Sleepy Hollow Street Fair

Beekman Avenue closes to cars, fills with 145 vendors, and Sleepy Hollow starts its Halloween season.

The Street Fair is the village’s unofficial opening bell for autumn — a free, walkable Sunday on Beekman Avenue with the whole street given over to arts and crafts stalls, food trucks, local shops with their doors propped open, and a good deal of Halloween merchandise arriving a full six weeks early.

Presented by the Sleepy Hollow Tarrytown Chamber of Commerce, it’s the rare fall event here that costs nothing, needs no ticket, and welcomes dogs.

What you’ll find

• 145+ vendors selling handmade jewelry, ceramics, candles, prints, woodwork, vintage, and a deep bench of witchy and Halloween-themed goods
• Food and drink from local eateries and visiting vendors — wood-fired pizza, lobster rolls, pretzels, kettle corn, soft serve, Greek, Peruvian, and sangria and spirits for the grown-ups
• Live music from duos stationed at the top, middle, and bottom of Beekman, plus an Andean flutes band in the Beekman lot
• The Headless Horseman, posted near the corner of Beekman and Broadway (Route 9), outside Ganso Ramen
• Witches Along the Hudson at Beekman and Pocantico Street
• A Kids’ Zone in the Beekman parking lot, plus face painting

Know before you go

• When: Sunday, September 20, 2026, 10 am to 5 pm. Street fair is rain or shine so dress for the weather!
• Where: Beekman Avenue, Sleepy Hollow, between Pocantico Street and Broadway (Route 9)
• Cost: Free. No tickets, no registration.
• Dogs: Welcome, and plenty come. Bring water on a warm September day.
• Getting there: Beekman Avenue is closed to traffic for the day, so plan to park off the fair route and walk in. There is metered parking on nearby streets as well as municipal lots in adjacent Tarrytown. Coming by rail is easy — see our guide to visiting Sleepy Hollow without a car.
• Best for: Browsers and grazers. Come hungry, bring a tote, and give yourself two hours if you want to make it up and down the whole avenue.
• Questions: Sleepy Hollow Tarrytown Chamber of Commerce, 914-538-3156

Make a weekend of it

The village’s shops, galleries, and antique stores are open too, and Fall Crafts at Lyndhurst runs Friday through Sunday, September 18–20, three miles south — 200+ makers, tickets from $13. Both run 10 to 5 on Sunday, so catch the craft show Friday or Saturday and keep Sunday free for Beekman Avenue. It all kicks off Halloween in Sleepy Hollow Country.