An hour north of New York City is a place where small-town charm meets urban vibes this holiday season. It’s a little city on the Hudson River called Peekskill. It’s not just wonderful—it’s wonderfully edgy. This winter, the Hudson Valley’s hidden gem transforms into a twinkling playground of fun things to do, and Peekskill’s artistic spirit can be felt throughout. It’s like your favorite Hallmark Christmas Movie but arthouse. Embrace the unexpected and discover why “It’s a Wonderful Peekskill” isn’t just a slogan—it’s a Hudson Valley holiday experience that we hope will become your new winter tradition.
Peep some of Peekskill’s holiday happenings:
Kinship Co-Working
116 Washington Street, Peekskill, NYDog Adoption Holiday Event
HolidayWeekender PickMeet adorable, adoptable dogs looking for their forever homes. Come by whether you’re ready to expand your family or just want to enjoy some puppy love. Wrap up your holiday shopping at Kinship’s gift shop while you’re at it! ...
The Artist Spot
925 South St, Peekskill, New York 10566Antonia Arts Holiday Shop
HolidayWeekender PickJust in time for the holidays! Antonia Arts invites you to an incredible weekend filled with unique gifts, handmade treasures, and artistic creations. Celebrate diversity and shop local! 📅 Save the date: 🗓️ Sat, Dec 21 & Sun, Dec 22 ⏰ 1 PM – 6 PM 📍 925 South Street, Peekskill, NY Support talented artists […] ...
Ford Piano Building
15 South Division Street, Peekskill, NYBig Art Show
HolidayWeekender PickThe Peekskill Arts Alliance will display large-scale works by its members in the Ford Piano Building. The Big Art Show will then be open every Friday through Sunday during the month of December. To see the large works of art visit the Big art show on Fridays from 5:00-7:00 p.m., Saturdays from 1:00 – 7:00 […] ...
BeanRunner Cafe
201 South Division Street, Peekskill, NY 10566Connected! For the Holidays
HolidayRichie Goods is one of the most versatile and accomplished bass players on the scene. He has recorded and toured with the Headhunters, Louis Hayes and the Cannonball Adderley Legacy Band, Lenny White, Mulgrew Miller, Whitney Houston, Christina Aguilera and Chris Botti to name a few. Chien Chien Lu is a vibraphonist, percussionist, and composer […] ...
Birdsall House
970 Main St, Peekskill, NY 10566Crazy Christmas Hat Party
HolidayWeekender PickJoin us for our 1st Annual Crazy Christmas Hat Party. You read it right. Don your weirdest Christmas hat and head over to Birdsall for drink specials and a chance to win prizes for your holiday headwear. Make a reservation ...
NY Firehouse Grille
63 Welcher Ave, Peekskill, NY 10566Holiday Onesie Party
HolidayWeekender PickIt’s that time of year again… the NY Firehouse Grille **Annual Holiday Onesie Party** is BACK! 📅 **When:** Saturday, December 21 at 9pm 📍 **Where:** NY Firehouse Grille 🎉 **Dress Code:** Onesies (the cozier, the better). Bonus points for holiday themes! 🎅🦌❄️ Come for the festive vibes, stay for the drinks, food, and onesie dance-offs. […] ...
Ford Piano Building
15 South Division Street, Peekskill, NYBig Art Show
HolidayWeekender PickThe Peekskill Arts Alliance will display large-scale works by its members in the Ford Piano Building. The Big Art Show will then be open every Friday through Sunday during the month of December. To see the large works of art visit the Big art show on Fridays from 5:00-7:00 p.m., Saturdays from 1:00 – 7:00 […] ...
Copperhead Club
137 North Water Street, Peekskill, NYLast Minute Holiday Market
HolidayWeekender PickA pop-up holiday market with local artists and vendors for anyone who waited to find the perfect gift (and everyone else too) ...
BeanRunner Cafe
201 South Division Street, Peekskill, NY 10566The Riverton Trio
HolidayWeekender PickPlaying classic holiday jazz just for you, Rich, Michael, and Chris each brings a much different history to their improvising and choice of tunes. They met through the Westchester Symphonic Winds and formed the trio in 2019. Rich has an M.A. in Classical Composition, Michael a B.A in Jazz Performance, and Chris brings a perspective […] ...
Gleason’s
23 South Division Street, Peekskill, NYA Very Peekskill Christmas w/ Steve Chizmadia
HolidayWeekender PickJoin us for a fun-filled holiday show for the whole family. Steve Chizmadia and guests Al Hemberger, Paul Beladino, and the NECS Youth Theater Ensemble for a Christmas sing and dance along event. Make your reservation now ...
Fin & Brew
5 John Walsh Blvd Peekskill, New York 10566Fin & Brew Feast of the 7 Fishes
HolidayFeast of the 7 Fishes, Fin & Brew style, on Christmas Eve! $110 Per Person for 6 Courses, $30 Additional for Wine pairing. ...
Birdsall House
970 Main St, Peekskill, NY 10566Birdsall House Christmas Day w/ Cal & Tim
HolidayJoin Cal & Tim on Christmas Day at the Birdsall bar starting at 6pm for drinks, homemade bread, vegan chili, plus a heaping dose of Christmas merriment and joy. We can’t wait to celebrate with you! ...
Kyle's Pub & Grille
810 Washington Street, Peekskill, NYPolar Plunge Social
HolidayWeekender PickJoin us for our Polar Plunge Social on Friday, 12/27 at @kylespub_ !! Register to plunge or bring your donation! Lite snacks & cash bar. Open to all! ...
Ford Piano Building
15 South Division Street, Peekskill, NYBig Art Show
HolidayWeekender PickThe Peekskill Arts Alliance will display large-scale works by its members in the Ford Piano Building. The Big Art Show will then be open every Friday through Sunday during the month of December. To see the large works of art visit the Big art show on Fridays from 5:00-7:00 p.m., Saturdays from 1:00 – 7:00 […] ...
Ford Piano Building
15 South Division Street, Peekskill, NYBig Art Show
HolidayWeekender PickThe Peekskill Arts Alliance will display large-scale works by its members in the Ford Piano Building. The Big Art Show will then be open every Friday through Sunday during the month of December. To see the large works of art visit the Big art show on Fridays from 5:00-7:00 p.m., Saturdays from 1:00 – 7:00 […] ...
Ford Piano Building
15 South Division Street, Peekskill, NYBig Art Show
HolidayWeekender PickThe Peekskill Arts Alliance will display large-scale works by its members in the Ford Piano Building. The Big Art Show will then be open every Friday through Sunday during the month of December. To see the large works of art visit the Big art show on Fridays from 5:00-7:00 p.m., Saturdays from 1:00 – 7:00 […] ...
Peekskill Riverfront Green Park
Railroad Ave Peekskill, NY 10566Polar Plunge
HolidayJoin us at Peekskill Riverfront Green on January 1, 2025, for the 12th Annual Polar Plunge benefiting the This Is Me Scholarship Fund! Ready to plunge? Register by EOD 12/30 at www.thisismefoundation.com. No walk-up registrations allowed. Spectators are welcome to cheer on our brave participants! Donations can also be made on our website. Special thanks to our […] ...