"As you know, Mother Nature hasn't made scheduling easy this season, but third time's a charm," Sleepy Hollow Chamber of Commerce Executive Director Lucia Ballas-Traynor said when she announced the new date, according to River Journal. She described the rescheduled fair as "a grand finale for autumn," one that keeps "the fun of Spooky Season alive while kicking off early holiday shopping and festivities."
That third date is this Sunday, November 8, from 10 a.m. to 5 p.m. In past years the street fair was one more weekend inside the October rush. This year it falls eight days after Halloween, so the fair does two jobs on the same day: it is the last day of the spooky season on Beekman Avenue and the first holiday shopping day on that same stretch of sidewalk. For anyone in Sleepy Hollow Manor, the village's main commercial street is about to have the busiest Sunday it has seen since October.
How a fall fair ended up in November
The 2026 fair got this late one rainout at a time.
- The original September weekend. Rained out, according to River Journal's report, which describes "two successive weekend rainouts."
- Sunday, September 27. This was already a makeup date, and the Village of Sleepy Hollow calendar shows it cancelled because of a severe weather forecast.
- Sunday, November 8. This is the date now posted on the Chamber's street fair page, labeled "NEW DATE."
Compare that with recent years. The village calendar listed the 2024 Beekman Avenue Street Fair on October 5, 2024, and the 2023 fair was also held in October, after its own weather postponement. Those fairs ran in the middle of the busiest weeks of the village's year. A November date puts the fair after that peak. It's the same event at a different point on the calendar.
That matters because of the fair's size. River Journal reports that it draws some 20,000 people to the village each year. In past years that crowd came in October, along with everything else the season brings to the village. This year it comes in November.
The Horseman still rides, one week late
The November schedule opens with witches and a storyteller and gives the Headless Horseman a three-hour stretch at the top of the avenue. The live music in the table comes from the BUMP, the band that presents the fair's music lineup and also plays a set.
| Time | Act | Where |
|---|---|---|
| 10:00 a.m. | Fair opens | Beekman Avenue, Pocantico Street to Route 9 |
| 11:00 a.m. to noon | Scoot and Marlena of The Kulprits | Beekman parking lot entrance |
| 11:30 a.m. | Witches Along the Hudson | Beekman Avenue and Pocantico Street |
| Noon | Jonathan Kruk, Master Storyteller | In front of Ganso Ramen, Beekman and Route 9 |
| 12:15 to 1:15 p.m. | Polish John | Beekman parking lot entrance |
| 1:00 to 4:00 p.m. | The Headless Horseman | In front of Ganso Ramen, Beekman and Route 9 |
| 1:30 to 2:30 p.m. | the BUMP | Beekman parking lot entrance |
| 2:45 to 3:45 p.m. | The Altogether | Beekman parking lot entrance |
| 3:00 p.m. | Witches Along the Hudson | Beekman Avenue and Pocantico Street |
| 4:00 to 5:00 p.m. | Brad & Nate, The Incumbents Acoustic | Beekman parking lot entrance |
Luis Enrique's Andean Flutes Band will play in the Beekman lot at the top of Beekman and Route 9, and the Village of Sleepy Hollow Kids' Zone is in the Beekman parking lot. The Visit Sleepy Hollow guide adds face painting and music duos at the top, middle and bottom of the avenue.
The schedule is laid out so the two ends of the route have different jobs. Most of the Halloween acts are at the Route 9 end, around Ganso Ramen and the Beekman lot. The witches are at Pocantico Street, at the other end. Families who come for the Horseman can catch Jonathan Kruk at noon and stay near Broadway for the next three hours, while the music continues at the lot entrance right beside them.
