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!
Lincoln Depot Museum
10 South Water Street, Peekskill, NY 10566Lincoln Kids & Families
Learn the story of 16-year old local patriot Sybil Ludington and her now-famous ride to alert the militia to the approach of British Troops. Come hear the story of the girl, the ride, and the legend it created! The book is Sybil Ludington Discovering the Life of a Revolutionary War Hero with Author and Local […] ...
Gleason’s
23 South Division Street, Peekskill, NYThe David August Sextet
Join us for a special evening of jazz, this Sunday at 6pm! The David August Sextet plays the Gleason’s stage. Featuring: Mindy Sax, Andy Abel, Thierry Arpino, Andrew Beals, Kip Sophos $10/person cover. Cash only. ...
Peekskill Riverfront Green Park
Railroad Ave Peekskill, NY 10566Peekskill Cherry Blossom Festival
Celebrate the beginning of spring, when the 100 cherry trees along the Riverfront Walkway start to bloom. The Rotary Club of Peekskill will hold its Annual Cherry Blossom Festival on Saturday, May 4, 2024 at the Peekskill Riverfront Green. It is our hope that you will be able to join us in celebrating the beginning of spring, […] ...
Peekskill Riverfront Green Park
Railroad Ave Peekskill, NY 10566Cherry Blossom Festival & Plant Sale
Celebrate the beginning of spring, when the 100 cherry trees along the Riverfront Walkway start to bloom. Admission and parking are free with easy access from the Peekskill train station. The Rotary Club of Peekskill will hold its Annual Cherry Blossom Festival on Saturday, May 4, 2024 at the Peekskill Riverfront Green. It is our […] ...
Water Street Municipal Parking Lot
24 S Water St, Peekskill, NY, 10566Westchester 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. ...
Station Square
300 Railroad Ave, Peekskill, NY 10566Mother’s YAY! Market
An outdoor maker’s market to ring in the spring! Join YAY! Markets on Saturday, May 11th for our second annual Peekskill Mother’s YAY! Market at Station Square, right outside the Peekskill Train Station, just an hour from NYC. We’ve got a lineup of 30+ incredible vendors and all-day entertainment for an unforgettable local shopping experience. […] ...
The Artist Spot
925 South St, Peekskill, New York 10566South 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. ...