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ENJOY HIGHLAND PARK
Stews & Brews
OCT. 10 | 4 PM - 9 PM | FREE
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Midwestern fan-favorite festival, Stews & Brews, returns to Downtown Highland Park for a fifth year on October 10 at Port Clinton Square (600 Central Ave.). Cool weather means hearty comfort foods and hot beverages; Stews & Brews is the perfect event to warm your body and soul! Wrap up the City’s 2026 event season with savory stews and delicious brews, live music, and a cozy atmosphere.
Stews & Brews is not your ordinary chili cook-off or craft beer fest. This free, all-ages event offers attendees an array of cold weather comfort foods like chili, pozole, lamb stew, beef stroganoff, Hungarian goulash, potpies, and a variety of soups. Attendees can pair their dish of choice with dozens of unique brews including craft beers, spiced wine, hot toddies, mulled ciders and more!
Be sure to vote for your favorite stew and your favorite brew! Winners will be announced at 8:30 PM.
Get ready for more food, more music, and even more fun for 2026!
New for 2026: Ramp up the cozy with even more fire pits and heat towers! Plus, enjoy extended event hours with special children-focused programming from 4 PM - 6 PM, and satiate your sweet tooth with s’mores.
Port Clinton Square - 600 Central Ave.
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IN THE PLAZA
4 PM - 4:30 PM | Mary Macaroni
4:30 PM - 5 PM | K-Pop Demon Hunters
4 PM - 7 PM | FREE face painting, airbrush tattoos, and balloon art creations, plus meet & greets with Snow White's Evil Queen, Elphaba, and Darth Vader
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ON THE MAIN STAGE
4 PM - 5 PM | DJ Madrid
5 PM - 6:45 PM | 88 Keys Dueling Pianos
7:30 PM - 9 PM | Libido Funk Circus
| | PARTICIPATING RESTAURANTS | | THANK YOU TO THIS YEAR'S SPONSORS! | | |
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SECRET WORLD BOOKS
Banned Books
Get Together
OCT. 2 | 2 PM
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This Banned Books Week, Secret World Books is teaming up with Libro.fm and SilentBookClub to host a Banned Books Read-In to protest book censorship. Gather together on October 4 to read and take action against book bans. Bring your own read, buy a new challenged book, or grab a used book from Secret World Books' banned books box, and celebrate the freedom to read with the community! Attendees will also receive a free audio copy of either Banned Together or How to Defend Books and Why.
FREE
1774 Second St. / 847.469.4875
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PETS4LIFE & BRIGHT BOWLS
Doodles & Bowls
OCT. 3 | 10 AM - 2 PM
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Calling all doodles, near and far! Join Pets4Life, Bright Bowls, and Goddess Groom for Doodles & Bowls on October 3. See just how many doodles can gather in one place to celebrate one of the most perfectly adorable pup companions. Enjoy beautiful nourishment to keep your pups happy and energized, fun photo opportunities with your furry friends, and free vouchers for future nail trims provided by Goddess Grooms.
Port Clinton Square - 600 Central Ave.
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YANA'S SPEAKEASY
Sofar Sounds: Live Music Night
OCT. 8 | 8 PM
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Sofar Sounds is coming to Highland Park! Enjoy an intimate live music experiene on October 8 at Yana’s Speakeasy, featuring three secret artists across multiple genres. The lineup stays a surprise until the show; just grab a ticket, show up, and discover something new. Doors open at 7:30 PM
$30
465 Roger Williams Ave. / 847.322.9863
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ENJOY HIGHLAND PARK
Halloween Happenings
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Pumpkins, treats, gatherings, decor, and more… Let our guide to Spooky Season raise your spirits. We've put together a guide on where to find the best Halloween fun this year without ever leaving Highland Park. New entries are added to the guide weekly, so check back often!
📸: Start your Halloween haul early with the annual Ravinia District Candy Stroll on Friday, October 30 from 3:30 PM – 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 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.
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OVER THE TOP
Kinross Trunk Show
THROUGH OCT. 3
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Shop Over the Top's Kinross Trunk Show through October 3. Check out Kinross' expansive selection of cashmere, cotton, silk, blends and coats. Plus, take 20% off of all in-stock Kinross and all orders.
