Westlake's holiday season opens in stages over about two and a half weeks. The Promenade at Westlake goes first on Friday, Nov. 20. The Westlake Village Inn follows the day after Thanksgiving. The Four Seasons Hotel Westlake Village starts its nightly snowfall on Dec. 1. Then two volunteer-run events end the first stretch on the same Sunday afternoon. Each of these hosts sets its own terms. Some events are free and happen once. Some repeat every night for a month. Some are ticketed workshops. Two of them run on donations.
Knowing which is which makes planning easier. If you go to only one event, you miss most of the season. If you know the order, you can fit everything from the first lit tree to the last carol into about two and a half weeks without rushing any of it.
Friday, Nov. 20: The Promenade goes first, for one evening
Christmas at The Promenade at Westlake runs from 4 to 8 p.m. on Friday, Nov. 20. The show has music, Santa's arrival and fireworks at the end. The Promenade's event page lists pre-show activities starting at 4 p.m.: strolling performers, kids' activities, in-store offers and a Holiday Market with treats from the center's restaurants and shops. According to Conejo Valley Guide, the performers include carolers and candy cane stilt walkers. The guide also recommends arriving early.
The tree is a 60-foot white fir with 4,000 lights. The Promenade lists it on display from Nov. 15 through Dec. 25. So the tree stays up for six weeks, but the show with Santa and fireworks happens on one night only.
The next morning, the Promenade switches to bookings
The day after the lighting, Santa's Cottage opens at 140 Promenade Way, near Farfalla Trattoria. It runs through Dec. 24. The Promenade's Santa page welcomes walk-ins but says waits vary. The booking page recommends reservations and says walk-ups are served only when slots are open. Photo packages are sold on the reservation page:
| Package | Price | What's included |
|---|---|---|
| Holly Jolly | $50 | Three 5x7 prints |
| Deck the Halls | $65 | Four 5x7 prints, digital album and video |
| Holiday Magic | $85 | Five prints of your choice, digital album, video, and two ornaments or magnets |
Pets get their own evenings. Pet-photo nights are Nov. 25 and Dec. 2, 9 and 16, each from 4 to 7 p.m. The first one is the night before Thanksgiving. That's a good time to get the dog's photo done before family arrives.
Thanksgiving week hands off to the Westlake Village Inn
Thanksgiving itself centers on the two big hospitality venues. The Four Seasons lists Thanksgiving specials at Coin & Candor and a Thanksgiving brunch buffet at The Hamptons on Nov. 26. It also offers a Turkey To-Go meal for four to six people, with pickup starting Nov. 25. The Westlake Village Inn's calendar lists a Mediterraneo Thanksgiving Dinner.
The next afternoon, Friday, Nov. 27, the inn holds its Stonehaus Tree Lighting starting at 4 p.m., according to the Westlake Village Inn calendar. This is the season's second tree lighting, exactly one week after the first. It's also on Black Friday, so it works as a stop after a day out with visiting family.
Dec. 1: The Four Seasons repeats every night
The Four Seasons does something different from the one-night events. Its 2026 festive season announcement says snow will fall on the hotel's front drive every day from Dec. 1, 2026, through Jan. 1, 2027, every half hour from 5 to 8 p.m. That makes it the most flexible event of the season. If one evening doesn't work, the snow falls again 30 minutes later, and again the next night.
The hotel's dining specials follow the same nightly pattern. Starting Dec. 1:
- Alpine Fondue at Prosperous Penny, the hotel's 1920s-inspired bar: Swiss Gruyère fondue for two, Monday through Friday, $55 plus tax and gratuity.
- Après Ski Girl Dinner, also at Prosperous Penny: Saturdays and Sundays from 5 p.m. to close, $65 per person plus tax and gratuity.
- Yakitori Nights at Onyx: American Wagyu skewers and seasonal robatayaki, Wednesday through Saturday from 5 p.m. to close.
The hotel's workshops are open to both guests and locals, according to the release. They're spread through December, and most run on a single date:
- Wreath Making: Wednesday, Dec. 2, and Friday, Dec. 4, at 5 p.m., $95 per person, ages 15 and older
- Floral & Flutes: Friday, Dec. 11, at 6:30 p.m., $80 per person, with a glass of champagne
- Behind the Line steak cooking class: Thursday, Dec. 17, at 5:30 p.m., $195 per person
- Paint & Sip: Friday, Dec. 18, at 5 p.m., $65 per person
- Gingerbread Building & Photos with Santa: Tuesday, Dec. 22, from 1 to 2:30 p.m. or 4 to 5:30 p.m., $55 per person
Workshop reservations go through the hotel's Eventbrite page. If you sign up for the Dec. 4 wreath class, you'll have a handmade wreath on the door before the first weekend of December.
