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The Peekskill Weekender

Our top picks for things to do in Peekskill every weekend!

Peekskill comes to life every weekend with great live music, food, art openings, comedy shows, cultural events, dance parties, and more.

We sift through the fun and pick our favorites each week for our Peekskill Weekender series on Instagram. We’re replicating the magic here, with a few extra picks as well.

And for everything to do this weekend and beyond, visit our Event Directory.

Please check with event organizers before heading out!


Flyer for The Irish Comedy Tour featuring 4 Irish comedians posing.
Fri
Mar, 1
8:00 pm
Paramount Hudson Valley Theater
1008 Brown St, Peekskill, NY 10566

The Irish Comedy Tour

Prepare to embark on an uproarious journey with the Irish Comedy Tour, where the infectious party spirit of a Dublin pub collides head-on with a raucous gang of hilariously mischievous merrymakers. This high-octane ensemble, a merry mix of comedians and musicians with roots tracing back to the Emerald Isle, is set to take your funny […] ...

DJ Joey Mercedes on the wheels of steel.
Fri
Mar, 1
9:00 pm
140 Kitchen
911 South Street, Peekskill, NY

DJ Joey Mercedes

Dj Joey Mercedes Rockin the wheels of steel this Friday 9pm 🎶🍸🍹 ...

Maple syrup cook John Neering poses in the Sugar Shack at Depew Park
Sat
Mar, 2
9:00 am - 10:30 am
Depew Park
1 Robin Dr, Peekskill, NY 10566

Maple Sugaring Workshop

Head to the Sugar Shack in Depew Park and learn how maple syrup is made! Participants will learn the step-by-step process of how tree sap becomes maple syrup. Learn how and why sap flows, and how it can become a gallon of maple syrup. Participants will be encouraged to engage in this hands-on presentation. Please […] ...

Flier for Peekskill Clean Routine
Sat
Mar, 2
10:00 am
Charles Point Park
1 John Walsh Blvd, Peekskill, NY 10566

Charles Point Park and Walkway Cleanup

The PeekskillCleanRoutine Team has updated the cleaning project scheduled for Saturday, March 2nd, weather permitting. At 10am, for approximately two hours, we will have a cleanup at Charles Point Park, next to the Holiday Inn Express. This cleanup is for anyone and everyone and is both kid-friendly and pet-friendly. We will clean the park itself […] ...

Sat
Mar, 2
9:00 pm
Gleason’s
23 South Division Street, Peekskill, NY

The Bluechips

The Bluechips are a Rock n’ Roll power trio from New York’s Hudson Valley. As childhood friends, Jake Albi (drums/vocals), Tom Davis (bass), and Paul Beladino (guitar/vocals) spent their first 10 years collaborating through various musical projects before establishing the band 2018. The group’s ethos combines their classic influences with catchy choruses and a modern cognizance, setting them apart from their current rock contemporaries. Since its inception, the band has […] ...

Fred Gillen Jr. on stage with guitar.
Sun
Mar, 3
3:00 pm - 5:00 pm
BeanRunner Cafe
201 South Division Street, Peekskill, NY 10566

Fred Gillen Jr.

Peekskill native, NYFA (New York Foundation For The Arts) grant recipient Fred Gillen Jr has released nine full-length albums, to great critical acclaim, and has toured all over the U.S. and Europe. His songs have been featured on ABC’s “All My Children,” NPR’s “Car Talk,” CMJ’s New Music Marathon Sampler, and in 2012 his version […] ...

Sun
Mar, 3
5:30 pm - 8:00 pm
Ruben's Mexican Cafe
12 N Division Street, Peekskill, NY

Westchester Swing Band

Greg Westhoff and the Westchester Swing Band play the great music of Swing Era and beyond. ...

Flier for Peekskill's St. Patrick's Day Grand Marshal's Kickoff Tour
Fri
Mar, 8
5:15 pm - 10:30 pm
Downtown Peekskill

Grand Marshal’s Kickoff Tour 2024

Celebrate St. Patrick’s Day with the ultimate Peekskill pub crawl! Follow pipe major Joe Brady to nine pub locations throughout Peekskill to celebrate Peekskill’s 33rd St. Patrick’s Day Parade Grand Marshal George Pataki. See you there! ...

A bag piper leads the Peekskill St. Patrick's Day Parade
Sat
Mar, 9
3:00 pm
Downtown Peekskill

Peekskill St. Patrick’s Day Parade

Celebrate Irish pride at Peekskill’s 35th Annual St. Patrick’s Day Parade. The parade steps off near Assumption Church, makes its way down Union Avenue, then right on South Street, left on Division Street, right on Main Street and right on James Street. The reviewing stand is on the corner of James and Park Streets. IRISH […] ...

Flier for After Parade Party at The Elks Lodge
Sat
Mar, 9
4:00 pm
Peekskill Elks Lodge
1038 Brown St, Peekskill, NY

After Parade Party

Head to the Peekskill Elks Lodge after the Peekskill St. Patrick’s Day Parade to enjoy some music and fun. Featuring Phineas & The Lonely Leaves. Come get your Irish on! ...

Flier for House of Waters at South Street Jazz
Sun
Mar, 24
7:00 pm
The Artist Spot
925 South St, Peekskill, New York 10566

South Street Jazz: House of Waters

Grammy Nominated band, House of Waters will be performing at a pop up jazz club in Peekskill NY! South Street Jazz is an intimate listening room vibe similar to iconic NYC clubs such as Smalls, Mezzrow & the Village Vanguard located at the Artist Spot in Downtown Peekskill. ...

Flier for Johnathan Blake at South Street Jazz
Sun
Apr, 21
7:00 pm
The Artist Spot
925 South St, Peekskill, New York 10566

South Street Jazz: Johnathan Blake

Heralded by NPR Music as “the ultimate modernist,” Johnathan Blake will be bringing his music to a pop up jazz club in Peekskill NY. South Street Jazz is an intimate listening room vibe similar to iconic NYC clubs such as Smalls, Mezzrow & the Village Vanguard located at the Artist Spot in Downtown Peekskill. ...

Flier for Adam O'Farrill's Stranger Days at South Street Jazz
Sun
May, 19
7:00 pm
The Artist Spot
925 South St, Peekskill, New York 10566

South Street Jazz: Adam O’Farrill’s Stranger Days

“Among the leading trumpeters in jazz- and perhaps the music’s next major improviser.” – The New York Times South Street Jazz is an intimate listening room vibe similar to iconic NYC clubs such as Smalls, Mezzrow & the Village Vanguard located at the Artist Spot in Downtown Peekskill. ...

No event found!