Events in Sleepy Hollow
Can’t Make It to Our Booth? Shop Spooky Season Favorites
Celebrate fall in the home of the Headless Horseman with our Spooky Season in Sleepy Hollow Sweatshirt. Inspired by the sights, traditions, and Halloween spirit that make our hometown of Sleepy Hollow so special, this cozy crewneck brings together some of our favorite local icons in one vintage-inspired design.
From the Headless Horseman and Old Dutch Church to the Tarrytown Halloween Parade, Haunted Hayride, local landmarks, and other spooky details, there’s plenty to discover throughout the artwork. It’s the perfect sweatshirt for crisp fall days, October adventures, or anyone who wishes spooky season in Sleepy Hollow lasted all year.
Details:
Sleepy Hollow-inspired design: Features a collection of local landmarks, Halloween traditions, and spooky icons inspired by Sleepy Hollow, New York.
Please note, the vibrancy of the colors may appear washed depending on the color of the sweatshirt.
Cozy unisex fit: Classic crewneck sweatshirt with a comfortable, relaxed fit for easy everyday wear.
50% cotton / 50% polyester: Soft, warm, and durable for chilly fall days and cool nights.
Medium-heavy fabric: Cozy enough for pumpkin season without feeling overly bulky.
Classic crewneck: Finished with a ribbed knit collar, cuffs, and waistband.
Sizing: Runs true to size. For a more oversized, cozy fit, we recommend sizing up.
Perfect for fall in Sleepy Hollow: Wear it while exploring Sleepy Hollow, visiting local spooky events, or simply bringing a little spooky-season spirit home with you.
Whether you’re a Sleepy Hollow local, planning an October visit, or just love all things Halloween, the Spooky Season in Sleepy Hollow Sweatshirt is made for the best time of year.
Step into the mystique of Sleepy Hollow with The Headless Horseman Vintage Sweatshirt! This unisex heavy blend crewneck is a tribute to one of America’s most haunting legends. Designed with a classic vintage-inspired look, this sweatshirt prominently features the Headless Horseman, letting you carry a piece of Sleepy Hollow's eerie folklore wherever you go.
Why You’ll Love It:
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Legendary Design: Inspired by the rich history of Sleepy Hollow, this sweatshirt showcases the iconic Headless Horseman in a vintage style, perfect for fans of the eerie tale. Whether you're strolling near the Old Dutch Church or the legendary Headless Horseman Bridge, this sweatshirt lets you embody the spirit of Sleepy Hollow’s spookiest landmarks.
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Cozy & Durable: Made from a balanced blend of 50% cotton and 50% polyester, this medium-heavy fabric (8.0 oz/yd²) sweatshirt is built for warmth and comfort. The ribbed knit collar and double-needle stitching on the shoulders, armholes, and cuffs ensure it holds its shape and withstands the test of time—so it’s ready for all your adventures in the crisp fall air.
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Classic Fit for All: With a timeless, unisex fit and clean-cut crew neckline, this sweatshirt provides a relaxed yet stylish look. Perfect for layering up as you explore haunted sites or enjoy cozy nights by the fire. True to size; consider sizing up for a more oversized, laid-back vibe.
Whether you're a Sleepy Hollow local, a visitor, or simply a fan of Washington Irving's legendary tale, The Headless Horseman Vintage Sweatshirt is the ultimate way to showcase your love for one of America’s spookiest destinations. Perfect for wandering the historic streets of Sleepy Hollow or just adding a touch of haunting charm to your everyday style, this sweatshirt will keep you warm and stylish all season long.
Introducing our Sleepy Hollow Headless Horseman Hat - a timeless tribute to the village made famous by Washington Irving's legendary tale. Featuring embroidered "Sleepy Hollow, New York" lettering and the iconic Headless Horseman silhouette, this vintage-washed cap combines local history with everyday style.
Whether you're exploring Sleepy Hollow Cemetery, visiting the historic Old Dutch Church, browsing the Sleepy Hollow Street Fair, or simply showing off your love for The Legend of Sleepy Hollow, this comfortable hat is the perfect companion for every season.
Designed with a relaxed fit and a vintage washed finish, it has the broken-in look and feel of an old favorite from the very first wear. Simple, comfortable, and proudly local, it's a must-have for Sleepy Hollow residents, former locals, history enthusiasts, and visitors looking for authentic Sleepy Hollow souvenirs and unique Headless Horseman gifts.
Details:
• Embroidered Sleepy Hollow, New York design
• Features the iconic Headless Horseman silhouette
• Vintage washed finish for a worn-in look
• Relaxed, unstructured fit
• Adjustable strap for a customizable fit
• Lightweight and comfortable for everyday wear
• Great for locals, visitors, and fans of The Legend of Sleepy Hollow
A classic Sleepy Hollow souvenir inspired by the village's legendary history, iconic landmarks, and the enduring tale of the Headless Horseman.
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
🔗 Learn More
Tarrytown Street Fair
September 26
Prost! Sleepy Hollow’s 14th Annual Oktoberfest is happening on Saturday, September 26, 2026, 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 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!
⚡ 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
🗓️ Saturday, 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
⏰ 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
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 currently SOLD OUT
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. This event is open to ALL whether or not you are going to the Haunted Hayride.
⚡ 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, 2026, 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.
The Sleepy Hollow Street Fair is back on Sunday, November 8, 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.
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
🔗 Learn More