory's North Shore parking lot. By then the decorations had been up for days. The Alpine Mountaineer reported that the countdown was yelled across the lake, County Fire firefighters built the bonfire, and Santa arrived on a fire engine.
This year the lighting comes first. Holidays in the Pines runs from Nov. 28 through Jan. 3 under a new storybook theme, "Once Upon A Toyland." It opens with a town-and-tree lighting at Lake Gregory and reaches its peak with something the lake has never hosted. Last year the season ran along Lake Drive's storefronts and dipped down to the water once. This year Lake Gregory holds both the start and the peak, and the shop and street events happen on the weekends in between.
The Lighting Now Opens the Season
The Holidays in the Pines Town & Tree Lighting is set for Saturday, Nov. 28, from 5:30 to 6 p.m. at Lake Gregory Recreational Park, 24171 Lake Drive. The listing calls it the moment that "officially" starts the season. The Crestline Chamber of Commerce's own listing puts the event on the same date at Lake Drive and Crest Forest Drive.
Last year the season started up the hill on Nov. 29, 2025, with Breakfast with Santa at Mountain Cravings in Top Town, and the tree came on two days later. The 2026 schedule puts the lake first. On opening Saturday the day runs downhill. Carolers fill Downtown and Top Town Crestline from noon to 4 p.m., and the lighting at the lake follows about 90 minutes later.
At the joint Crest Forest and Lake Arrowhead Municipal Advisory Council meeting at San Moritz Lodge on Oct. 6, Candace Pearson of the Lake Gregory Community Advisory Committee said 60,000 people came through the Lake Gregory gates this summer. The Alpine Mountaineer covered the meeting. This year the holiday calendar is built around the same lake.
Dec. 19 Puts Lights on the Water
The new event this season is the 1st Annual Holidays in the Pines Boat Parade. The Crestline Chamber of Commerce and Lake Gregory Company are presenting it on Saturday, Dec. 19, and they bill it as the start of "a brand-new Crestline holiday tradition." The schedule:
- 2:00 to 4:30 p.m.: Boat decorating and preparation
- 5:00 to 7:00 p.m.: The parade, with boats lined up in the order they arrive
- Registration deadline: Dec. 6, 2026
- Boats: Duffy boats go to local nonprofits first, then to other participants. Personal boats are welcome only if they are human-powered or electric. Oil- and gasoline-powered boats are not allowed.
If you're watching from shore, it's free. Viewing is at the Lake Gregory North Shore Terrace, with food vendors and hot drinks, wine and cider for sale. That's the same north shore where last year's bonfire and lighting happened, so the waterfront's holiday night now features lit boats on the lake instead of a fire in the parking lot.
The Dec. 6 deadline matters if you belong to a church group, a Scout troop or a service club. Nonprofits get the first claim on Duffy boats, but that priority only helps groups that register in time. The Alpine Mountaineer's report on the MAC meeting also noted that local nonprofits and other groups can apply to reserve a boat as part of the Holidays in the Pines celebrations.
The Weekend Everything Lands On
Dec. 19 is the last Saturday before Christmas, so it's more than parade night. Four of the season's events overlap that weekend:
| What | When | Where |
|---|---|---|
| Caroling | Dec. 19 and 20, noon to 4 p.m. | Downtown and Top Town Crestline |
| Santa and Mrs. Claus | Saturday afternoon, Dec. 19 | In town, per the Saturday schedule |
| Boat Parade | Dec. 19, 5 to 7 p.m. | Lake Gregory, viewing from North Shore Terrace |
| Tree contest voting closes | Dec. 20 at midnight PST | Online at Visit Crestline |
Saturday, Dec. 19, follows the same pattern as opening night. The street events run uphill in the afternoon, and the evening ends at the lake. Carolers finish at 4 p.m., parade boats are already being decorated by then, and the parade starts an hour later. You can cover both on foot or with a short drive. The tree contest closes the next night, so that weekend is your last chance to vote.
The Weekends in Between
Between opening night and parade night, the season moves away from the water and into town. Each part comes with its own dates.
Holiday Bingo starts Friday, Nov. 27, the day before the lighting. Collect stamps at participating businesses, then turn in your completed card for a raffle. The program page says "Holiday Bingo is BACK!", so the game returns from last year. In 2025, shoppers picked up cards at chamber member merchants and earned a sticker with each local purchase.
The tree contest has eight categories this year, including one for the "Once Upon A Toyland" theme. Voting opens Nov. 27 and closes Dec. 20 at midnight PST.
Caroling runs every weekend of the season from Nov. 28–29 through Dec. 19–20, noon to 4 p.m., in Downtown and Top Town.
Santa and Mrs. Claus visit town every Saturday afternoon during the season, according to Visit Crestline's program page, which adds "if the Grinch doesn't beat you there!" The same page invites visitors to sip hot cocoa or cider from local shops.
The rest of December's calendar fills the midweeks and the weekends between:
- Dec. 4–5: The Camp Holiday Market at the Twin Peaks Farmers Market has shopping, a mimosa bar, food trucks, treats and live music. It's in neighboring Twin Peaks, outside Crestline proper.
- Dec. 6: Boat parade registration closes.
- Dec. 12: The Mountain Fifes and Drums Colonial Christmas Concert is at San Moritz Lodge.
- Dec. 15: The Mountainpreneurs networking meetup and the Chamber's open board meeting are on the Crestline Chamber calendar.
- Every Tuesday and Thursday: Senior nutrition lunches continue at San Moritz Lodge through December, and the VFW Chess Club meets on Thursdays.
Before the Lights Go On
The holiday season really starts two days before the lighting. The Crestline-Lake Gregory Rotary Club is hosting a free community Thanksgiving dinner on Thanksgiving Day, Nov. 26, with doors opening at noon. The Alpine Mountaineer reported that the Rotary is asking for help with food prep and volunteer shifts on Wednesday, Nov. 25. The Rotary's site lists the Community Thanksgiving Dinner as one of the causes you can donate to.
That leads straight into the opening weekend:
- Thursday, Nov. 26: Rotary community Thanksgiving dinner, doors at noon
- Friday, Nov. 27: Bingo cards and tree contest voting open
- Saturday, Nov. 28: Caroling from noon to 4 p.m. uphill, then the tree lighting at Lake Gregory Recreational Park at 5:30 p.m.
- Sunday, Nov. 29: Caroling again from noon to 4 p.m.
The season ends on Jan. 3, 15 days after the parade. Last year The Alpine Mountaineer described the decorations as staying up into the New Year, through the twelfth day of Christmas. Expect the lights at the lake and along the streets to stay on into early January.
If your Crestline cabin will host family on Dec. 19, or sits empty while you're down the hill for the holidays, SoCal Resorts can help with seven-day local support, guest-ready prep and an honest read on what the place is worth this season. Get a free home valuation, and we'll see you at the lake.
