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
The Addams Family
The Addams Family (1991)
OCT. 30 | 8:30 PM / OCT. 31 | 10 AM / NOV. 1 | 4 PM - $12 Kids & Seniors / $15 General Admission
1850 Second Ave.
Celebrate Halloween at Wayfarer Theaters with the classic 1991 version of The Addams Family! Catch a screening on October 30 (8:30 PM), October 31 (10 AM), or November 1 (4 PM). Plus, guests who arrive in costume will receive a FREE small popcorn!
Halloween Karaoke Party
Thriller, Monster Mash, Ghostbusters, and more. Start your spooky celebrations early at Steep Ravine Brewing Company on October 30 with a Halloween Karaoke Party.
Ravinia District Candy Stroll & Food Trucks
Ravinia District
Candy Stroll & Food Trucks
OCT. 30 | Trick-or-treat at participating businesses from 3:30-5 PM; then party in the park with food trucks & food and beverage vendors until 7 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.).
Exciting news for this year, we’re bringing several food trucks and beverage vendors back to Jens Jensen Park! For the first time, you can enjoy delicious food from local trucks in the park until 7 PM.
Trick-or-treaters will collect candy from participating businesses while strolling the streets and enjoying the festive fall décor installed throughout the District. Participants can pick up a free trick-or-treat bag in Jens Jensen Park, where they will find goodies, a DJ spinning Halloween music, a guessing game, vendors, and more. Candy strollers will also appreciate fun selfie opportunities with decorated pumpkins in front of Ravinia District 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 - 8 PM | FREE ENTRY
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.
There is no entry fee for this event, and tickets / RSVPs are not required.
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!
Mandala Pumpkin Sip & Paint
Celebrate the season while painting your very own Pumpkin using a mandala dot art technique — perfect for festive home décor. Sip, relax, and enjoy the vibes while getting crafty at Lynfred Winery. The $35 fee includes:
🎨 Guided Painting: Step-by-step instructions (no art experience needed)
🎃 All Supplies will be provided for you to use!
🏡 Take Home Décor: Leave with your very own hand-painted pumpkin — perfect for a Fall décor or a unique seasonal gift.
*Finished foam/plastic pumpkin
**Wine not included in ticket price. Glasses may be purchased at the event.
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
Bubbleween
Bubbles Academy
Bubbleween
OCT. 24 | 10 AM - 12 PM | $25
Bubbles Academy - 1736 First St., Ste. 102B (rear)
Children ages 0 months - 6 years are invited to join Bubbles Academy for the annual Bubbleween costume party! Enjoy a special live concert by Miss Anna at 10:45 AM, spooky crafts, open play, a monster mash dance party, a costume parade, and light refreshments.
$25 per child, up to two adults allowed per child.
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.
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+
Paws & Candy Adoption Event
Pets4Life
Paws & Candy Adoption Event
OCT. 23 | 3 PM - 4:30 PM | FREE
Pets4Life - 661 Central Ave.
Double the treats, double the fun! Stop by Pets4Life on October 23 for an extra-special Halloween adoption event with Orphans of the Storm. Grab some candy for the kids and meet your new best fur-iend. No tricks, just pure love!
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+
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
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
Halloween Candy & Wine Flight
Halloween Candy & Wine Flight
OCT. 16 - OCT. 25 | $17 Wine Club Members / $22 Non-Members
1823 St. Johns Ave.
This Halloween season, indulge your inner child with a grown-up twist. Lynfred Winery is offering a Halloween Candy Pairing Flight from October 16 - October 25. This wine flight brings together four handcrafted Lynfred wines with classic candies for a playful and surprisingly delicious tasting experience.
Whether you’re here for the nostalgia or the nuanced flavors, this flight is a festive and sweet way to celebrate the season.
Witches Brine Workshop
Park District of Highland Park
Witches Brine Workshop
OCT. 8 | 5:30 PM - 6:45 PM | $25
Rosewood Beach Interpretive Center - 883 Sheridan Rd.
Get into the Halloween spirit while learning the art of pickling! Discover the science behind brining, create your own delicious pickled vegetables, and take home a jar of spooky-season flavor.
Pre-registration required. All participants, children and adults, must register for the program. Children must be accompanied by a paid registered adult. Program is indoors.
Ages 8+
Scarecrow Trail
Scarecrow Trail
SEPT. 25 - OCT. 10
Downtown Highland Park
The third annual Scarecrow trail throughout Downtown Highland Park features over THIRTY uniquely decorated scarecrows! Explore the scarecrow displays before casting a vote for “Best in Show Scarecrow.” The Scarecrow Trail will run from September 25 - October 10; the winner will be announced during the 5th-annual Stews & Brews, taking place at Port Clinton Square.