Spooky Season in Highland Park
Pumpkins, treats, gatherings, decor, and more… Let our guide to Spooky Season raise your spirits. Check back often, new entries are added weekly!
Events
Downtown Highland Park
THROUGH OCT. 31 | FREE
Take a self-led, leisurely walk through Downtown Highland Park’s Scarecrow Trail to see over two dozen festive scarecrows, each uniquely decorated by local businesses.
Howl-O-Ween
Whether your pets bark or meow, there's something to howl about at Pets4Life this month! Through October 31, submit a photo of your furry friend (or bring them in for a photo) in their best Howl-O-Ween costume for a chance to win a paw-some prize. The fur-st place winner will be announced November 1. Need a costume or grooming? Pets4Life can help with that, too! Take 15% off of all pet costumes October 25.
Plus, be sure to stop by Pets4Life on October 23 between 3 PM - 6 PM as part of the Downtown Highland Park candy stroll.
Two-Sentence Horror Stories
Got a super short, super creepy story? Share it with the Library! Stop by the Youth Services desk to pick up your entry form. Come back on Halloween to see your entry among Highland Park’s most spine-tingling tales.
Meet the Author
If you liked What We Do in the Shadows, you should buy this book. If you hated Twilight, you should also buy this book. Meet author Lindsay Merbaum on October 14 at Secret World Books and pick up your very own copy of Vampires at Sea.
Immortal beloveds Rebekah and Hugh are on vacation! Against a backdrop of ongoing war, this pair of chic emotional vampires from San Francisco set off on a Black Sea Cruise, eager to relax and feast upon their fellow passengers' desires and sorrows. All that changes when their worlds collide with social media influencer, Heaven.
Park District of Highland Park
Heller Nature Center - 2821 Ridge Rd.
OCT. 16 | 10 AM - 11 AM | $15 Resident / $18 Nonresident
Search the mini pumpkin patch at the Heller Nature Center and pick the perfect pumpkin to make your own. Then, let your creativity shine—paint, stickers, googly eyes, and more will be on hand for you to decorate a one-of-a-kind pumpkin masterpiece to take home!
Park District of Highland Park
Park Fitness - 1207 Park Ave. W
OCT. 18 | 1 PM - 2:30 PM | $15 Resident / $18 Nonresident
Dive into a world of whimsy and wonder with the Park District at the Pumpkin Pool Splash on October 18! 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. This afternoon filled with pumpkin-themed delight will leave you thrilled and soaked in unforgettable memories!
Ghost Stories from the Fort
Join Matt Fuller and the rest of the Fort Sheridan Historical Society on October 18 at 6 PM beneath the water tower to hear spooky (but family-friendly!) tales about Fort Sheridan's history. Bring your own chair or blanket, light snacks will be provided.
Halloween Contests
Goodies has a whole week of Halloween fun planned for little goblins and ghoulies 10 years and younger. Stop by every day for new and exciting happenings and contests!
Oct. 20 | Find the special gumball or pick the lucky candy from the mystery bag!
Oct. 21 | Guess how many candies
Oct. 22 | Wear your best Halloween costume for a chance to win a Goodies gift card
Oct. 23 | Surprise drop!
Oct. 24 | I spy...
Show your bones! Create a skeleton hand with the Library just in time for spooky season. Pick up materials at the Youth Services Desk while supplies last.
Downtown Highland Park Halloween Happenings
Port Clinton Square | 600 Central Ave.
Renaissance Place | 1849 Green Bay Rd.
Michael’s Grill & Salad Bar | 1879 Second St.
OCT. 23 | 3 PM - 6 PM
Downtown Highland Park has an afternoon of spooktacular, family-friendly Halloween fun planned for October 23. You won't want to miss these festivities.
3 PM - 5 PM | Kids can trick-or-treat store-to-store and fill their buckets full of candy from participating downtown businesses.
3 PM - 6 PM | Find festive live music, DJs, and face painters at Port Clinton Square (600 Central Ave.) and Renaissance Place (1849 Green Bay Rd.).
4:30 PM - 7 PM | Enjoy a Halloween bash buffet and costume contest at Michael's Grill & Salad Bar (1879 Second St.).
5 PM | Bring your costumed dog to Port Clinton for a doggy costume contest with special judge, Jon Levey of Highland Park Bank & Trust.
Jens Jensen Park - 540 Roger Williams Ave.
OCT. 24 | 3:30PM - 5PM | FREE
The annual Ravinia District Halloween Candy Stroll returns on Friday, October 24, 2025! Pick up a candy collection bag at Jens Jensen Park (540 Roger Williams Ave.) Visit participating businesses within the Ravinia District for trick-or-treating, then head back to Jens Jensen Park for tons of fun, games, and a contest to guess the weight of a giant pumpkin!
Park District of Highland Park
Club Pickle & Padel | 2205 Skokie Valley Rd.
OCT. 24 | 5 PM - 9 PM | FREE premier membership / $10 standard membership / $15 non-member
All ages and levels are invited to join the Park District for a spooktacular night on the courts! Wear your favorite costume (encouraged, not required) and enjoy festive open play with friends. There will be themed music, treats and plenty of pickleball fun!
