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The Peekskill Weekender

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

Visit our Event Directory for a list of everything happening in town.

Caribbean Island Sound Band playing outside along the Hudson River
Fri
Oct, 4
7:00 pm - 10:00 pm
Restaurant Row on N. Division
40 North Division Street, Peekskill, NY

Peekskill Summer Series: Caribbean Soul Band

The Caribbean Soul Band, Feel the Island Breeze! šŸŒ“āœØ and immerse yourself in the vibrant sounds of The Caribbean Soul Band. And yes, theyā€™re bringing steel drums! ...

SebastiƔn Natal performs at BeanRunner Cafe in Peekskill, NY
Fri
Oct, 4
7:00 pm - 9:00 pm
BeanRunner Cafe
201 South Division Street, Peekskill, NY 10566

Salsa Night with Sebastian Natal

SebastiĆ”n Natal is an Uruguayan multi-genre, multi-instrumentalist, and music producer. He is proficient in piano, bass, percussion, trumpet, trombone, and vocals, across a variety of genres including salsa, samba, tango, Afro-Peruvian music, Cuban timba, Latin jazz, candombe, Argentine folklore, and Cuban son. SebastiĆ”n’s broad range of talents has afforded him numerous opportunities, touring and performing […] ...

Rose Dance Party at Birdsall House in Peekskill, NY
Fri
Oct, 4
8:00 pm
Birdsall House
970 Main St, Peekskill, NY 10566

RosƩ Dance Party

Ronan and Joey = DJ RosĆ©. They’ll be bringing the beats and the vibes to the Birdsall beer garden. ...

The Doo Wop Project at The Paramount in Peekskill, NY
Fri
Oct, 4
8:00 pm
Paramount Hudson Valley Theater
1008 Brown St, Peekskill, NY 10566

The Doo Wop Project

Step back in time and witness the evolution of Doo Wop like never before with The Doo Wop Project at Paramount Hudson Valley on October 4! Prepare for a journey that transcends decades, from the humble beginnings of harmonizing on street corners to the chart-topping hits dominating the airwaves today. Experience the magic as The […] ...

The 3 B's perform live in Peekskill, NY
Fri
Oct, 4
9:00 pm
Gleasonā€™s
23 South Division Street, Peekskill, NY

The 3 B’s

The 3 B’sĀ are aĀ smokin’ hot blues bandĀ based in Ossining, NY. Classic and contemporary blues covers and originals. Make your reservation now ...

Flier for Peekskill Farmers Market
Sat
Oct, 5
8:00 am - 2:00 pm
Bank Street
Bank Street, Peekskill, NY 10566

Peekskill Farmers MarketWeekly

The Annual Peekskill Farmers Market gets underway on Bank Street in June and runs every Saturday, rain or shine, through the Saturday before Thanksgiving, offering fresh seasonal fruits and vegetables, baked goods, bread, eggs, honey, olives, pickles, prepared foods, healthy drinks, soaps, artisan creations and other favorites. Follow the market on Facebook for weekly vendor […] ...

Fall Festival in Peekskill, NY
Sat
Oct, 5
11:00 am - 5:00 pm
Peekskill Riverfront Green Park
Railroad Ave Peekskill, NY 10566

Peekskill Rotary’s Fall Festival

Join us on October 5th from 11am – 5pm at the beautiful Peekskill Riverfront for a day packed with fun! šŸ” Food Trucks šŸ» Beer Garden šŸŽØ Craft & Art Vendors šŸŽ¶ DJ & Live Music šŸŒ¶ļø Chili Cookoff šŸŽŸļø Raffles & Auctions šŸ¾ Pet Friendly šŸŽØšŸŽƒ Kidsā€™ Activities: Pumpkin Painting, Arts & Crafts, Maze, […] ...

Peekskill Racket Association Schedule
Sat
Oct, 5
12:00 pm
Depew Park
1 Robin Dr, Peekskill, NY 10566

Peekskill Racket Association: Adult Round RobinWeekly

Join The Peekskill Racquet Association for an afternoon of Adult Doubles Round Robin at Depew Park. The Peekskill Racquet Association is a 501(c)3 non-profit community organization dedicated to expanding access to tennis and racquet sports in the community. ...