1866 First. St. / 847.433.3150
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MY SISTER'S CIRCUS
Planet by Lauren G. Trunk Show
THRU OCT. 8
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Get an exclusive look at Fall/Winter 2026 styles from Planet by Lauren G now through October 8 at My Sister's Circus . Shop this season's hottest styles, fabrics, and colors and make sure your wardrobe is cool-weather ready!
599 Elm Pl. / 847.432.7433
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RAVINIA DISTRICT
Tailgate Tour
NOW THROUGH OCT. 11
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Get ready for a brand new way to celebrate fall, football, community, and the Ravinia District this year: the all-new Ravinia District Tailgate Tour!
Visit participating businesses, complete free activities and earn a sticker for your Tailgate Tour card. Completed cards will be entered for a chance to win a prize pack to local businesses, valued at approximately $500.
Bring your friends and family, enjoy the football-themed atmosphere and discover more of what makes the Ravinia District such a special place to shop, dine and gather.
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1. Pick Up Your Ticket
Get a free Tailgate Tour ticket at a participating pickup location. See pickup & drop-off locations below:
2. Visit, Play and Collect Stickers
Walk along Roger Williams Avenue and visit participating businesses. Complete the activity offered at each stop to earn a sticker for your ticket. No purchase is necessary. Find participating businesses here.
3. Drop Off Your Ticket and Enter to Win
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MATCHMAKER BOOKSHOP
Meet the Author: Rioghnach Robinson
OCT. 10 | 6 PM - 8 PM
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Join Matchmaker Bookshop on October 10 in welcoming Rioghnach Robinson, in conversation with Cara Tanamachi, for the release of her adult debut novel, Bad Words!
Synopsis: Parker Navarro’s debut novel was meant to define his career - until critic Selina Chan’s blistering review made it the flop of the decade. Four years later, his new book is his shot at redemption; for Selina, reviewing him again is a professional risk she can’t refuse. When her second takedown ignites a viral feud, both their fortunes shift overnight. But as the literary world feeds on their public sparring, a quieter dialogue begins; one that challenges everything they thought they knew about success, sincerity, and each other.
$35
1891 Second St. / 847.926.7554
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WAYFARER THEATERS
Chicago Premiere:
The Kid Officer
OCT. 13 | 6 PM - 7:20 PM
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Join Wayfarer Theaters for the Chicago premiere of the award winning documentary The Kid Officer. Following the screening there will be a Q&A with the film's director John Rokosny.
The Kid Officer tells Freddy Biermann’s extraordinary story of survival and resilience. But at the heart of the film is also an unexpected story of friendship. As a boy in British-controlled Palestine, Freddy formed a close friendship with an Arab boy, a relationship that became an important part of his remarkable childhood story. For the Highland Park screening, history becomes intensely personal. While in Vienna, Freddy's sister Mary, was the best friend of a young girl named Fini. Fini’s granddaughter, Highland Park resident and Style Shack co-owner Sherry Levin, helped bring the film to the North Shore after discovering the remarkable connection between the documentary’s subject and her own grandmother.
$20
1850 Second St. / 872.873.1030
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NEW BUSINESS SPOTLIGHT
SweatHouz
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SweatHouz Highland Park brings modern contrast therapy to Chicago’s North Shore with private infrared sauna and cold plunge suites designed for relaxation, recovery, and overall wellness. SweatHouz is conveniently located at 1899 Second St. in Downtown Highland Park. Each private suite gives you uninterrupted access to an infrared sauna and cold plunge, allowing you to experience contrast therapy at your own pace. First-timers can enjoy a special introductory session offer of just $35!
1899 Second St. / 847.861.0070 / www.sweathouz.com
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HIGHLAND PARK POETRY
October Featured Poets & Open Mic
OCT. 10 | 4 PM - 6 PM
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Highland Park Poetry welcomes October's featured poets Charlotte Digregorio and Trudy Kleckner at Secret World Books on October 10. Charlotte is the author of Wondrous Instruction and Advice from Global Poets: How to Write and Publish Moving Poems and Books and Publicize Like a Pro, while Trudy is the author of Recalibrations. A poetry open mic will follow.
FREE
Secret World Books - 1774 Second St.
