Also check out: Entertaining Things to do in Tarrytown

June

Comedy: Joe Avati

June 12 (Fri) 7pm

Tarrytown Music Hall

Internationally renowned for his inimitable style Avati, who is Australian born with an Italian heritage, is one of the most significant and pivotal comedians of his generation who, undoubtedly, is directly responsible for the ethnic comedy circuit around the world today. For the past 30 years Joe Avati’s routines about growing up with a culturally diverse background have gained him a cult following around the globe. Avati has also become the master of treading the very fine line of saying whatever everyone seems to think but no one dares to say whilst not resorting to the use of profanities or vulgar shock tactic routines and in doing so allowing audiences of all ages to attend his shows. He has a razor sharp wit and his observations are not only deadly accurate but extremely relatable to his growing international audiences. Joe Avati is, without doubt, one of the world’s most loved and successful comedians of his generation.

Shakey Graves - Fondness, Etc. Tour

June 14 (Sun) 7pm

Tarrytown Music Hall

Across his career, Shakey Graves—a.k.a. the performance moniker of Austin, Texas- born Alejandro Rose-Garcia—has intentionally created thrilling musical adventures tailored to each fan: burning CDs and putting them in personalized decorated bags; building intricate scavenger hunts that send fans in search of unique tapes; and Bandcamp-exclusive releases. "The fans and musicians that really resonate with me—and the inexplicable ways that I find things that I like—are usually entirely through randomness and chaos and accident," Rose-Garcia says. "I've always been on this quest to make people feel like my own music is a choose your own adventure."

Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb

June 19 (Fri) 7pm

Tarrytown Music Hall

Classic films in a classic venue.
A mentally unstable American general orders a hydrogen bomb attack on the Soviet Union, triggering a path to global nuclear holocaust that a war room full of politicians and generals frantically tries to stop.

Runtime: 95 Minutes. Directed by Stanley Kubrick. Starring Peter Sellers. Rated PG

Aziz Ansari: Hypothetical Tour

June 24 (Wed) 7pm

Tarrytown Music Hall

Aziz Ansari is an award-winning actor, director, writer and comedian. He co-created, writes, directs, and stars in the Netflix original series MASTER OF NONE for which he has won two Emmy’s for Outstanding Comedy Writing as well as Emmy and DGA Award nominations for his directing. He recently released the film GOOD FORTUNE which he wrote, directed, and costars with Keanu Reeves and Seth Rogen. He is also known for co-starring in NBC’s PARKS AND RECREATION and for being one of the few headlining comedians ever to sell out Madison Square Garden. In 2019, he released his 5th standup for Netflix entitled RIGHT NOW directed by Spike Jonze to critical acclaim and a Grammy nomination. His latest special NIGHTCLUB COMEDIAN is now streaming on Netflix.

Patton Oswalt: Effervescent

June 25 (Thurs) 8pm

Tarrytown Music Hall

Patton Oswalt continues to leave his distinctive imprint across all areas of entertainment, from his award-winning comedy specials to his many guest roles on television. His most recent comedy special We All Scream (which also marked his directorial debut) launched on Netflix last September and Oswalt was recently nominated for a Grammy for his comedy album. Last year, he starred in the Magnolia Pictures comedy I Love My Dad, winner of the Grand Jury and Audience awards at the 2022 SXSW Film Festival.
Oswalt was nominated for a Critics Choice Award for his performance in Jason Reitman’s film Young Adult, starring opposite Charlize Theron. In 2009, he also received critical acclaim for his performance in Robert Siegel’s Big Fan; the film was nominated for an Independent Spirit Award and Oswalt earned a Gotham Award nomination for his performance.

Manhattan Comedy Night

June 27 (Sat) 8pm

Tarrytown Music Hall

Manhattan Comedy Night returns to the Tarrytown Music Hall on Saturday, June 27, 2026, for a 90-minute showcase of top-tier stand-up. The lineup features seasoned NYC comedy club veterans.

