Last year the Pound Ridge Business Association held its Holiday Market on December 6, 2025, nine days after Thanksgiving. This year it is on Saturday, November 21, 2026, five days before the holiday. With the market in November, the town's public holiday events now sit on two Saturdays three weeks apart. The market opens the season, and almost everything else is on December 12.
That makes the calendar easy to plan. One weekend in Scotts Corners comes before the turkey. One long Saturday comes in mid-December, starting with gingerbread at 10 a.m. and ending with a lit tree around 5 p.m. Most of what happens in between is ordering ahead.
Two Dates, One Season
The move changes where the market falls relative to everything else on the town calendar.
| 2025 | 2026 | |
|---|---|---|
| Holiday Market date | Saturday, December 6 | Saturday, November 21 |
| Relation to Thanksgiving | Nine days after | Five days before |
| Hours | 10 a.m. to 4 p.m. | 10 a.m. to 4 p.m. |
This year the market comes three weeks before the Candy Cane Run. Gifts bought on the Village Green on November 21 can be wrapped before Thanksgiving dinner, and December 12 is left to the Town's own events.
What November 21 Puts on Westchester Avenue
The market is on Westchester Avenue, and the Business Association's calendar lists it at 77 Westchester Avenue. The Town of Pound Ridge identifies that address as the Village Green within the Scotts Corners Parking District. The organizers promise local vendors, food and music.
Last December's lineup gives a sense of the mix. It included two spirits makers, Croton Dam Spirits and Cooper's Daughter, along with Colliers Candle Company, Stark Vintage, Always in Bloom CT, Elysian Jewels NYC, Knits and Stripes, Krop Jeans, M Murphy Art & Design, Berete Collectible African Art and Jones Music NYC.
The Village Green sits in the middle of the shops that line Scotts Corners, so a market visit is also a walk past most of the hamlet's storefronts. Within a short stretch of Westchester Avenue:
- Booksy Galore, 67 Westchester Avenue, sells new, used and vintage books and vinyl. Its fall hours on Saturdays run 10 a.m. to 6 p.m., and its gift shelf includes a New York holidays title.
- The Cottage, also at 67, carries vintage and new decor, clothing, candles and jewelry.
- The Kitchen Table, 71 Westchester Avenue, is a farm-to-table cafe.
- Breads N Bakes, 73 Westchester Avenue, is a bakery. It comes up again on December 12.
- 123 Dough, 78 Westchester Avenue, is an organic sourdough bakery. Its storefront opens at 9 a.m. on Saturdays and stays open until 8 p.m.
- Chubby's Hardware, 64 Westchester Avenue, is a full-service hardware store, useful when the extension cord for the outdoor lights gives out.
- The Market at Pound Ridge Square, 55 Westchester Avenue, has a bakery, deli, butcher, seafood counter, floral and gift departments, and is open 7 a.m. to 7 p.m. on weekends.
In June, lohud's photo tour of Scotts Corners showed Booksy Galore, The Cottage and Chubby's Hardware open, and The Kitchen Table serving cyclists who had stopped for coffee. The market adds stalls and music to a block that already has its own regulars.
Thanksgiving Week Runs on Orders
The five days between the market and Thanksgiving are when people order food. In Pound Ridge, two places set the terms.
Pound Ridge Organics, the farm and market at 22 Westchester Avenue, has opened Thanksgiving orders for heritage turkeys and what it calls provisions, including pies, loaves, cookies and cider donuts, all through an online form. The farm keeps a market schedule that changes week to week and posts it on its homepage. Its autumn CSA is running now, and registration for the winter CSA opens after Thanksgiving. A few practical notes from the farm: bring your own bag or box, leave dogs at home because it is a working farm with free-roaming chickens, and expect a 3.5 percent fee on credit card and Venmo payments.
For anyone not cooking, The Inn at Pound Ridge by Jean-Georges, at 258 Westchester Avenue, is offering a three-course Thanksgiving Day prix fixe on Thursday, November 26, at $218 per person, with seatings starting at noon. The Inn has set the same price and format for Christmas Day.
December 12, Hour by Hour
Three weeks later, one Saturday holds most of Pound Ridge's public holiday events. The Pound Ridge Library calendar and the Town Recreation Department's fall and winter events page fit together into a single day:
| Time | Event | Where |
|---|---|---|
| 10 to 11 a.m. | Gingerbread House Workshop with Breads N Bakes | Pound Ridge Library |
| 11 to 11:30 a.m. | Tales & Tots | Pound Ridge Library |
| 1 to 2 p.m. | Family Holiday Happening, "Winter Wonderland Library Show" with Robert Rivest | Pound Ridge Library |
| Afternoon | Candy Cane Run: Mr. Claus, Mrs. Claus and Frosty at five stops around town | Around town |
| 4 p.m. | Final Candy Cane Run stop | The Green |
| Around 5 p.m. | Tree lighting | The Green |
The Town bills this as Pound Ridge's second Candy Cane Run. The Recreation Department, the Pound Ridge Fire Department and the Pound Ridge Police Department organize it together. At each of the five stops, the Clauses and Frosty hand out candy canes and pose for pictures. At the last stop on The Green, Troop 1 and the Cub Scouts sell hot cocoa and hot apple cider, and the library gives a winter reading before the tree is lit. The rain date is Sunday, December 13.
Breads N Bakes also runs the gingerbread workshop on Sunday, December 6, from 10 to 11 a.m. Families who can't make the busy Saturday can take that one instead.
On December 12 the library and The Green take turns, and the gaps line up with lunch and the walk over. A family could go from gingerbread at 10 a.m. to the 1 p.m. show to cocoa at 4 p.m. and stay put until the tree is lit.
After the Tree Is Lit
Once December 12 is over, the calendar gets quieter and the remaining dates are mostly about food and school-break afternoons:
- December 17: Pound Ridge Organics begins its winter CSA, which runs through March 11.
- December 25: The Inn at Pound Ridge by Jean-Georges serves its three-course Christmas Day prix fixe at $218 per person, starting at noon.
- December 28, 2 to 3 p.m.: "Start with Art" with Erin Schirota, a holiday special for children at the library.
- December 29, 2 to 2:45 p.m.: "Holiday Animals with The Stamford Museum & Nature Center."
- December 30, 2 to 3 p.m.: The Westchester Children's Museum presents "STEAM Fairy Tales."
All three library specials fall in the same afternoon slot on consecutive days.
Taken together, the season looks like this: the Village Green on November 21, an order to Pound Ridge Organics before November 26, the library and The Green on December 12, and three library afternoons during the week after Christmas.
If you are thinking about a move to or from Pound Ridge in the coming year, William Martin offers a private, investment‑grade consultation that starts with how the town actually works, season by season.
