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The Peekskill Weekender

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

Colores De Mi Tierra Art Exhibit Flyer
Sat
May, 18
2:00 pm - 5:00 pm
Sun River Health
1037 Main Street, Peekskill, NY

Colores De Mi Tierra

The SunRiver Health Jeannette J. Phillips Community Health Center, located at 1037Main Street in downtown Peekskill, will host an opening reception for theirlatest art exhibition featuring the work of Oaxacan artist Eduardo GuzmanValverde in the health center’s Atrium on Saturday, May 18 from 2pm until 5pm. Thereception will also feature performances from El Grupo Folclórico de […] ...

Flier for Dumb Phone Dance Party at The Central
Sat
May, 18
9:00 pm
The Central
300 Railroad Avenue, Peekskill, NY 10566

Dumb Phone Dance Party

The Dumb Phone Dance Party is hosted by Jeremy Larson who will be spinning vinyl with DJ Joey Mercedes — old and new, funk, boogie, and disco heaters! ...

Black and white promotional portraits of the members of What's In The Box NY
Sat
May, 18
9:00 pm
Gleason’s
23 South Division Street, Peekskill, NY

What’s In The Box

Based in Westchester NY, ‘What’s In The Box’ brings the raw energy and authentic spirit of the 90s grunge and alternative scene to life. Formed in early October 2023, our five-piece ensemble is fueled by a shared passion for the defining sounds of the era. Frontman Pete Repole’s angelic vocals, combined with the dynamic guitar […] ...

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 Old Peekskill in Photographs at Lincoln Depot Museum
Sun
May, 19
1:00 pm - 4:00 pm
Lincoln Depot Museum
10 South Water Street, Peekskill, NY 10566

Collectors Corner: Old Peekskill PhotographsDaily

Collectors Corner is when a local collector and their collection are highlighted for a weekend in the museum. The owner of the collection is on hand to describe the artifacts and answer any questions for the visitors. This program is included as part of admission to the museum. ...

Flier for Lyn Slater & The Exurbanist at Newburgh Brewing
Sun
May, 19
2:30 pm - 4:00 pm
Newburgh Brewing Co.
88 Colden Hill Road, Newburgh, NY 12550

The Accidental Icon in Conversation

Catch us in conversation #Peekskill‘s own @iconaccidental at @newburghbrewing this Sunday, May 19 from 2:30-4. We’ll be chatting about her new book “How To Be Old: Lessons in Living Boldly from the Accidental Icon“, discussing cross-generational friendships, life as exurbanists, and more! The event is free and should serve as a fun #PeekskillGetaway for those looking for a little road trip up […] ...

Promotion photo of Laurie Berkner with an acoustic guitar
Sun
May, 19
3:00 pm
Paramount Hudson Valley Theater
1008 Brown St, Peekskill, NY 10566

Laurie Berkner

Give your child an unforgettable experience that will inspire a lifelong love of music and create lasting memories with the whole F-A-M-I-L-Y! Laurie Berkner Solo concerts are a special way to give your child a chance to experience music they love, performed live. The shows are highly-acclaimed, and we welcome fans of all ages and […] ...

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. ...

Flier for The Bluechips at Gleason's
Sat
May, 25
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 […] ...

Promotional portrait of magician Ran D Shine
Sun
May, 26
4:00 pm
The Artist Spot
925 South St, Peekskill, New York 10566

Magician Ran’D Shine – Evidence of Things Unseen

Magician Ran’D Shine presents his acclaimed show “Evidence of Things Unseen” at The Artist Spot in Peekskill. Starring Ran’D Shine and directed by Hiawatha Johnson Jr, this intimate theatrical production is immersive, surprising, and unexpected. In “Evidence of Things Unseen” both classic and modern magic effects create miracles before your eyes, while constructing metaphors in […] ...

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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!