The night's roster features the following comedians: Gus Tate: A regular at top NYC clubs known for his clever, relatable observational humor covering everyday life, relationships, and the quirks of parenting. Matt Koff: A sharp, dry stand-up and Emmy-winning writer widely recognized for his hilarious, deadpan stints on The Daily Show. Mike Yard: A hard-hitting, energetic comedian best known as a regular contributor on The Nightly Show with Larry Wilmore and a favorite at the Comedy Cellar. Bonnie McFarlane: A veteran headliner, podcaster (My Wife Hates Me), and author known for her incredibly sharp, edgy, and brutally honest comedic style. Harrison Greenbaum: An award-winning NYC favorite known for blending rapid-fire stand-up with magic, illusions, and high-energy crowd work.

Tarrytown Community

Block Party

June 28 (Sun) 12-4pm

Tarrytown Main Street

Get ready to take over the streets because the Tarrytown Community Block Party is officially in the works! We’re shutting down Main Street to cars and opening it up for a massive pedestrian celebration filled with non-stop music, incredible festivities, and pure neighborhood vibes. Imagine wandering the heart of town with total freedom, dancing in the street, and soaking up the best of our local scene with your favorite people.
The date and time are still under wraps, so stay tuned—this is going to be the ultimate community hang you won't want to miss!

July

Tarrytown

Summer Concert Series

July 2 - Aug 27

(Thursdays) 7-9pm

Pierson Park

Unwind under the stars with the ultimate summer vibe. Grab your favorite people, pack a blanket, and let the music set the perfect backdrop for a memorable night out. Whether you are cheersing with friends or looking for that effortless, romantic date night, this concert series brings the community alive with incredible live tunes, great energy, and unforgettable summer memories.

Independence Day Festivities & Fireworks

July 4 (Sat) All Day

All over Tarrytown

Celebrate Independence Day in the ultimate riverfront style with an unforgettable July 4th in Tarrytown! Spend your day wandering through our sun-drenched historic streets, popping into eclectic shops, and grabbing a festive bite at a local sidewalk cafe. 

Then head over to the riverfront for a massive celebration. The energy kicks off at Pierson Park with a fleet of food trucks, family activities, and a dedicated Kid Zone featuring face painting and games. As the sun sets, enjoy a high-energy live music performance that leads right up to the main event: a spectacular fireworks display over the Hudson River at 9:00 PM. Pro Tip: Skip the traffic and parking stress by taking the Metro-North train—it drops you off right in the heart of the action!

Sleepy Hollow Mermaid Festival

July 18 (Sat) 1-5pm

Kingsland Point Park

Trade your sneakers for a tail watch as Mermaids plunge into the Hudson at the Sleepy Hollow Mermaid Festival! This out-of-towner’s dream boasts a vibrant land-and-water parade, giant sea-creature puppets, and live samba bands. Celebrate the river with food trucks, pop-up markets, and a lively beach party—you absolutely cannot miss this magical splash!

Tri the Park Tarrytown Youth Triathlon

July 19 (Sun) 8am

Pierson Park

Tarrytown’s first Youth Triathlon will be coming to Pierson Park on July 19th! Registration will open April 1st at 10am.

September

Pet Parade

Sep 12 (Sat)

Tarrytown - Pierson Park

Get ready for the most adorable takeover in the Hudson Valley at the Tarrytown Pet Parade! This high-energy community event is a must-visit for animal lovers, bringing together hundreds of local pets and their owners for a colorful, costume-filled march through our historic streets. From prize-winning outfits to pawsome local vendors and family-friendly activities, the atmosphere is pure joy and non-stop fun.
Whether you're showing off your own furry friend or just coming to soak up the "pawsitive" vibes, the Tarrytown Pet Parade is the ultimate way to celebrate our four-legged neighbors. It’s a quirky, spirited, and totally essential village tradition that you won’t want to miss!

Sleepy Hollow Street Fair

Sep 20 (Sat) 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!

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

Oct 24 (Sat) Time tba

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!