Between October 31 and November 1, two familiar North Fork farm calendars come to an end. On that same Sunday, November 1, the Cutchogue New Suffolk Free Library holds a history lecture. For the next five weeks Cutchogue's shared calendar is set mostly by two nonprofit neighbors on Main Road: the library at 27550 Main Road and the Cutchogue-New Suffolk Historical Council & Museums on the Village Green at 27320 Main Road. Their programs build week by week, and the last of them all fall on Sunday, December 6.
The turn happens over one weekend
Across the area's farm stands, the weekend of October 31 is when the season starts closing. Newsday's 2026 Long Island farm stand guide lists Krupski's Farm on Route 25 in neighboring Peconic as open daily September 1 through October 31. Harbes Orchard in Mattituck lists daily hours through November 1.
On November 1, Main Road in Cutchogue has an indoor program instead. The library and the Historical Council are co-sponsoring "Jefferson & Madison's Tour of Long Island 1791," a lecture by Professor John S. Kneski, on Sunday, November 1, from 2:00 to 3:30 p.m. at the library. Registration is required. Anyone carrying a Suffolk County 250th Passport Book can get it stamped at the event.
The same day, Cutchogue's best-known farm stand starts its Thanksgiving business. Wickham's Fruit Farm says it starts taking Thanksgiving pie orders on November 1. Orders are due the Friday before the holiday, and you can place them in person at the stand or by phone. The stand is closed on Sundays, so this year the first day you can order at the counter is Monday, November 2.
The November calendar, by date
Most of the month's shared events happen at the library's gallery and the Village Green. The library lists registration as required for each of its own programs below.
| Date | What | Where | Detail |
|---|---|---|---|
| Sun, Nov 1, 2:00–3:30 p.m. | Jefferson & Madison's 1791 Tour lecture | Cutchogue New Suffolk Free Library | Co-sponsored by the library and the Historical Council; registration required |
| Sat, Nov 7, 2:00 p.m. | Annual Fall Concert, Trio Azura | Library | Registration required; reception in the art gallery afterward |
| Sun, Nov 8 | VIP blending session | Sannino Vineyard, 15975 County Route 48 | Listed on the winery's event calendar |
| Fri–Sun, Nov 13–15 | Christmas Pop-Up grand opening | Carriage House, Village Green | Then open weekends through Dec 6 |
| Sat, Nov 21, 2:00 p.m. | Christiaan Padavan | Library | Registration required; reception afterward |
| Sun, Dec 6 | 5K, holiday concert, pop-up's final day | Cutchogue–New Suffolk | Details below |
Trio Azura is the biggest booking of the month. The library's Fall 2026 newsletter says the trio won the 2025 Young Concert Artists Susan Wadsworth International Auditions and became that organization's first Ensemble-in-Residence. The Carole Donlin Charitable Foundation is sponsoring the November 7 concert, and a meet-the-artists reception follows in the art gallery.
The November 21 concert is closer to home. Christiaan Padavan is a Long Island singer-songwriter who, according to the library, won a Golden Ticket to Hollywood on Season 17 of American Idol by singing Billy Joel's "Vienna." His set covers pop, jazz, soul and classic standards. Both concerts are on Saturdays at 2:00 p.m. and both require registration, so popular programs can reach capacity before the day.
Main Road businesses that stay open
While the nonprofits take over the shared calendar, several Cutchogue farms and tasting rooms keep running with longer seasons than many people expect.
Wickham's, at 28700 Main Road, describes its usual season as May through December. Hours are 9 a.m. to 5 p.m., Monday through Saturday, and the stand is closed on Sundays, Thanksgiving Day and Christmas. Apple, apple crumb, Orchard Harvest, peach crumb and strawberry rhubarb pies are baked daily at the stand. Pumpkin and pecan are seasonal pies.
Newsday's 2026 guide lists Oregon Road Organics, at 12595 Oregon Road, as open through Thanksgiving. The farm also advertises Thanksgiving Harvest Boxes on its own site. Its posted stand hours there are different from Newsday's listing, so check the farm's site before you go.
Pellegrini Vineyards at 23005 Main Road keeps its tasting room open seven days a week, all year. It closes only on Mother's Day, Easter Sunday, Thanksgiving, Christmas and New Year's Day. Up on Oregon Road, Rooted North, formerly Lieb Cellars, has posted its 2026 holiday schedule.
Here is how Thanksgiving week works out on Main Road and Oregon Road:
- Friday, November 20: last day to order a Thanksgiving pie from Wickham's, based on its "Friday prior" deadline.
- Thursday, November 26: Wickham's, Pellegrini and Rooted North are all closed for Thanksgiving.
- Friday, November 27: Rooted North's tasting room at 13050 Oregon Road reopens at noon.
If you're hosting relatives for the long weekend, that means a Friday tasting room is open on Oregon Road and the Main Road farm stand is back to its regular hours.
The Carriage House pop-up runs the second half of the season
The Historical Council's Christmas Pop-Up is the longest-running event on this calendar. It opens November 13 with a three-day grand opening at the Carriage House on Cases Lane, behind the Village Green. After that it is open every weekend through December 6: Fridays 11 a.m. to 6 p.m., and Saturdays and Sundays 10 a.m. to 5 p.m.
According to the Council's event page, the shop sells traditional, vintage, Victorian and donated decorating items and gifts, and serves Christmas teas and treats while you browse. New this year is a large collection of vintage and antique Tavern and Gurley holiday candles, between 60 and 90 years old. The Council advises coming early for the best selection. All proceeds go to the nonprofit Council, and questions go to [email protected].
The pop-up keeps the Green busy for four straight weekends, from mid-November into December. The Council stewards the historic houses on the Green, so it's fitting that the season's longest-running event takes place there, a few steps from the library.
December 6, when everything lands on one day
Four separate hosts have events on Sunday, December 6.
- 10 a.m. to noon: the Cutchogue Fire Department's 14th Annual Stuff the Sleigh 5K and Toy Drive in Cutchogue–New Suffolk, listed on the department's events page.
- 10 a.m. to 5 p.m.: the last day of the Christmas Pop-Up at the Carriage House.
- 2:00 p.m.: the library's Annual Holiday Concert with the House of the Red Hart Singers, an eight-member a cappella group, followed by a holiday reception in the gallery. Registration is required.
- Also that day, Sannino Vineyard has its Wine Club holiday party on its calendar.
You can do all of it in one day. Run or walk the 5K in the morning, stop at the Carriage House before it closes for the season, and be at the library by 2:00 for the concert.
If you're new to the hamlet and want to know more about it, our Cutchogue neighborhood guide covers the year-round picture. Our late-summer weekend in Cutchogue covers the busiest stretch of the farm season. The library also serves New Suffolk, and our post on how New Suffolk's civic life works shows how the two hamlets share it.
At Cheryl & Regan, we keep a close eye on Cutchogue's calendar through the off-season. If you're hosting family for Thanksgiving or planning a winter on the North Fork and want a local's take on where to go, we're happy to talk it through over coffee, or about your home whenever you're ready.