The holiday half is already on Beekman Avenue
Ballas-Traynor's mention of "early holiday shopping" refers to more than the vendor tents. The Chamber's own fair page lists the year-round businesses along and around the route. River Journal describes the day as one with "local shops with their doors propped open" and Beekman closed to cars. Here are those businesses, ordered by address from the Broadway end:
- Ganso Ramen & Sushi, 3 Beekman Avenue, the Horseman's corner
- J & G Italian Deli, 23 Beekman Avenue
- Quality High Cannabis Boutique, 25 Beekman Avenue
- The Taco Club and Cozy Coven, both at 31 Beekman Avenue
- J.P. Doyles Restaurant, 48 Beekman Avenue
- Sabrosura Peruana, 62 Beekman Avenue
- Casaletto Pizza, 70 Beekman Avenue
- I Scream, 72 Beekman Avenue
- Honey & Gold Flower Shop, 74 Beekman Avenue
- Coco Taqueria, 84 Beekman Avenue
- Justin's Deli & Cafe, 86 Beekman Avenue
- Beekman Ale House, 92 Beekman Avenue
- Sleepy Hollow Bookshop and The Village Confectionery, both at 95 Beekman Avenue
- Sleepy Coffee, Too, 110 Beekman Avenue
- Tumbao Latin Bar & Lounge, 111 Beekman Avenue
For holiday shopping, look at the shops in the middle of that list. A flower shop, a bookshop, a candy shop sharing the bookshop's address, and Cozy Coven make up a short gift run that the Chamber has put directly on the fair route. The Chamber's list also reaches beyond Beekman. It includes Los Andes Bakery at 180 Valley Street, Santorini Greek Restaurant at 175 Valley Street, ChuChok Thai at 404 Old Broadway and DeCicco & Sons at 1 Legend Drive.
On top of the storefronts, the fair brings more than 145 arts and crafts, food and beverage vendors. The vendor list includes Cousin's Maine Lobster, Brothers Fish & Chips, George's Wood Fire Mobile Pizza, All Heart Baking and Andreacello's Chocolate Cello. Cooper's Daughter Spirits/Olde York, Freefall Sangria and Manor Sangria will pour drinks. Sleepy Hollow Cinema is listed among the participating nonprofits, alongside Phelps Hospital/Northwell Health, which is the fair's presenting sponsor.
The newest table in town gets its first street fair
The fair schedule doesn't mention it, but one Beekman Avenue restaurant will see its first Sleepy Hollow Street Fair this year. The Hudson Independent reported that North River Oyster Bar opened at 222 Beekman Avenue on May 19, 2026, in the former Hudson Anchor space. It is the third restaurant from Floria and Gino Uli, who also own Divino Cucina Italiana in Hastings and Hudson Prime Steakhouse in Irvington. The paper described the space as a "narrow two-floor-plus-rooftop restaurant" that took about two years of permits and a gut renovation to open. In the same article, Floria Uli described the village this way: "People walk around, and it's really a happening vibe."
Because it opened in May, November 8 will be its first street fair. Its website currently lists Tuesday through Sunday hours of noon to 10 p.m., which would keep it open after the fair ends at 5. Hours can change, so check the site before you plan dinner around it.
Getting to a street that is closed to cars
Beekman Avenue will be closed to traffic for the whole day between Pocantico Street and Broadway/Route 9. The fair is free, needs no tickets or registration, and goes ahead rain or shine. After two rainouts, "rain or shine" is the important part. The Chamber has asked visitors to follow its Instagram feed for updates.
The Visit Sleepy Hollow guide recommends parking off the fair route and walking in. It points drivers to metered parking on nearby streets and to municipal lots in neighboring Tarrytown. It also has a guide to visiting Sleepy Hollow without a car for anyone with guests coming by train. Dogs are welcome. The guide suggests allowing about two hours to walk the whole avenue, and lists the Sleepy Hollow Tarrytown Chamber of Commerce at 914-538-3156 for questions.
For Sleepy Hollow Manor residents, the same closure works in reverse. Any errand that normally runs down Beekman Avenue between 10 and 5 on Sunday will need another route. Meanwhile, the crowd heading for the Horseman will collect at the Route 9 end, where Beekman meets Broadway.
If a Sunday on Beekman Avenue has you thinking about how much a walkable village center adds to a home's value, the Aloia Stroub Team follows Sleepy Hollow's streets closely, through the busy seasons and the quiet ones. When you're ready to see what your Sleepy Hollow Manor home is worth, request a free home valuation and we'll go through the numbers with you.
