Also check out: Entertaining Things to do in Tarrytown

September

Sleepy Hollow Street Fair

Sep 27 (Sun) 10am-5pm

Beekman Ave, Sleepy Hollow

Step into the heart of the legend at the Sleepy Hollow Street Fair, the ultimate destination for anyone who lives for the spooky season! Set against the backdrop of the world’s most famous haunted village, this high-energy festival transforms Beekman Avenue into a massive outdoor celebration of all things Halloween and autumn. From artisanal vendors selling eerie treasures to live music and mouth-watering local food trucks, the energy is absolutely electric.
Whether you’re hunting for unique gothic crafts, soaking up the mysterious local atmosphere, or just exploring the legendary streets where the Headless Horseman rides, this fair is a must-visit for every Halloween lover. Don't miss out on the most spirited event in New York—it’s the perfect way to kick off your spooky season adventures in Sleepy Hollow!

Film Series: Gregg Allman

The Music of My Soul

Sep 25 (Fri) 8pm

Tarrytown Music Hall

Featuring a post film conversation with Michael Lehman, Gregg’s longtime manager and the film’s producer and Thomas Staudter, a Hudson Valley writer whose work has appeared in The New York Times, Reader’s Digest, DownBeat and elsewhere.
The Music Hall is excited to announce an exclusive screening of Gregg Allman: The Music of My Soul, the highly acclaimed full-length feature documentary exploring the life and work of the late, great Gregg Allman.  $2 from tickets sold for all screenings of Gregg Allman: The Music of My Soul will benefit the Gregg Allman Scholarship Funds. Due to the nature of the film, Michael Lehman, Lead producer and longtime friend and client, felt Allman Brothers Band fans and lovers of music will want to see this film on the big screen with a professional PA system in venues that, in many cases, had presented live performances from Allman, Dickey Betts, Jaimoe, or the Allman Brothers Band themselves.

An Evening with Josh Ritter

Sep 26 (Sat) 8pm

Tarrytown Music Hall

Josh Ritter is a renowned singer, songwriter, musician, artist and best-selling author. One of today’s most thoughtful and prolific voices, he has released eleven studio albums including 2019’s widely acclaimed ‘Fever Breaks’ of which NPR Music praised, “He remains a hydrant of ideas while embodying an endless capacity for empathy and indignation, often within a single song.”
His twelfth studio album ‘I Believe in You, My Honeydew’ is out now. Two-plus decades into his celebrated career, Ritter has written music that has transcended generations including luminaries such as Bob Dylan, Joan Baez, and Bob Weir covering his songs.
The Book of Gold Thrown Open tour is meant to encompass the whole of Ritter’s career, versus focusing on any one studio album.

Rivertown Dance Academy Fundraiser

Sep 27 (Sun) 5pm-8:30pm

Silver Pro Music, Hartsdale

Celebrate, dance, and support RDA’s financial aid program at Silver Fest! 

Held at Silver Pro Music, a glitsy recording studio and event venue in Hartsdale, the evening includes a professional performance, a cocktail hour and fine spirit tasting, mystic readings, prizes and a tasting menu of Peruvian Latin fusion cuisine. The night wraps up with a DJ’d dance party below the disco lights. 

This year, for the first time, kids party, too! A pizza party at Clubhouse Central, a private play space located next door to the main event, offers parents an affordable childcare option. 

Join us! And be a part of the magic. 
Get your tickets now, because prices go up September 21. RivertownDanceAcademy.org/silverfest

October

Sleepy Hollow Music Festival

Oct 3 (Sat) Time 11am-8pm

Kingsland Point Park, Sleepy Hollow

Get ready to rock the valley at the 3rd Annual Sleepy Hollow Music Festival where a massive dose of 90s nostalgia meets the edge of the Hudson River. This year’s stacked lineup features multi-platinum alternative rock headliners Everclear, Fastball, and The Smithereens performing alongside a fantastic array of local food trucks, craft beer gardens, and artisanal craft vendors. It is the ultimate family-friendly environment to kick off the village's world-famous Halloween season with non-stop live performances spanning multiple stages. Extend your festival weekend by exploring the charming, historic streets of neighboring Sleepy Hollow and Tarrytown. Take a short stroll from the music to uncover the legends of Washington Irving at the Sleepy Hollow Cemetery, or head down to Tarrytown's bustling Main Street for boutique shopping and outdoor dining. You can wrap up your trip by snapping a photo of the legendary Tarrytown Music Hall, ensuring a perfect blend of historic river town charm and unforgettable rock-and-roll energy.

Tarrytown Halloween Parade

& Block Party

Oct 24 (Sat)

Pre-activities 12pm

Parade 5pm

Block Party begins after parade

Broadway & Main St, Tarrytown

Experience the legendary Tarrytown Halloween Parade on Saturday, October 24, 2026, a high-energy spectacle that is the ultimate spooky season tradition in the Hudson Valley! The excitement is electric as massive, intricately designed floats roll by featuring next-level live performances, while both the parade-goers and the crowd show up in "next-level" crazy costumes for the best people-watching in New York.
Make a full day of it by arriving early to explore the historic downtown; it's the perfect time to visit the local boutiques to snag special spooky offerings and limited-edition Halloween treats you won't find anywhere else. The parade officially kicks off at 5:00 PM, and the adrenaline stays high as a massive Block Party begins right afterward! Whether you are marvelling at the professional choreography on the moving stages or dancing in the streets at the after-party, the Tarrytown Halloween Parade is an absolute must-visit for a wild and unforgettable night.

November

 

December

6th Annual Tarrytown Winter Stroll

Dec 12 (Sat) 12-5pm

Tarrytown & Sleepy Hollow 

Experience the magic of the season at the Tarrytown Winter Stroll, the ultimate holiday event that transforms our historic downtown into a glowing winter wonderland! This high-energy evening is a must-visit for families and festive shoppers, featuring live carolers, dazzling window displays, and extended hours at our unique local boutiques. Whether you’re sipping on hot chocolate, enjoying special holiday treats from our world-class restaurants, or soaking up the electric community atmosphere, the vibes are pure holiday joy. 
Don't miss your chance to explore the heart of Tarrytown during this vibrant seasonal festival—it’s the perfect way to experience the village’s cozy charm and spirited energy under the twinkling lights. It is truly the most wonderful time of the year in the Hudson Valley!

January 2027