Events Calendar - Community News and Events
APRIL FIRST WEDNESDAY CONNECTIONS 2026
Join the Highland Park Chamber of Commerce for April's First Wednesday Connections event on April 2nd at 7:30 am at Bluegrass! Come to connect and network with your fellow Highland Park community business owners and associates while enjoying a delicious made-to-order omelet. We're thrilled to welcome back Ravinia Festival, who will share all of the exciting programming scheduled for the 2026 season! Register today to make sure you're in attendance for this can't miss event!
SAVE THE DATE: FASHION IN FULL BLOOM ENAZ
ENAZ Celebrates 2nd Annual Spring Runway Show with Special Guest Rachel Boedecker From fashion show to fundraiser, ENAZ is combining both to host an unforgettable evening of glam, style, Spring fashion, and shopping for a cause! On Wednesday, April 15th, from 5-9 PM, the 2nd Annual Fashion In Full Bloom Fundraiser will take place at Upside Events, (440 Central Ave. 2nd floor, downtown Highland Park). Benefits will go toward supporting The Chicago Lighthouse, a social service organization for people who are visually impaired, disabled and Veterans. The evening will include a pre-fashion show Haute Happy Hour from 5-6 pm for attendees to sip, shop, and savor the spring style. The actual Fashion Show will take place from 6:30-7pm and then the fun continues with post-fashion show activities where guests can shop for a cause and reminisce about the styles of the night. To top it off, special guest Rachel Boedecker of @thestyleeditco, will help style and dress the fabulous line up of local models and The Custom Tie Bar will be onsite so guests can create their own tie with brooches, patches, and more! Join us for an incredible evening with spring styles, trends, and support an amazing cause!
Jessica Redish : Director Spotlight
Wayfarer Theaters Highland Park will present a special Director Spotlight of short films by director, writer, and choreographer Jessica Redish on Sunday, May 3, 2026 at 4:00pm. The event will showcase a curated selection of Redish’s acclaimed comedic and musical short films, followed by exclusive previews of her newest work and a look at upcoming projects.
MAY FIRST WEDNESDAY CONNECTIONS 2026
Join us for an evening of networking and connection at our First Wednesday Connections event in the month of May! Stay tuned for more information. Date: Wednesday, May 6, 2026 Time: 5:00 - 7:00 PM Location: TBD Register today to reserve your spot! *Chamber members and non-members are welcome!
TAC Benefit and Fundraiser
Join us for a celebration of community and creativity featuring cocktails, hors d'oeuvres, and a curated silent auction to support our galleries, classes, scholarships, and community events. This year’s event highlights the incredible work of celebrity photographer Sandro Miller, featuring his series on members of Chicago’s historic Steppenwolf Theatre, and members of the Chicago Imagists group, Hairy Who. We look forward to seeing you there as we raise vital funds to keep the North Shore’s home for artistic discovery thriving.
HPHS STUDENT HONORS NIGHT 2026
Please join us at the Highland Park High School on Monday, May 18th for the Highland Park High School Student Honors Night! On this wonderful evening, the businesses of Highland Park recognize students from Highland Park High School by sponsoring scholarships to seniors. These deserving students represent potential business and community leaders of the future. We hope you'll join us as we congratulate their accomplishments and leave inspired by their outstanding character. All members of the community are welcome! No registration is required for the 6:30 pm program.
Northbrook Symphony: Romantic Essentials
Violinist Joshua Brown, a finalist in the Queen Elisabeth Competition finalist, presents the magnificent Brahms Concerto before the NSO closes its season with B
JUNE FIRST WEDNESDAY CONNECTIONS 2026
Join us for a morning of networking and breakfast at our First Wednesday Connections event in the month of June! Date: Wednesday, June 3, 2026 Time: 7:30 - 9:00 AM Location: TBD Register today to reserve your spot! *Chamber members and non-members are welcome!
JULY FIRST WEDNESDAY CONNECTIONS 2026
Join us for an evening of networking and connection at our First Wednesday Connections event in the month of July! Stay tuned for more information. Date: Wednesday, July 1, 2026 Time: 5:00 - 7:00 PM Location: TBD Register today to reserve your spot! *Chamber members and non-members are welcome!
SIDEWALK SALE 2026
We?re thrilled to invite businesses, vendors, artists, and restaurants to take part in Highland Park?s biggest shopping event of the summer ? the Annual Summer Sidewalk Sale! This highly anticipated, two-day event brings the sidewalks of downtown Highland Park to life with amazing deals, one-of-a-kind merchandise, interactive experiences, and community energy.
AUGUST FIRST WEDNESDAY CONNECTIONS 2026
Join us for a morning of networking and breakfast at our First Wednesday Connections event in the month of August! Date: Wednesday, August 5, 2026 Time: 7:30 - 9:00 AM Location: TBD Register today to reserve your spot! *Chamber members and non-members are welcome!
SEPTEMBER FIRST WEDNESDAY CONNECTIONS 2026
Join us for an evening of networking and connection at our First Wednesday Connections event in the month of September! Stay tuned for more information. Date: Wednesday, September 2, 2026 Time: 5:00 - 7:00 PM Location: TBD Register today to reserve your spot! *Chamber members and non-members are welcome!
OCTOBER FIRST WEDNESDAY CONNECTIONS 2026
Join us for a morning of networking and breakfast at our First Wednesday Connections event in the month of October! Date: Wednesday, October 7, 2026 Time: 7:30 - 9:00 AM Location: TBD Register today to reserve your spot! *Chamber members and non-members are welcome!
NOVEMBER FIRST WEDNESDAY CONNECTIONS 2026
Join us for an evening of networking and connection at our First Wednesday Connections event in the month of November! Stay tuned for more information. Date: Wednesday, November 4, 2026 Time: 5:00 - 7:00 PM Location: TBD Register today to reserve your spot! *Chamber members and non-members are welcome!
DECEMBER FIRST WEDNESDAY CONNECTIONS 2026
Join us for a morning of networking and breakfast at our First Wednesday Connections event in the month of December! Date: Wednesday, December 2, 2026 Time: 7:30 - 9:00 AM Location: TBD Register today to reserve your spot! *Chamber members and non-members are welcome!
HIGHLAND PARK CHAMBER OF COMMERCE HOLIDAY CELEBRATION 2025
Celebrate the Season with the Highland Park Chamber of Commerce! Get ready to enjoy festive bites, seasonal sips, and the company of friends old and new at the beautiful Summer Classics Home. We'll raise a glass to another year of thriving local businesses, meaningful connections, and shared successes.
