Irvington's December Runs Out on the 20th
November 12, 2026
November 12, 2026
Washington Irving's Sunnyside closes for the season on Sunday, December 20. Everett Bradley's HOLIDELIC plays Irvington Theater that same afternoon, and the library's best-loved December concert is the day before. Irvington's holiday season starts on the weekend of November 20 and gets shorter as it goes. Sunnyside's hours set the pace: it is open Friday through Sunday until November 29, then Saturdays and Sundays only from December 5 to December 20. The village's own events, the theater's holiday shows and the library's programs all fall inside those weekends, so each weekend holds more than it would if they were spread out.
So the useful way to plan the season is by weekend, and there are fewer of them than you might expect.
The first thing on the calendar is Friday, November 20, at 4 p.m. That is when online registration closes for the Peter K. Oley Turkey Trot, which Irvington Recreation & Parks runs on Sunday, November 22. You can only register online, and there is no race-day sign-up. Fees are $25 for resident youth 16 and under and $30 for resident adults 17 and over. Nonresidents pay $30 and $35.
Runners start in the Dows Lane School parking lot, go left onto Broadway inside the barricades, then left onto Sunnyside Lane and left again onto the aqueduct. They follow it straight across Main Street and finish in Memorial Park. In 2.5 miles, the race passes the lane to Irving's estate and crosses the street where the theater, the bakery and most of the season's other stops are.
Race-day timing, from the Village's notice:
The race is held rain or shine, and entry fees are not refunded. The name has local history behind it. The Village's tribute calls Peter K. Oley the "Godfather of Running." He coached Irvington High School track and cross-country for 50 seasons, from 1956 to 2005, and helped create the Turkey Trot.
The same weekend, the theater offers an indoor option. Broadway Training Center of Westchester brings Come From Away to Irvington Theater, billed as a Rivertowns Premiere. Shows are Friday, November 20 at 7 p.m., Saturday, November 21 at 7 p.m., and Sunday, November 22 at 3 p.m. The theater's page describes BTC as its longest-running Arts Partner and says the school has been making theater for 35 years. The Sunday matinee starts an hour after the race, so runners can go from the Memorial Park finish to their theater seats with some time to spare.
Sunnyside is open all three days of this weekend too. Historic Hudson Valley's ticket calendar lists tours on November 20, 21 and 22.
The fall Legendary Tours at Sunnyside ended November 8, and the estate went back to its regular Friday-to-Sunday schedule. The calendar lists tours on November 27, 28 and 29, the Friday, Saturday and Sunday after Thanksgiving. Those are the last Friday hours of the year. After that weekend, the estate is open only on Saturdays and Sundays.
That matters if you host family over Thanksgiving. If you want to take guests through Irving's cottage on a weekday-adjacent visit, Friday, November 27 is the last chance. The full calendar is on Historic Hudson Valley's Sunnyside page, and its admission section says tickets cost $2 more when bought on the day of the visit.
Saturday, December 5 is the first weekend-only day at Sunnyside. It is also the date of the Village's Holiday Happening, which Parks and Recreation listed on its 2026 special events schedule back in August. Times and the program will be posted on the Village of Irvington's website.
That evening at 7 p.m., the Hudson Valley Singers perform Peace on Earth, an international Christmas concert, at Irvington Theater. The theater's listing says the chorus is coming back after its holiday show last year. The program includes carols from Poland, Argentina, Lebanon and Wales, along with arrangements by Vaughan Williams. The group has sung choral music in the region for 75 years under music director Eugene Sirotkine. It is a non-auditioned chorus, and its members range from students and teachers to doctors and CEOs.
So in one day you could tour the estate, go to the village's holiday event and hear an evening concert. It is the busiest single date on the calendar, and it comes right as Sunnyside's hours shrink.
The weeks between December 5 and the last weekend are quieter, but not empty. On Saturday, December 12, Amanda Kupillas Dance puts on The Nutcracker at Irvington Theater, with shows at 11 a.m. and 3:30 p.m. Sunnyside is open that weekend too, as one of its Saturday-and-Sunday days.
The Irvington Public Library has two midweek programs aimed at specific audiences. Gingerbread Man Storytime is Tuesday, December 15 at 4 p.m. A seniors' screening of A Muppet Christmas Carol is Friday, December 18 at 10:30 a.m. Both are on the library's December calendar.
The last weekend has the two events with the most history behind them.
On Saturday, December 19, from 2 to 4 p.m., the John Lang Trio plays Vince Guaraldi's music from A Charlie Brown Christmas in the library's Program Room. The library calls it a beloved annual tradition that is coming back "after a one-year hiatus." It is listed under adult, children's and teen programs, so the whole family can go.
On Sunday, December 20 at 3 p.m., Everett Bradley's HOLIDELIC plays Irvington Theater. That is also Sunnyside's last open day of 2026. A morning at Irving's estate followed by an afternoon at the theater is the latest a holiday day like that can happen in Irvington this year.
One new business will be open for every one of these weekends. The Hudson Independent reported that Bliss Bakehouse opened on Main Street in May 2026, so this is its first holiday season. The paper describes it as the long-planned project of married couple Alison Stinson and Jason Breen. The bakery is at 94 Main Street. In that article, Stinson said the couple "walked the streets of Irvington, chatting with neighbors and businesses" before opening, to learn what the village needed.
The Hudson Independent's review mentions an Oreo-stuffed chocolate chip cookie, a caramel apple pie bar, macarons and a vegan chocolate chip cookie. Savory options include croissants, bagels with a gluten-free choice, and empanadas with homemade hot sauce. Brunch is served all day on Saturdays and Sundays, including a savory croffle and a kids' menu that comes with crayons and an activity book. Since the season happens almost entirely on weekends, all-day weekend brunch lines up well with it. It can work before the Nutcracker matinee, after the Turkey Trot crosses Main Street, or between a Sunnyside tour and a 3 p.m. curtain on December 20.
Put together, every date on this calendar falls in the month from November 20 to December 20. The Turkey Trot route connects the places on the map, and Sunnyside's schedule sets the end date.
Seasons like this one, with a Turkey Trot named for a 50-season coach and a Charlie Brown concert back after a year off, are part of why I've stayed in this part of Westchester for so long. If you're thinking about how your own plans fit Irvington's calendar, whether you're hosting family this December or planning a sale for spring, Lena O'Neill would be glad to help. Schedule a free consultation, and we'll go over your timing together.
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