Events in Sleepy Hollow
June 7
The Tarrytown Street Fair returns to Main Street on Sunday, June 7, 2026, from 10 am to 5 pm and it is one of the best free summer days in Westchester! Every June, Main Street shuts down and transforms into a lively open-air celebration with tons of local vendors, food, live music, and a true small-town block party energy. Whether you're a longtime local or just visiting for the day, it's a perfect excuse to wander, grab a bite, support local small businesses and see what's new in one of the most charming villages on the Hudson.
⚡ The Horseman's Shop will be there too! Stop by our booth for Sleepy Hollow and Tarrytown souvenirs - perfect for summer gifts or a little something to remember the day.
📍Main Street , Tarrytown, NY
🗓️ Sunday, June 7, 2026
🕰️ 10am - 5pm
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Tarrytown Street Fair
September 20
Sleepy Hollow Street Fair
The Sleepy Hollow Street Fair is back on Sunday, September 20, 2026, from 10 am to 5 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.
⚡ The Horseman’s Shop will be there too! Stop by our booth for Sleepy Hollow souvenirs and spooky-season merch!
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 14th Annual Oktoberfest is happening on Saturday, September, 2026, from 1–5 pm at Kingsland PointPark. 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 Saturday, October 10, 2026, from 12–5 pm (rain date October 11). 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!
NOT CONFIRMED, TBD⚡ 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 10, 2026 - 12–5 pm
🌧️ Rain Date: Sunday, October 11, 2026
🔗 Purchase tickets here
SUP Witches of Sleepy Hollow Festival
October 10
📍 Sleepy Hollow Village Hall, 28 Beekman Avenue, Sleepy Hollow, NY
🗓️ October 16 & 17, 2026 - TBD
⏰ 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 16 & 17
TBD - The Sleepy Hollow Haunted Hayride is one of the most popular Halloween events in the Hudson Valley - and it’s happening Friday, October 16, and Saturday, October 17, 2026. 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: TBD
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.
NOT CONFIRMED, TBD⚡ 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.
Tarrytown Halloween Parade
October 24
📍 Parade starts at Patriots Park, Tarrytown, NY
🗓️ Saturday, October 24, 2026 - 5 pm
🚇 Take the train or bus!
The 24th Annual Tarrytown Halloween Parade is happening on Saturday, October 24, 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.
July 18
The Sleepy Hollow Mermaid Festival splashes into Kingsland Point Park on Saturday, July 18, 2026 (rain date Sunday, July 19) - and it's one of the most magical events of the summer. This community celebration brings together mermaids, artists, performers, and Hudson River lovers for a one-of-a-kind day on the riverwalk. Highlights include a costume parade on both land and water, live music, art-making, a costume contest, food trucks, and local vendors and makers. It's equal parts whimsical and community-rooted - a true Sleepy Hollow original.
The festival is also a celebration of the Hudson River itself, with Riverkeeper as a partner and a mission to encourage river access and education. All are welcome, and it's completely free!
📍Kingsland Point Park , Sleepy Hollow, NY
🗓️ Saturday, July 18, 2026
🕰️ TBD
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