Calendar
What’s Happening?
There’s always something to see or do in Highland Park! Check out our calendar to plan your next visit.
Note: The sponsoring organization for each event is included in the event listing. The City does not sponsor or endorse events listed on the calendar except those attributed to the City of Highland Park. Please direct any questions to the sponsoring organization.
To have your Highland Park event featured, please email Marketing Coordinator Diane Larson.
Individual Event Listings
Boo Bash
Park District of Highland Park
Boo Bash
OCT. 17 | 3 PM - 5 PM | $10 resident / $12 non-resident
West Ridge Center - 636 Ridge Rd.
Put on your costume and head over to meet live spooky animals, make an edible candy potion, test your skills on a spooky gymnastics course, and visit our enrichment rooms for Halloween fun!
Registration is per child and all children must be accompanied by a non-registered adult.
Ages 2-13
Kids Night Out: The Great Pumpkin
Park District of Highland Park
Kids Night Out: The Great Pumpkin
OCT. 17 | 6 PM - 8 PM | $28
Heller Nature Center - 2821 Ridge Rd.
Drop the kids off at Heller Nature Center to explore science and nature with our naturalists, while you enjoy a nice dinner or anything else you might have planned for Sweetest Day. Kids will scoop, squish, and explore pumpkins—digging into the guts and seeds while creating sticky, messy, and even exploding science experiments! We’ll even feed them pizza!
Ages 5-12
Not-So-Spooky Spider Party
Park District of Highland Park
Not-So-Spooky Spider Party
OCT. 21 | 10 AM - 11 AM | $10 resident / $12 non-resident
West Ridge Center - 636 Ridge Rd.
Join the Park District for a not-so-spooky spider adventure as you read The Very Busy Spider, discover how spiders build their amazing webs, and move like spiders through interactive activities. Children will then create a fun spider-themed craft while strengthening fine motor skills, creativity, and imagination.
Registration is per child and all children must be accompanied by a non-registered adult.
Ages 2+
Halloween Open Play Pickleball
Park District of Highland Park
Halloween Open Play Pickleball
OCT. 23 | 5 PM - 9 PM | $10 Premier / $15 Standard / $20 Non-Member
Club Pickle & Padel - 2205 Skokie Valley Rd.
Dress up in your favorite costume — it’s encouraged but never required! Enjoy festive open play with friends, and show off your look for a chance to win our Best Dressed contest. The winner gets to pick any item from the pro shop, on us!
Stop by check-in for some candy, and every registered participant receives a complimentary drink ticket to keep the fun going.
Ages 21+
Scary Skate
Park District of Highland Park
Scary Skate
OCT. 23 | 7 PM - 8:30 PM | $10
Centennial Ice Arena - 3100 Trail Way
Join the Park District of Highland Park for a frightfully fun evening at Scary Skate, our community ice skating event celebrating Halloween! Come in costume and enjoy spooky music, festive decorations, and a ghoulishly good time on the ice.
All ages and skill levels are welcome—just bring your skates (or borrow a pair) and get ready for a chillingly cool night!
Food available for purchase.
Pumpkin Pool Splash
Park District of Highland Park
Pumpkin Pool Splash
OCT. 24 | 1 PM - 2:30 PM | $15 resident / $18 non-resident
Park Fitness - 1207 Park Ave. W
Dive into a world of whimsy and wonder at the Pumpkin Pool Splash! Experience an exhilarating splashdown as colossal pumpkins take the plunge into a sparkling pool, creating a mesmerizing spectacle of color and excitement. Get ready to make a splash of your own amidst the vibrant autumn atmosphere, where fun knows no bounds and laughter echoes through the air. Join us for a day of pumpkin-themed delight that will leave you thrilled and soaked in unforgettable memories!
Ages 3-12
Candy Stroll at Port Clinton
Port Clinton Square
Candy Stroll at Port Clinton
OCT. 29 | 3 PM - 6 PM | FREE
Port Clinton Square
Have fun exploring fall decor, selfie stations, and live music at Port Clinton Square on October 29. Plus, trick-or-treat at participating Port Clinton businesses!
Halloween Boo Bash
Renaissance Place
Halloween Boo Bash
OCT. 29 | 3 PM - 6:30 PM | FREE
Renaissance Place - 1850 Green Bay Rd.
Enjoy a DJ, face painting, a balloonist, candy, and tons more Halloween fun
Halloween Bash
Michael’s Grill & Salad Bar
Halloween Bash
OCT. 29 | 3 PM - 7 PM
Michael’s Grill & Salad Bar - 1879 Second St.
Michael’s Grill & Salad Bar is set to host the annual Halloween Bash on October 29. This open-house event is complete with games and activities for kids, a costume contest, an all-you-can-eat buffet, and a delicious s’mores bar.
Details on RSVP coming soon.
Ravinia District Candy Stroll
Ravinia District
Candy Stroll
OCT. 30 | 3:30 PM - 5 PM
Jens Jensen Park
Start your Halloween haul early with the annual Ravinia District Candy Stroll on Friday, October 30 from 3:30 - 5 PM. Visit participating businesses for yummy candy and take part in fun, fall activities at Jens Jensen Park (540 Roger Williams Ave.).
Stay tuned for more information!