Also check out: Entertaining Things to do in Tarrytown

July

Jazz at Pierson Park

July 24 (Fri) 6:30-8pm

Pierson Park

Pack up your picnic blankets and make a full day of it in the village before heading down to the waterfront! Before the smooth rhythms begin, spend your afternoon wandering through our historic downtown to enjoy some local shopping at our unique nearby boutiques and specialty stores. Once you've scored your local finds, head to the water's edge for an incredible, recurring sunset series that brings world-class jazz artists right to the grass. With a high-vibe community crowd, plenty of space to relax, and a stunning backdrop of the sun setting over the Hudson, it is the absolute perfect way to elevate your summer nights.

EagleMania

Eagles Tribute Band

July 25 (Sat) 8pm

Tarrytown Music Hall

EagleMania has dedicated themselves to faithfully reproducing the music of The Eagles. Since their inception, EagleMania has been thrilling audiences all over the country with their stunning five part harmony and their uncanny ability to emulate the unmistakable sound of The Eagles. Their show consists of the Eagles’ greatest hits, as well as some of the solo work of Don Henley, Glenn Frey, and Joe Walsh.EagleMania has spent countless hours breaking down everything The Eagles recorded on their albums and faithfully reproducing those unforgettable songs in the most authentic way possible. The audience is given a chance to experience the music the way it was meant to be heard and it’s done live on stage night after night.

Tarrytown

Summer Concert Series

July 30 (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.

Jazz at Pierson Park

July 31 (Fri) 6:30-8pm

Pierson Park

Pack up your picnic blankets and make a full day of it in the village before heading down to the waterfront! Before the smooth rhythms begin, spend your afternoon wandering through our historic downtown to enjoy some local shopping at our unique nearby boutiques and specialty stores. Once you've scored your local finds, head to the water's edge for an incredible, recurring sunset series that brings world-class jazz artists right to the grass. With a high-vibe community crowd, plenty of space to relax, and a stunning backdrop of the sun setting over the Hudson, it is the absolute perfect way to elevate your summer nights.

August

Tarrytown

Summer Concert Series

Aug 6 (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.

Jazz at Pierson Park

Aug 7 (Fri) 6:30-8pm

Pierson Park

Pack up your picnic blankets and make a full day of it in the village before heading down to the waterfront! Before the smooth rhythms begin, spend your afternoon wandering through our historic downtown to enjoy some local shopping at our unique nearby boutiques and specialty stores. Once you've scored your local finds, head to the water's edge for an incredible, recurring sunset series that brings world-class jazz artists right to the grass. With a high-vibe community crowd, plenty of space to relax, and a stunning backdrop of the sun setting over the Hudson, it is the absolute perfect way to elevate your summer nights.

Tarrytown

Raíces y Ritmo

Aug 9 Sunday 3-5pm

Pierson Park

Founded in White Plains, NY in 2019, Grupo Kaukalli was created with a passion for preserving and sharing the beauty of Mexican folklore and traditions through dance. Every performance is a celebration of our raíces—honoring the stories, rhythms, and cultural pride passed down through generations.

Through every step and every skirt, we bring our heritage to life while creating joy, connection, and community. Join us for Raíces y Ritmo as we celebrate culture, music, and tradition together. More than a performance, it is a tribute to who we are and the beauty of sharing our culture with others. Event is free and open to the public.

Tarrytown

Summer Concert Series

Aug 13 (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.

Jazz at Pierson Park

Aug 14 (Fri) 6:30-8pm

Pierson Park

Pack up your picnic blankets and make a full day of it in the village before heading down to the waterfront! Before the smooth rhythms begin, spend your afternoon wandering through our historic downtown to enjoy some local shopping at our unique nearby boutiques and specialty stores. Once you've scored your local finds, head to the water's edge for an incredible, recurring sunset series that brings world-class jazz artists right to the grass. With a high-vibe community crowd, plenty of space to relax, and a stunning backdrop of the sun setting over the Hudson, it is the absolute perfect way to elevate your summer nights.

Tarrytown

Summer Concert Series

Aug 20 (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.

Jazz at Pierson Park

Aug 21 (Fri) 6:30-8pm

Pierson Park

Pack up your picnic blankets and make a full day of it in the village before heading down to the waterfront! Before the smooth rhythms begin, spend your afternoon wandering through our historic downtown to enjoy some local shopping at our unique nearby boutiques and specialty stores. Once you've scored your local finds, head to the water's edge for an incredible, recurring sunset series that brings world-class jazz artists right to the grass. With a high-vibe community crowd, plenty of space to relax, and a stunning backdrop of the sun setting over the Hudson, it is the absolute perfect way to elevate your summer nights.

Tarrytown

Summer Concert Series

Aug 27 (Thursday) 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.

Jazz at Pierson Park

Aug 28 (Fri) 6:30-8pm

Pierson Park

Pack up your picnic blankets and make a full day of it in the village before heading down to the waterfront! Before the smooth rhythms begin, spend your afternoon wandering through our historic downtown to enjoy some local shopping at our unique nearby boutiques and specialty stores. Once you've scored your local finds, head to the water's edge for an incredible, recurring sunset series that brings world-class jazz artists right to the grass. With a high-vibe community crowd, plenty of space to relax, and a stunning backdrop of the sun setting over the Hudson, it is the absolute perfect way to elevate your summer nights.

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!