Name: Highland Park Wine Stroll
Start: 2026-06-18T17:00:00-05:00
Location: Downtown Highland Park

Downtown Highland Park

Sip, Shop &amp; Stroll Through Downtown Highland Park
The Highland Park Wine Stroll returns Thursday, June 18 for an evening of wine tastings, exclusive shopping deals, light bites, giveaways, and fun experiences at local businesses throughout downtown Highland Park.
Guests will enjoy wines from Vin Chicago and Lynfred Winery while exploring participating shops and special pop-up experiences along the stroll. New this year: a limited VIP Wine Experience featuring exclusive wines, live music, and light bites before the main event begins.
Perfect for a girls’ night out, date night, or summer evening with friends.
Thursday, June 18 5:00 PM – 7:30 PM (VIP starts at 4:30 PM) Downtown Highland Park Limited tickets available on Eventbrite Must be 21+ for wine tastings

Local Event: Highland Park Wine Stroll

Lake County

Rachel Barnes

Chicago Metropolitan Area

Highland Park

Illinois

Highland Park Wine Stroll

Sip, Shop & Stroll Through Downtown Highland Park
The Highland Park Wine Stroll returns Thursday, June 18 for an evening of...

Trinity Episcopal Church

A civil debate between national political figures. Sponsored by The Highland Park Art Center. Free admission.

Local Event: Debate without Hate

Debate without Hate

A civil debate between national political figures. Sponsored by The Highland Park Art Center. Free admission. 

Do-Rite Donuts is coming to you on Saturday, May 23rd! Enjoy a wide variety of freshly baked artisanal donuts in unusual flavors - with seasonal, gluten-free, and vegan options available.
Order by 10pm on Friday. Your order will be available for home delivery between 6:30-10:00am.
Twice is nice! Place two or more orders for delivery on the same day and only pay the $5 DwellSocial Fee once.View menu + order: <a href="https://dwell.social/3RQKSse" target="_blank" rel="nofollow noopener">https://dwell.social/3RQKSse</a>

Local Event: Wake up to donuts on your doorstep from Do-Rite! Order by 10pm Friday.

Wake up to donuts on your doorstep from...

Do-Rite Donuts is coming to you on Saturday, May 23rd! Enjoy a wide variety of freshly baked artisanal donuts in unusual...

Wake up to donuts on your doorstep from Do-Rite! Order by 10pm Friday.

DuPage Event Center & Fairgrounds

Kick off the summer antiques show season on Saturday, June 6, 2026, 9 - 3, at the 4th Annual Fox Valley at the Fairgrounds Antiques Show in Wheaton, Illinois. Dealers from 7 states will gather under one roof to present the best of Americana. This show was held for many decades at the Kane County Fairgrounds in St. Charles. The DuPage Event Center &amp; Fairgrounds is now their 'forever' home. Free parking. Good food and plenty of comfortable seating. ATM. Admission of $10 benefits historical preservation projects. Under 15 free.
All indoors.&nbsp;Free parking. Good food &amp; plenty of comfortable seating. ATM. 



Produced by:Chicago Suburban Antiques Dealers Association

Local Event: Fox Valley at the Fairgrounds Antiques Show

Cook County

Winnetka-Glencoe

Fox Valley at the Fairgrounds Antiques Show

Kick off the summer antiques show season on Saturday, June 6, 2026, 9 - 3, at the 4th Annual Fox Valley at the Fairgrounds...

Nichols Concert Hall

Chicago’s premier Jewish community choir, Kol Zimrah, joined by esteemed cantors, presents an extra-special annual benefit performance this year, as we celebrate our 30th anniversary!&nbsp; The concert will feature a program of eclectic favorites and contemporary works with a mix of old favorites and new selections from both traditional and modern composers, under conductor and music director Cantor Pavel Roytman.Kol Zimrah has much to celebrate from the last 30 years - and much to anticipate for our next 30!&nbsp; Be sure to join us for our benefit concert and support our ongoing mission to enrich and engage concert audiences, and build bridges with communities.Tickets: $40. Digital ads and sponsorship opportunities available.<figure><img src="https://cdn20.patchcdn.com/users/27266638/20260429/125911/image___29125910230.jpg" id="image.png" data-image="image.png"></figure>

Local Event: Kol Zimrah: 30 Years and Growing 2026 Benefit Concert

Deerfield

Kol Zimrah: 30 Years and Growing 2026 Benefit...