Dec. 5 and 6: Two community events take over
By the first weekend of December, the events shift from commercial venues to volunteer groups. Both weekend events support local nonprofits.
The Rotary Club of Westlake Village hosts the 5th Annual Holidays in the Village, A European Marketplace, at The Oaks. According to Conejo Valley Guide, it's held in the parking lot at W. Wilbur Rd. and W. Thousand Oaks Blvd., and proceeds go to local nonprofits. The event's plan-your-visit page gives the hours: 11 a.m. to 8 p.m. on Saturday, Dec. 5, and noon to 6 p.m. on Sunday, Dec. 6. Admission and parking are free, and no tickets are needed. There are about 60 artisan shops for holiday gifts. Food is in the Festive Garden and Le French Quarter: bratwurst, soft pretzels, French pastries, Glühwein, mimosas, apple cider and hot cocoa. Kris and Mrs. Kringle host the Kris Kringle Village, which has face painting, Art Trek holiday crafts, a holiday train and a Village Bear Scavenger Hunt.
On Sunday, the City of Westlake Village and The Shoppes at Westlake Village hold the annual Holiday Sing-Along from 3 to 6 p.m. in the Fountain Courtyard at The Shoppes, 30770 Russell Ranch Road. There's caroling, live music, food, a photo booth, hot cocoa and face painting. The city's Sing-Along page lists three donation recipients: Manna Conejo, Casa Pacifica and Books R' Us. You get one raffle ticket for each item you donate. The city's Oct. 26 announcement asks attendees to bring donations for local nonprofits.
So the Sunday market hours and the Sing-Along overlap from 3 to 6 p.m. Here's a simple way to do both:
- Get to the European Marketplace when it opens at noon Sunday.
- Do your gift shopping and eat in the Festive Garden or Le French Quarter before mid-afternoon.
- Bring your donations from home: food for Manna Conejo, gifts for Casa Pacifica, books for Books R' Us. More items mean more raffle tickets.
- Head to the Fountain Courtyard at The Shoppes for the caroling and the rest of the Sing-Along.
If you want the market's longer hours, go Saturday instead, when it's open until 8 p.m. That leaves Sunday for the Sing-Along.
The season on one list
- Nov. 15 to Dec. 25: The Promenade's 60-foot white fir on display
- Fri., Nov. 20, 4 to 8 p.m.: Christmas at The Promenade at Westlake, with the Holiday Market from 4 p.m.
- Nov. 21 to Dec. 24: Santa's Cottage, 140 Promenade Way
- Wed., Nov. 25, 4 to 7 p.m.: First Santa's Cottage pet-photo night, plus the Four Seasons Turkey To-Go pickup begins
- Thu., Nov. 26: Thanksgiving at Coin & Candor and The Hamptons
- Fri., Nov. 27, 4 p.m.: Stonehaus Tree Lighting at the Westlake Village Inn
- Dec. 1 to Jan. 1, 5 to 8 p.m.: Snowfall on the Four Seasons front drive every half hour
- Dec. 2, 9 and 16, 4 to 7 p.m.: More Santa's Cottage pet-photo nights
- Wed., Dec. 2, and Fri., Dec. 4, 5 p.m.: Four Seasons wreath making
- Sat., Dec. 5, 11 a.m. to 8 p.m., and Sun., Dec. 6, noon to 6 p.m.: Holidays in the Village at The Oaks
- Sun., Dec. 6, 3 to 6 p.m.: Holiday Sing-Along at The Shoppes at Westlake Village
- Fri., Dec. 11, 6:30 p.m.: Floral & Flutes at the Four Seasons
- Thu., Dec. 17, 5:30 p.m.: Steak cooking class at the Four Seasons
- Fri., Dec. 18, 5 p.m.: Paint & Sip at the Four Seasons
- Tue., Dec. 22: Gingerbread Building & Photos with Santa at the Four Seasons
- Fri., Dec. 25, 11 a.m. to 3:30 p.m.: Christmas Day Brunch Buffet at The Hamptons, $250 for adults and $100 for children under 12, plus tax and gratuity, with Santa from 12:30 to 2 p.m. Reservations are on OpenTable.
If this season has you thinking about how your home handles a full house, a long table or a driveway that could use better lighting, The Jenna Kaye Group can walk the property with you and talk through what's worth doing before next December. Request a private consultation and a tailored plan for your home.
