Which Saturday in the next five weeks should you keep clear? In Larchmont this year, the answer is December 5. Most of what happens between now and then is the run-up to it.
The Larchmont Chamber of Commerce's 2026 holiday program runs from Friday, November 13 through Saturday, December 12. That's a month. Look at the dates inside it, though, and the calendar keeps pointing at the first Saturday of December. The shopping raffles start the clock. A church bazaar in its hundredth year marks the halfway point. A contest that starts in November gets judged that Saturday. A tree-lighting tradition belongs to that Saturday by definition.
Here is the full season, date by date.
| Date | What | Where |
|---|---|---|
| Fri., Nov. 13 to Sat., Dec. 12 | Shop Larchmont raffle program | Participating local businesses |
| Sun., Nov. 15 to Sat., Nov. 21 | St. John's online silent auction | Online, with items displayed at the Bazaar |
| Fri., Nov. 20 | Gingerbread Contest kick-off | Larchmont Chamber of Commerce program |
| Sat., Nov. 21, 10 a.m. to 3 p.m. | St. John's 100th Annual Christmas Bazaar | 4 Fountain Square, Larchmont Manor |
| Sat., Dec. 5, 10 a.m. to 3 p.m. | Holiday Stroll, plus gingerbread voting and prizes | Business districts across town |
| First Saturday of December, evening | Light Up Larchmont | Constitution Park |
| Every Saturday, 8:30 a.m. to 1 p.m. | Down to Earth Larchmont Farmers Market | Metro-North upper lot off Chatsworth Avenue |
Friday Starts the Clock on Palmer and Chatsworth
Shop Larchmont opens Friday, November 13. The Chamber designed it so that holiday spending at local businesses doubles as a raffle entry. Participating storefronts, restaurants, service businesses and online shops display signage with a QR code. Any time you make a purchase during the program, you can scan it and enter. The Chamber raffles off multiple prizes every week until the program closes on December 12.
The prizes are worth paying attention to. The Chamber asks that each donated raffle prize be worth at least $100. This year also brings a new digital gift guide, and each participating business can put one item in it. Because the drawings happen weekly, a coffee in mid-November can win just as easily as a gift bought in December. Starting your local shopping early simply means more entries.
A Bazaar That Has Been Doing This Since 1926
The most important date before December falls on Saturday, November 21. That day, St. John's Episcopal Church hosts its 100th Annual Christmas Bazaar at 4 Fountain Square in Larchmont Manor, from 10 a.m. to 3 p.m., with free admission. The Larchmont Ledger opens its November preview this way:
"A beloved community tradition reaches a milestone this year as the St. John's Christmas Bazaar celebrates its 100th anniversary!"
The bazaar started with the St. John's Episcopal Church Women, who founded it in 1926, according to Patch. Its purpose is the same as it was then. Money raised supports local nonprofits serving women and children in need. Over the past five years, proceeds have provided more than $200,000 in Episcopal Church Women's Outreach Grants. In 2026 alone, 22 organizations received grants, among them Community Counseling Center, Community Resource Center, The Sharing Shelf, Boys & Girls Club of New Rochelle, Youth Shelter of Westchester and Interfaith Prison Partnership.
The tables cover just about everyone on a holiday list: collectibles, handcrafted pieces, holiday decorations, jewelry, gently used toys, children's books, sporting equipment, and sweet and savory treats. Through the day there's live entertainment, children's activities, a visit from Santa Claus and a food truck serving lunch.
The silent auction opens first. It runs online from Sunday, November 15 through the day of the Bazaar and features tickets to sports, music and theater events along with other items and experiences. The items are on display at the Bazaar, and online bidding stays open all day. St. John's will post the auction link and a QR code closer to the event on its Christmas Bazaar page. For questions, call (914) 834-2981.
The bazaar falls the day after another nonprofit-driven tradition gets underway.
The Gingerbread Houses Get Built Now and Judged Later
The Chamber's Holiday Dream Home Gingerbread Contest kicks off Friday, November 20, and voting and prizes come on Saturday, December 5. The teams are the Chamber's nonprofit members, and they compete for one of three cash prizes. A professional coach guides each team. This year's theme is "What do the holidays mean to you?", and each organization is asked to use it to tell its own story, whether that means its traditions, its service programs or its moments of connection.
Last year's format gives a sense of how your vote counts. In 2025, a judging panel picked first and second prize based on creativity, sturdiness and individuality, and the community vote decided third prize. In-person voting ran across two days that year, and the winners were announced at 2 p.m. during the Holiday Stroll. This year voting and prizes fall on a single day, the same day as the Stroll. The Larchmont Chamber of Commerce posts the viewing and voting details.
So the gingerbread contest starts in November, and so does Shop Larchmont. Both reach their main payoff on December 5.
December 5, Morning to Night
That Saturday is the first Saturday of December, and the Village of Larchmont schedules its daytime and evening holiday traditions around that day. Here's how the day lines up:
- 8:30 a.m. to 1 p.m. The Down to Earth Larchmont Farmers Market runs as usual. It's open every Saturday year-round in the Metro-North upper lot off Chatsworth Avenue, and the Village directs visitors to enter via Myrtle Boulevard.
- 10 a.m. to 3 p.m. The Chamber's Holiday Stroll fills the business districts. The community can stroll, shop, sample treats and join holiday activities inside businesses and outdoors. Tasting stops appear on the event map. Horse-drawn carriages return to give rides through town.
- During the Stroll. Gingerbread voting and prizes.
- To close the Stroll. Santa arrives on a fire truck, with a police escort, courtesy of the Larchmont Professional Fire Fighters Association and the Larchmont PBA.
- Evening. The Village lists Light Up Larchmont at Constitution Park on the first Saturday of December. The same two groups that bring Santa in, the Larchmont Professional Fire Fighters Association and the Larchmont Police Benevolent Association, organize and sponsor it.
The firefighters and PBA end the daytime Stroll with Santa, and then they host the evening lighting in the park. That makes it one long day with a hand-off in the middle. Last year worked the same way. Village board minutes from December 1, 2025 list Light Up for Saturday, December 6, from 3 to 6 p.m., which was the same day the gingerbread winners were named at the Stroll. If you have guests in town that weekend, this is the day to bring them.
The Village also lists the annual Menorah Lighting at Constitution Park. Chabad of Larchmont-Mamaroneck organizes and sponsors it, and it is typically held on a Thursday or Sunday of Hanukkah.
The Week After, the Raffle Is Still Running
December 5 is the big day, but the program keeps going. Shop Larchmont runs for one more week, through Saturday, December 12, with its weekly drawings still going. Any errands you put off until after the Stroll still earn entries. The farmers market is open that Saturday too, same lot and same hours.
Count backward and the season's two key Saturdays are clear. November 21 is the Bazaar in Larchmont Manor. December 5 is everything else. Both are worth putting on your calendar this week.
I've walked this calendar for a long time, and if the Stroll gets you curious about what your own house would bring in today's market, Elka Raved can put together an Instant Home Valuation for you in the quiet days between December 5 and the new year.