Chicago’s premier Jewish community choir, Kol Zimrah, joined by esteemed cantors, presents an extra-special annual benefit...

Kol Zimrah: 30 Years and Growing 2026 Benefit Concert

Tamarisk NorthShore

<h1>Legends, Lunch &amp; Sports Talk</h1>

<h3>Behind the Headlines: A Father’s Day Appreciation Event</h3>
<h3>Wednesday, June 10 | 11:30 a.m.–1 p.m.</h3>
Join us for a Father’s Day appreciation event featuring a winning lineup of Chicago sports stories and fast-paced trivia with veteran sportswriter Ed Sherman, paired with ballpark favorite eats prepared by Chef Laura. Drawing from his years covering the city’s biggest teams, Ed brings the play-by-play and insider stories sports fans won’t want to miss.
This event is free and open to the public, but an RSVP is requested by Monday, June 1.
<h3>RSVP by filling out the form on our website or call <a href="tel:847-597-8772">847-597-8772</a>.</h3>

Local Event: Legends, Lunch & Sports Talk | Behind the Headlines: A Father’s Day Appreciation Event

Legends, Lunch & Sports Talk | Behind the...

Legends, Lunch & Sports Talk

Behind the Headlines: A Father’s Day Appreciation Event
Wednesday, June 10 | 11:30 a.m.–1...

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Join us for The Memory Keepers, an evening featuring Holocaust authors published by <a href="https://amsterdampublishers.com/" rel="nofollow noopener" target="_blank">Amsterdam Publishers</a>, one of the world’s leading publishers of Holocaust memoirs. These writers – children and grandchildren of Holocaust survivors – carry forward their families’ histories with care and responsibility. Co-hosted by <a href="https://www.3gchicago.com/" rel="nofollow noopener" target="_blank">3G Chicago</a> and the <a href="https://ajanow.org/" rel="nofollow noopener" target="_blank">American Jewish Alliance</a>, this program brings together the voices that preserve these stories and the community committed to ensuring they endure. Together, they explore what it means to inherit memory and the responsibility to keep it alive for future generations.

Local Event: The Memory Keepers: An Evening with Holocaust Memoir Authors

The Memory Keepers: An Evening with Holocaust...

Join us for The Memory Keepers, an evening featuring Holocaust authors published by Amsterdam Publishers, one of the world’s...

The Memory Keepers: An Evening with Holocaust Memoir Authors

Chicago Executive Airport

<h2>Our Event Takes Off This June</h2>
<h5>Race Date: Saturday, June 27, 2026 at 8:00 AM</h5>
Join us for a 5K Run, 1 Mile Walk and Kids Dash on the main runway and taxiways at Chicago Executive Airport in Wheeling, Illinois. The 5K course is USATF Certified, and chip timed. Hang out after your event for podium awards, music, food, giveaways and kids activities. Plus keep an eye out for princess and superhero guest appearances through the morning!
Strollers and wagons are welcome. No pets are allowed. 
<h6>In case of inclement weather, a cancellation call will be made by 8:30AM on event day. This is a fundraising event with proceeds benefiting local aviation scholarships. As a result, no refunds will be issued, and the event will not be rescheduled.</h6>
<h6>Thank you for your support!</h6>

Local Event: Run the Runway at Chicago Executive Airport 

Wheeling

Run the Runway at Chicago Executive Airport 

Our Event Takes Off This June
Race Date: Saturday, June 27, 2026 at 8:00 AM
Join us for a 5K Run, 1 Mile Walk and Kids Dash on...

Eric DeGrechie

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Vernon Hills

Glenview

Arlington Heights

Amie Schaenzer

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Looking for a welcoming community in Highland Park? 

At Trinity Episcopal Church, we believe church is more than just a Sunday service — it’s a place to grow, connect, serve, and belong. Whether you’re searching for spiritual connection, meaningful friendships, family activities, or simply a peaceful place to reflect, Trinity welcomes everyone with open doors and open hearts. What you’ll find at Trinity: • Inspiring worship services • Community outreach and volunteer opportunities • Young Adult &amp; Adult gatherings • Seasonal events, concerts, and fellowship activities • A warm, inclusive community for individuals and families Located in the heart of Highland Park, Trinity Episcopal Church has long been a place where faith, compassion, and community come together. We invite you to visit, say hello, and experience the welcoming spirit of Trinity for yourself.