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NORTON'S RESTAURANT
Sip & Seek
Singles Night
OCT. 14 | 4 PM - 7 PM
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Norton's Restaurant is excited to introduce Sip & Seek, an evening designed for local singles to mingle and make new connections in a relaxed setting. Drop in on October 14 for special craft cocktails and iconic 80s tunes. Meet new people, enjoy delicious food, and revel in nostalgia!
1905 Sheridan Rd. / 847.432.3287
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ENJOY HIGHLAND PARK
Women-Owned Small Business Month
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October is National Women-Owned Small Business Month! Each week, we'll be highlighting one of Highland Park's amazing women-owned businesses. Find an extensive list of women-owned businesses throughout Highland Park here.
📸: Inside Las Torres Mexican Restaurant you'll enjoy authentic Mexican cuisine made from scratch daily. Whether you've got a taste for tacos, burritos, fajitas, enchiladas, or salads, each menu item is created with care, using only the highest quality fresh ingredients. Recipes are traditional and authentic, meaning you get a true taste of Mexico in every bite.
1910 First St. / 847.926.7689
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UPSIDE EVENTS
Second Story Market
OCT. 16 & 17 | 11 AM - 4 PM
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Upside Events will host the second annual Second Story Market on October 16 and 17. Shop a variety of one-of-a-kind and hand-selected upcycled, resale, and vintage items from a dozen unique vendors. Find home goods, clothing, accessories, and more.
Suggestion donation of $10 to benefit North Shore Exchange
440 Central Ave., 2nd Floor
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SOULSHINE BOUTIQUE & HEALING SANCTUARY
Nine Days of Navratri
OCT. 15 | 6:45 PM - 8:30 PM
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Navratri (sometimes spelled Navaratri) is a nine-night tradition, rooted in ancient Indian culture, honoring the feminine energy in its many forms. This year, Join Ramaa Krishnan and Laura Rategan at Soulshine Boutique & Healing Sanctuary on October 15 for a beautiful evening of meditation, a smudging blessing, crystal healing, and a self-love sound bath centered around your heart chakra. Together, you'll explore the feminine energy of compassion as well as the sacred practice of loving another deeply while remaining rooted in love and connection with yourself, all while drawing inspiration from the Goddess Lakshmi.
$44
459 Central Ave., 2nd Floor / 224.805.1390
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HIGHLAND PARK FIRE DEPARTMENT
STOP THE BLEED® Training
OCT. 6 | 9 AM - 11 AM | FREE
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STOP THE BLEED® is designed to help you gain the ability to recognize life-threatening bleeding and intervene effectively. The person next to a bleeding victim may be the one who’s most likely to save him or her. Take the course and become empowered to make a life or death difference when a bleeding emergency occurs. There is no fee for this course.
To register for the STOP THE BLEED® course, please call the Fire Department at 847.433.3110 or email fire@cityhpil.com.
Station 33 - 1130 Central Ave.
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HIGHLAND PARK STRINGS
Porgy & Bess and
The New World
OCT. 18 | 3 PM
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Cristian Gibbs is a sophomore pursuing a BFA in Musical Theatre at Carnegie Mellon University. Cristian will join Highland Park Strings on October 18 at Highland Park High School for a free concert. Selections from the concert include:
Morton Gould - American Salute
George Gershwin - Selections from Porgy and Bess feat. Cristian Gibbs, Tenor
Antonin Dvorak - Symphony No. 9, Op. 95 (from The New World)
FREE
Highland Park High School - 433 Vine Ave.
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HIGHLAND PARK COMMUNITY HOUSE
Pilgrim Chamber: Russian Masters
OCT. 18 | 3 PM
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Pilgrim Chamber Players is set to open its 29th anniversary concert season on October 18 at the Highland Park Community House with Russian Masters. Russian Masters will feature Chicago Symphony Orchestra violinist Matous Michal, cellist Steven Honigberg, and pianist Joseph Yungen performing works by Pyotr Tchaikovsky, Sergei Rachmaninov, and Dmitri Shostakovich. There will be a reception after the concert.
