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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!


Flier for Bicycle Sundays in Depew Park
Sun
May, 19
7:00 am - 12:00 pm
Depew Park
1 Robin Dr, Peekskill, NY 10566

Bicycle SundaysWeekly

Enjoy a ride with family and friends on the roadways in Depew Park on Sunday mornings. Roadways will be blocked off to motorized vehicles. Parking is available in pool parking lot. Cars must enter from Union Ave. For More Information Call The Recreation Office at 914-734-7275 ...

Drone shot of Westchester Cars & Coffee on Water Street in Peekskill
Sun
May, 19
8:00 am - 10:00 am
Water Street Municipal Parking Lot
24 S Water St, Peekskill, NY, 10566

Westchester Cars and CoffeeWeekly

Check out local cars of all kinds right in the heart of the Historic Peekskill Waterfront. Happens at the Water Street parking lot right next to Homestyle Desserts. ...

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!