Sat
Oct, 5
2:00 pm
Lincoln Depot Museum
10 South Water Street, Peekskill, NY 10566

Civil War Era & 19th Century Photography

DAGUERREOTYPES, AMBROTYPES, TINTYPES & MORE… Saturday, October 5, 2024 at 2:00 pm with Historian, Photography Collector and Lincoln Depot Museum Board Member Brian Caplan ...

Brian Regan performs at The Paramount in Peekskill, NY
Sat
Oct, 5
8:00 pm
Paramount Hudson Valley Theater
1008 Brown St, Peekskill, NY 10566

Brian Regan

Get ready for an uproarious evening of laughter as the legendary Brian Regan returns to Paramount Hudson Valley on October 5! Renowned by critics, fans, and fellow comedians alike, Brianā€™s comedic genius has earned him the title of ā€œThe funniest stand-up aliveā€ by Vanity Fair and ā€œYour favorite comedianā€™s favorite comedianā€ by Entertainment Weekly. With […] ...

Collage of Run For Cover logos
Sat
Oct, 5
9:00 pm
Gleasonā€™s
23 South Division Street, Peekskill, NY

Run For Cover

High Energy 90ā€™s & 2000ā€™s Party Cover Band rocks the Gleason’s stage. Great pizza, great pasta, great cocktails in an inviting atmosphere with us on the big stage! Get there early for dinner, stay for the show and drinks! Bring your friends because you do not want to miss this one! ...

Flier for Bicycle Sundays in Depew Park
Sun
Oct, 6
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 ...

Six square images of the players in The David August Sextet
Sun
Oct, 6
3:00 pm - 5:00 pm
BeanRunner Cafe
201 South Division Street, Peekskill, NY 10566

The Dave August Sextet

The Dave August Sextet includes highly accomplished musicians who present fresh arrangements and original compositions by pianist David August. The sextet includes: Mindy Saz, Kip Sophos, Norbert Goldberg, Andrew Beals and special guest, Julie Diesslin. $15 admission ...

Jeff Boyer's Big Bubble Bonanza in Peekskill, NY
Sun
Oct, 6
3:00 pm
Paramount Hudson Valley Theater
1008 Brown St, Peekskill, NY 10566

Jeff Boyerā€™s Big Bubble Bonanza

See the newest, funniest, zany spectacular from world-famous,Ā Guinness Book of World Records-holding, master bubble wrangler Jeff Boyer, as he takes bubbles to the max with big bubble flair. Mixing comedy, music, and interactive bubble-magic, Jeff engages and delights audiences of all ages. Itā€™s a sensory-friendly bubble extravaganza for the whole family! ...

Sun
Oct, 6
5:00 pm - 8:00 pm
Restaurant Row on N. Division
40 North Division Street, Peekskill, NY

Peekskill Summer Sessions: Dave Diedrich

Dave Diedrich, also known as the one-man show that must go on, Peekskillā€™s favorite Pianoman and Ludwig von Davehoven, is coming back to our little town in the Valley, armed with his keyboard, stellar voice, and killer repertoire. An excellent act to end the weekend. Welcome back, Dave!šŸŽ¶ ...

Last Minute Soulmates performing live on stage.
Fri
Oct, 11
9:00 pm
Gleasonā€™s
23 South Division Street, Peekskill, NY

Last Minute Soulmates

Join us for a night with one of the most talented bands around. Be prepared to dance the night away to songs you know performed with amazing originality! Originals/covers Rock Band from Beacon, NY. ...

The Lonely Leaves performing at the Birdsall House beer garden.
Sat
Oct, 12
9:00 pm
Gleasonā€™s
23 South Division Street, Peekskill, NY

Lonely Leaves

Peekskill’s premiere middle-aged boy band rocks the Gleason’s stage. This local indie band brings catchy originals and covers of hits that will keep your head bobbing all night long. ...

Guess The Weight of The Pumpkin at the Peekskill Farmer's Market
Sat
Oct, 26
8:00 am - 2:00 pm
Bank Street
Bank Street, Peekskill, NY 10566

Guess The Weight of The Pumpkin!

Guess the Weight of the Giant Pumpkin While Enjoying the Autumn Bounty Saturday, October 26, 2024, 8:00AM TO 2:00PM Visit the BID Booth to make Your Guess! Closest guess (without going over) wins a $100 GIFT CARD! FREE TO ENTER. Children accompanied by an adult: wear your costume and trick or treat at participating vendors. […] ...

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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!