$20 Adults / $10 Children
1991 Sheridan Rd.
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TRINITY EPISCOPAL CHURCH
Artemis Chamber Orchestra: Octets
OCT. 18 | 3 PM
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The Artemis Chamber Orchestra will perform a free concert on October 18 at Trinity Episcopal Church. Enjoy renditions of the following pieces:
Dmitri Shostakovich
Two Pieces for String Octet, Op. 11
Ari Fisher
Children's Suite
Felix Mendelssohn
Octet in E-flat Major, Op. 20
FREE
425 Laurel Ave.
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CITY OF HIGHLAND PARK
Heat Pump & Electrification 101
OCT. 14 | 6 PM | FREE
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Curious about heat pumps, induction stovetops, and general electrification of the home? Then join us for an intro to the transformative world of heat pumps and electrification presented by Aaron Stash from the Electric Homes Company. Learn about heat pumps and the benefits they can provide in savings, comfort, safety, and reducing your greenhouse gas emissions. Join us in person on Oct. 14, 6 PM at City Hall or via live Zoom option. Register for the event by clicking the button below.
City Hall - 1707 St. Johns Ave.
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BRAESIDE MARKET
Farmers Market
SUNDAYS THRU OCT. 25 | 9 AM - 1 PM
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Join Braeside Market every Sunday through October 25 for a community-focused outdoor market. Held outdoors in Braeside Market's green space, this weekly market features local growers, bakeries, and artisans. Bring your own bag!
55 St. Johns Ave. / 773.705.3302
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LYNFRED WINERY
Tuesday Takeout
Takeover
TUESDAYS IN OCTOBER
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Have you ever wished you had the perfect wine to pair with a delicious takeout meal from your favorite Highland Park restaurant? Check out Tuesday Takeout Takeover at Lynfred Winery! Each Tuesday in October, stop by Lynfred with your same-day receipt from a Highland Park restaurant. Lynfred will provide pairing suggestions and take $2 off the purchase price of your wine.
1823 St. Johns Ave. / 847.780.3853
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RAVINIA FARMERS MARKET
48th Annual Ravinia Farmers Market
WEDNESDAYS THROUGH OCT. 28 | 7 AM - 1 PM | FREE
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The Ravinia Farmers Market is well into its 48th season, bringing fresh local foods, live music, and community fun to Jens Jensen Park every Wednesday through October 28.
Featuring more than 35 vendors throughout the season, the market offers a wide variety of seasonal produce, artisan food products, specialty prepared foods, flowers and plants, local health and wellness products, handmade goods, community organizations and more. Weekly live music and rotating pop-up activities add to the relaxed, welcoming atmosphere that has made the Ravinia Farmers Market a longtime Highland Park tradition.
Set beneath the trees in Jens Jensen Park, the market has become a weekly gathering place where families, friends and neighbors can shop, support local farmers and businesses, enjoy ready-made foods, listen to live music and linger in the park on a summer morning.
Returning this season is free Yoga in the Park with Lori Fink of YogaSix Highland Park each week at 11 AM on the lawn beneath the trees in Jens Jensen Park.
Additional complimentary family-friendly activities throughout the season will include balloon art as well as select face painting dates and other entertainment TBA, all presented by Chicago-based entertainment company Share Happiness. Market visitors can also enter weekly free prize drawings featuring Ravinia Festival concert tickets on select weeks, along with giveaways and prizes from local businesses and community partners.
Weekly music at the market is provided by Life Rhythms, and sponsored by the Highland Park Community Foundation. Additional market sponsors and supporters include the City of Highland Park, the Park District of Highland Park, the Ravinia Neighbors Association, Presence, Wayfarer Theaters, and Keyth Security.
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THE ART CENTER
Figure Drawing
Drop In
OCT. 8 | 6:30 PM - 9 PM
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Drop in to The Art Center's Cortesi Gallery on October 8 for figure drawing. Bring your own drawing materials, set up on one of the provided easels or drawing boards, and start sketching!
$20 Members / $25 Non-Members
1957 Sheridan Rd. / 847.432.1888
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HIGHLAND PARK PUBLIC LIBRARY
Banned Books Read-In
OCT. 6 | 6 PM - 8 PM
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Banned Books Week is an annual event that highlights the value of free and open access to information. Join the Library this year on October 6 to celebrate the freedom to read with a Banned Books Read-In. Grab a book from a stack of banned and challenged books provided by the library. Quiet reading time will be from 6 PM - 7 PM. Have questions about Banned Books, or want to discuss what you've read? Stick around for the discussion taking place from 7 PM - 8 PM. Every participant will receive a free audiobook from Libro.fm.
FREE
494 Laurel Ave. / 847.432.0216
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