If you’re looking for something to look forward to this fall, we have a very convincing one: the annual Sleepy Hollow Street Fair is heading back to Beekman Avenue this September, bringing 145+ vendors, local food, live entertainment, Halloween-inspired finds, and the Headless Horseman himself to the Hudson Valley.
Each year, as the leaves begin to change and Halloween approaches, the Hudson Valley town comes alive with celebrations of its community, history, and spooky roots. For one day, the village’s main drag will become a giant pedestrian party, with cars kicked to the curb and thousands of visitors in attendance.
Known locally as the “unofficial opening bell for autumn,” it makes for a pretty fitting way to kick off the season in one of New York’s most famous Halloween towns.
Even better? Admission is completely free! Here’s everything you need to know about getting spooky season off to a frighteningly good start.
👻 Why is Sleepy Hollow associated with Halloween?
You can thank Washington Irving for a lot of Sleepy Hollow’s spooky reputation.
The village became forever linked to Halloween lore thanks to Irving’s 1820 classic, The Legend of Sleepy Hollow, which brought the infamous Headless Horseman and the Hudson Valley setting to literary fame. Irving was inspired by the area’s landscape, folklore, and ghost stories, and several real Sleepy Hollow landmarks appear in the tale.
That includes the Old Dutch Church and Burying Ground, founded around 1685, which appears in Irving’s story and is associated with the legend of the Headless Horseman.
Nearby Sleepy Hollow Cemetery is also the final resting place of Irving himself, along with notable figures including Andrew Carnegie, William Rockefeller, Walter Chrysler, and Elizabeth Arden, just to name a few.
So, yes, a giant fall street fair filled with Halloween merch and a Headless Horseman appearance feels pretty on brand.
🎃 What to expect at the Sleepy Hollow Street Fair
On Sunday, September 20, 2026, Beekman Avenue will completely close to vehicular traffic from 10 am to 5 pm. Thousands of visitors are expected to fill the streets for a full day of shopping, eating, and seasonal festivities.
Along Beekman Avenue, you’ll find:
- 145+ Craft & Artisan Vendors: Shop handmade jewelry, ceramics, candles, prints, woodwork, vintage finds, clothing, crystals, art, and plenty of witchy and Halloween-themed goods
- Hudson Valley Eats: Food trucks and stalls serving wood-fired pizza, lobster rolls, hot pretzels, kettle corn, soft serve, and authentic Peruvian and Greek dishes
- Live Music & Performances: Catch acoustic music duos along Beekman Avenue, plus a special performance by Luis Enrique’s Andean Flutes Band in the main parking lot
- Witches Along the Hudson: Watch the popular spooky dance spectacle popping up at Beekman Avenue and Pocantico Street (performances at 11:30 am and 3 pm)
- Family & Kids’ Zone: Dedicated kids’ activities and face painting held in the main Beekman parking lot
- Local Village Shops: Brick-and-mortar storefronts along the street will prop their doors open with special fair-day offerings
👀 The Headless Horseman is coming, too
Perhaps the most appropriately spooky part of the whole thing? The Headless Horseman himself will be making an appearance in his finest creepy cape.
He’ll be stationed near the corner of Beekman Avenue and Broadway/Route 9, outside Ganso Ramen & Sushi, so you really can’t miss him. Well, technically, you could miss his head.
🍂 Make a fall weekend of it
If you’re coming all the way from NYC, why not make a weekend of it?
Sleepy Hollow and nearby Tarrytown are packed with fall-friendly things to do beyond the street fair.
Start with a stroll through Sleepy Hollow Cemetery or visit the Old Dutch Church, which famously appears in The Legend of Sleepy Hollow.
You can also explore Lyndhurst Mansion, where Fall Crafts at Lyndhurst will bring 200+ makers to the estate from September 18–20.
🏚️ Where to stay near Sleepy Hollow
For an easy overnight, Tarrytown is a great home base, with several hotels just a short drive from Sleepy Hollow and easy access to Metro-North. Nearby options include”
- Tarrytown House Estate: A historic property surrounded by 19th-century architecture and greenery, about 2.5 miles from downtown Tarrytown and roughly 3.5 miles from Sleepy Hollow
- Sleepy Hollow Hotel & Conference Center: Located about two miles from Sleepy Hollow, with an indoor pool and fitness center
- Courtyard by Marriott Tarrytown: A more modern option about 2.5 miles from Sleepy Hollow, with an indoor pool and fitness center
- Sheraton Tarrytown Hotel: A full-service hotel about three miles from Sleepy Hollow with an indoor pool, spa, fitness center, and on-site dining
- SpringHill Suites by Marriott Tarrytown: A good option if you want more space, with complimentary breakfast and suite-style accommodations
Basically, make the street fair your Sunday plans and give yourself the rest of the weekend to explore one of New York’s most delightfully spooky towns.
📍 Sleepy Hollow Street Fair 2026 details
- What: The Sleepy Hollow Street Fair
- When: Sunday, September 20, 2026 | 10 am – 5 pm
- Where: Beekman Avenue (between Pocantico Street and Broadway/Route 9), Sleepy Hollow, NY
- Cost: Free admission (Pay-as-you-go food, drinks, and vendors)
- Weather: The fair is scheduled to take place rain or shine
🚆 How to get to there from NYC
Taking public transit is by far your best bet. Between heavy event traffic, street closures on Beekman Avenue, and extremely limited local parking, leaving the car behind is significantly less stressful.
- By Train: Hop on the Metro-North Hudson Line from Grand Central Terminal to Tarrytown Station (about 35 minutes on express trains). From there, take a short walk or quick rideshare straight to Beekman Avenue. You can also take the train to Philipse Manor Station, depending on your schedule.
- By Car: If you drive, skip trying to park near the fairgrounds—Beekman Avenue will be closed off. Expect heavy delays and plan to park in municipal lots or side streets farther out, then walk in