Park District of Highland Park
River’s Edge Mini Golf | 2205 Skokie Valley Rd. | 847.831.3810
OCT. 25 | 9 AM - 7 PM | FREE
Dress in costume and receive a free round at River’s Edge Mini Golf on October 25, no reservations necessary!
1736 First St., Ste. 102 | 312.944.7677
OCT. 25 | 10 AM - 12 PM | $30
The annual Bubbleween Bash returns to Bubbles Academy on October 25! Enjoy snacks, spooky singing time with Ms. Anna, photos with TK Photography, and more!
Can't get enough Bubbleween? Check out Bubbleween Halloweek - dress your little one in their costume for a whole week of drop-in classes October 27 - October 31.
It’s spooky season at the Library! Head over to Curt’s Cafe on October 25 to discuss one of the most feared and adored monsters and his eternal legacy in cinema. From classic portrayals such as Schreck, Lugosi and Lee to more contemporary performances like Oldman, Cage, and Skarsgård.
Romantic to terrifying. Who's your favorite? What’s their appeal?
There are numerous Dracula movies you can find through the library. If you need assistance with acquiring or accessing titles, feel free to drop by the Adult Services desk, or call 847.681.7031 or email ref@hplibrary.org.
Snacks provided by the library.
Meet the Author: Keyana Loves Halloween
1774 Second St. | 847.469.4875
OCT. 25 | 2 PM | FREE
Join Secret World Books for a Halloween-themed family story time on October 25. Bestselling author Natasha Anastasia Tarpley will share Keyana Loves Halloween, the latest in her delightful series featuring the imaginative and creative-problem-solving Keyana.
Park District of Highland Park
Hidden Creek Aqua Park - 1220 Fredrickson Plaza | 847.831.3810
OCT. 30 | 3:30 PM - 5 PM | FREE
Join the Park District in celebrating the season with a free, family-friendly Trunk or Treat event at Hidden Creek Aqua Park on October 30! Kids are invited to trick-or-treat from car to car, collecting treats from creatively decorated trunks hosted by Park District staff and local community groups. Costumes are encouraged!
Hotel Transylvania
Enjoy a family-friendly night with Arbor Terrace on October 30. Bring a chair and a blanket while enjoying a special screening of “Hotel Transylvania” on the outdoor screen. Plus, enjoy tasty treats, face painting, and a pumpkin to take home. This event is free, but please RSVP by calling 847.681.3636.
Halloween Party & Candy Weigh-In
582 Roger Williams Ave. | 847.780.8127
OCT. 31 | 7 PM
Looking for post-Trick or Treating plans this Halloween?! Steep Ravine Brewing Company has got you covered! There’s a ghoulishly good time ready and waiting for you once the sun goes down on October 31 - complete with prizes for the best costumes and most candy! Come prepared to have a grand old spooky time!
Dining
Candy Apples
1853 Second St. | 312.733.2700
Terry's Toffee has a delicious take on this classic Halloween treat! Caramel apples are back - bite into a crisp, tart, juicy apple smothered in rich caramel and decked out in spooky Halloween bling. Each handcrafted apple is made with love (and a pinch of Halloween mischief). These are only available in-store, so stop in before they're gone!
Halloween Fluff Cups
610 Central Ave., Ste. 160 | 847.504.9019
Halloween fluff cups have been summoned back to the land of the living at Bright Bowls! Sink your fangs into these decadent cups made of vegan white chocolate, Bright Butter, vegan marshmallows, and colored with natural curcumin.
Halloween Candy Pairing
Who said Halloween candy was only for kids? Through October 31 indulge in a spookily sweet wine pairing at Lynfred Winery: sparking VDC rose & gummy bears, riesling 2024 & Skittles, petit verdot 2019 & Twix, and plum wine & Reese’s Peanut Butter Cups.
Fall Flavors
1888 First St. | 847.433.1411
Fall treats have arrived at Once Upon A Bagel! Check out jack o'lantern cookies (pictured), pumpkin pecan loaves, pumpkin spice scones and English muffins, and cranberry orange scones. Yum!
Boorrito is Back!
1766 Second St. | 847.748.8086
Available through October 31
The Boorrito from Curt’s Cafe has been resurrected! Get it now before it returns to the spirit world on October 31. This delicious treat is comprised of seasoned ground beef, lettuce, corn, black beans, pico de gallo, salsa verde, avocado, and chihuahua cheese, all wrapped in a flour tortilla and served with chips and a pickle.
Retail
Halloween Signature Assortment
652 Central Ave. | 847.432.0652
Don't miss out on the Halloween-themed signature assortment from Goodies. This delicious tray is packed with cookies, pretzels, chocolates, marshmallows, and more!
Halloween Collection
1780 Green Bay Rd. | 847.681.0200
Find candles, tablescapes, decor, home goods, accessories, and more to enliven your home.
Contact Marketing Coordinator, Diane Larson, to have your Halloween event, menu, or decor featured.