Events in Sleepy Hollow
September 12-14
Mark your calendars - Fall Crafts at Lyndhurst returns September 12–14, 2025! This three-day festival brings together over 200 artists and makers with original jewelry, fashion, home décor, ceramics, woodwork, photography, and more. It’s the perfect way to spend a September day in the Hudson Valley.
Beyond the shopping, visitors can enjoy gourmet food, craft beverages, live demos, and family-friendly activities like puppet theater and face painting. Admission also includes access to Lyndhurst’s stunning 67-acre grounds, complete with sweeping Hudson River views, gardens, and historic outbuildings.
Fall Crafts at Lyndhurst
September 21
Sleepy Hollow Street Fair
The Sleepy Hollow Street Fair is back on Sunday, September 21, 2025, from 10 am to 4 pm along Beekman Avenue. With over 145 vendors, this fair fills downtown with handmade crafts, food and drink, live entertainment, and plenty of Halloween-inspired finds. Even the Headless Horseman makes an appearance!
Expect a little bit of everything - local shops, artisans, seasonal treats, and fun for the whole family (dogs included). It’s one of the most festive days of the year in Sleepy Hollow and the perfect way to kick off spooky season.
⚠️ Note: The Horseman’s Shop will not have a booth at the fair this year, but you can still shop all our Sleepy Hollow souvenirs online anytime.
Local tip: Parking is extremely tough during the fair (and during the rest of spooky season) - skip the hassle and take the Metro-North Hudson Line to the Tarrytown station, then walk or grab a quick rideshare/taxi into the village.
September 27
Prost! Sleepy Hollow’s 13th Annual Oktoberfest is happening on Saturday, September 27, 2025, from 1–5 pm at Kingsland Point Park. Expect a lively afternoon of German food, local beer, cider, hot chocolate for the kids, and plenty of Bavarian music to keep the energy high.
It’s a family-friendly event with food, drinks, music, and kids’ activities all set against the scenic Hudson River backdrop at the Kathryn Davis RiverWalk Center. Whether you’re raising a stein or just soaking up the atmosphere, Oktoberfest is a perfect way to celebrate fall in Sleepy Hollow.
Sleepy Hollow Oktoberfest
Looking for one of the most magical sights on the Hudson? The 6th Annual SUP Witches Festival splashes into Kingsland Point Park on Sunday, October 19, 2025, from 12–4 pm (rain date October 19). Hundreds of witches and warlocks take to the river on paddleboards, creating one of the most unique Halloween events in Sleepy Hollow.
On land, the park transforms into a spooky celebration with vendors, food, brews, live music, and plenty of Halloween vibes. The Headless Horseman will even make an appearance! Buy Tickets on their website!
⚡ The Horseman’s Shop will be there too! Stop by our booth for Sleepy Hollow souvenirs and spooky-season merch while you enjoy the festival.
📍 Kingsland Point Park, Sleepy Hollow, NY
🗓️ Sunday, October 12, 2025 - 12–4 pm
🌧️ Rain Date: Sunday, October 19, 2025
🔗 Purchase tickets here
SUP Witches of Sleepy Hollow Festival
October 19
📍 Sleepy Hollow Village Hall, 28 Beekman Avenue, Sleepy Hollow, NY
🗓️ October 17 & 18, 2025
⏰ Block Party: 5 pm | Haunted Hayrides: 7 pm
🎟️ Tickets: Tickets required for the Hayride, sold online only, timed entry. The Block party is FREE Buy Here
Sleepy Hollow Haunted Hayride & Block Party
October 17 & 18
The Sleepy Hollow Haunted Hayride is one of the most popular Halloween events in the Hudson Valley - and it’s happening Friday, October 17, and Saturday, October 18, 2025. Climb aboard for a hair-raising ride through the streets of Sleepy Hollow and into the rolling hills near Sleepy Hollow Cemetery, where spooky surprises await. Tickets are online only with timed entry and always sell out quickly, so mark your calendar for the on-sale date: September 5.
Before your ride, Beekman Avenue shuts down for a lively Sleepy Hollow Block Party starting at 5 pm. This free Halloween festival features live music, food and drink vendors, family activities, and plenty of local energy. The hayrides kick off at 7 pm each night, making it easy to enjoy the block party before or after your ride.
⚡ The Horseman’s Shop will have a table at the Block Party both nights! Stop by to shop Sleepy Hollow souvenirs, Headless Horseman merch, and seasonal favorites.
Tarrytown Halloween Parade
October 25
📍 Parade starts at Patriots Park, Tarrytown, NY
🗓️ Saturday, October 25, 2025 - 5 pm
🚇 Take the train or bus!
The 23rd Annual Tarrytown Halloween Parade is happening on Saturday, October 25, 2025, at 5 pm - one of the biggest spooky season events in the area. The parade kicks off at Patriots Park and makes its way down Broadway to Main Street, where the after-party takes over.
Expect floats, costumes, performers, DJs, live music, outdoor dining, and plenty of Halloween spirit from start to finish. It’s a can’t-miss tradition for Tarrytown and Sleepy Hollow every October.
This is one of the busiest days in Sleepy Hollow so please take the train or bus in! Park in one of the neighboring rivertowns and then take a quick and easy train ride into Tarrytown and walk over to the parade.
Local tip: Head to Main Street early if you want a prime spot for the after-party - the music and crowds build fast once the parade rolls in.