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Peek-a-boo! Things to do in Peekskill this Halloween

There’s no shortage of fun, spooky events and other things to do leading up to Halloween here in Peekskill, NY. We’ve compiled a list of some of our picks for things to do in and around Peekskill whether you’re into tricks or treats.

This is just a sampling of what’s going on, visit our microsite 🎃 🎃 for a calendar of all the Halloween events in town.

1. Run for “Boos” with the Run PB team’s costume run

The folks over at Run PB are pros at turning exercise into a party and Halloween is no exception. So this Wednesday, October 25th, throw on your favorite costume, lace up your running shoes, and head over to Peekskill Brewery at 6 p.m. for a fun walk/run with the crew followed by drinks at the brewery starting at 7 p.m.

2. Bring the kiddos to Peekskill’s many trunk or treats

Flier for Nardone Funeral Home Trunk Or Treat

Join the Peekskill Fire Department at their 2nd Annual Trunk or Treat on Friday, October 27th from 6 – 8 p.m. The event takes place at the Peekskill Central Fire House and families are encouraged to wear their costumes and enjoy all the treats, music, and activities. The Peekskill PTO presents a Trunk Or Treat on Saturday, October 28th from 10 a.m. to 1:00 p.m. at Peekskill Middle School Saturday Academy. Then head over to Nardone Funeral Home for their 4th Annual Trunk Or Treat from 2:00 p.m. – 5:00 p.m.

3. Choose a decade at the 70s vs 80s dance party at Sunset House

The Halloween edition of EVRBDY @ Sunset House comes with a theme: battle of the decades, 70s vs 80s. DJ’s @joey_mercedes88 + @ronandkerr are serving up some deep cuts from decades past to help you find the best that moves your feet! Costumes are encouraged, so choose your decade wisely. See you at Sunset House on Friday, October 27th at 8 p.m.

4. Visit a very pumpkin-y Peekskill Farmers Market

The weekly Peekskill Farmers Market will feature a seasonal twist with a Guess the Weight of the Giant Pumpkin Contest along with a Halloween Pumpkin Design workshop on Division Street for kids up to 6th grade. The Farmers Market is open from 8 a.m. to 2 p.m. on Saturday, October 28th and the Pumpkin Design workshop goes from 11 a.m. to 1 p.m.

5. Crawl like a Zombie to Downtown Peekskill bars

Flier for the Peekskill Halloween Zombie Crawl

The undead awaken at 6 p.m. on Saturday, October 28th in Downtown Peekskill but instead of brains they’re on the hunt for BOOOZE! Luckily there’s no shortage of that in Peekskill, so join the fun and crawl your way to Gleason’s, Slàinte, Rueben’s, Peekskill Smokehouse, Whiskey River, and ultimately Birdsall House. Each venue will be hosting its own Halloween celebration with live music, costume contests, and more.

6. Watch cult classic The Rocky Horror Picture Show at the historic Paramount Hudson Valley Theater

Do the time warp! Come in costume and join The Apoca-Lips Cast as they shadow the 1975 cult classic The Rocky Horror Picture Show. The fun starts at 9 p.m. on Saturday, October 28th.

7. Get a burger and fries at Benny’s Brown Bag as they transform into Bob’s Burgers for Halloween

Benny's Brown Bag is rebranded as Benny's Burgers as they dress up as Bob's Burgers for Halloween.

Benny’s Brown Bag — Peekskill’s acclaimed new sandwich shop — will be partnering with the incredible @marbledmeatshop and transforming Benny’s into Bob’s Burgers! Staff will be dressed as their favorite characters and Benny’s will be OPEN from 11:00a – 2:00p ONLY serving a special 1/4 lbs burger and fries combo for $10.31 (very limited quantities).

8. Check out Peekskill’s most impressive Halloween display on Riverview Avenue

Henry Seger's elaborate Halloween Pirate Ship display in his front yard featuring a skeleton mutiny on a life size pirate ship

Head up to the corner of Riverview and Longview Avenue in the Mortage Hill neighborhood of Peekskill to witness Henry Seger’s incredible haunted pirate ship Halloween display in his front yard. It has to be seen to be believed, but this skeleton pirate mutiny has become a yearly tradition here in town. The Peekskill Herald has the backstory.