At Trinity Episcopal Church, we believe church is more than just a Sunday service — it’s a place to grow, connect, serve, and belong. Whether you...

Carmen Nedelcu Real Estate

I’m Carmen Nedelcu, and for 25 years I’ve helped buyers and sellers across Chicago’s North Shore navigate real estate with confidence and clarity. As a long-time local resident, I know Deerfield, Bannockburn, Riverwoods, and the surrounding communities firsthand—the neighborhoods, schools, market patterns, and subtle differences that truly impact value. Over the course of my career, I’ve closed more than $60 million in residential sales, guiding families, professionals, investors, and relocating clients through every type of market. What sets me apart is personal involvement and accountability. When you work with me, you work directly with me. I manage every detail—from pricing strategy and marketing to negotiations, inspections, and closing coordination—ensuring nothing is overlooked. I believe in honest advice, data-driven pricing, and proactive communication so you always understand your options and feel confident in your decisions. I specialize in residential homes, first-time buyers, move-up properties, downsizing transitions, and luxury estates. Operating under RE/MAX Top Performers, I combine the strength of a leading brokerage with a boutique, hands-on approach. My business is built on referrals and repeat clients because I treat every transaction with care, discretion, and local expertise. Real estate is not just about closing deals—it’s about helping you make the right move in the right community.

I’m Carmen Nedelcu, and for 25 years I’ve helped buyers and sellers across Chicago’s North Shore navigate real estate with confidence and clarity....

A. D. Bush Concrete

Whether you’re planning a new driveway, patio, garage floor, sidewalk, stairs, or another custom concrete project, A. D. Bush Concrete is ready to bring your vision to life. From small residential upgrades to larger projects, we’re committed to delivering quality craftsmanship that enhances both the appearance and value of your property. With over 55 years of hands-on experience in the concrete industry, we bring trusted knowledge, proven techniques, and attention to detail to every job. Our team works closely with you from start to finish to ensure your project is completed efficiently, professionally, and with as little disruption as possible. We take pride in making the entire process smooth and stress-free. Whether you’re looking for a clean, classic broom finish, decorative exposed aggregate, or a custom combination to create a unique look, we have the skill set and expertise to deliver outstanding results that stand the test of time. If you’re considering a concrete project, don’t wait to get started. Our schedule fills up quickly once the season gets underway. Contact A. D. Bush Concrete today to secure your spot and let’s turn your project into reality. Phone - 847-564-3295 Email - Bushconcrete@sbcglobal.net

Whether you’re planning a new driveway, patio, garage floor, sidewalk, stairs, or another custom concrete project, A. D. Bush Concrete is ready to...

Jet's Pizza

Jet’s Pizza is officially open in Wheeling, and we are excited to be serving the community! Known for our famous Detroit-Style Deep Dish Pizza, Jet’s Pizza delivers bold flavors, high-quality ingredients, and generous portions in every bite. Our menu features more than just pizza—enjoy crispy wings, fresh salads, cheesy bread, calzones, and more. Whether you like it classic or loaded with toppings, Jet’s Pizza offers customizable options to satisfy every craving. We’re proud to use premium ingredients, including our signature sauce and dough made fresh daily. Experience why Jet’s Pizza has become a favorite across the country. Perfect for family dinners, game nights, lunch breaks, or catering your next event—Jet’s Pizza is your new go-to spot for great food and great service. We look forward to welcoming you and becoming a part of the neighborhood. Stop by, order online, or call in—delicious pizza is just a slice away!

Jet’s Pizza is officially open in Wheeling, and we are excited to be serving the community! Known for our famous Detroit-Style Deep Dish Pizza, Jet...

America's #1 Luxury Pet Resort is Now Open in Deerfield.

K9 Resorts Luxury Pet Hotel Deerfield

Dog parents, rejoice: Chicagoland’s canine community has a new favorite place to stay and play. K9 Resorts Luxury Pet Hotel recently opened its first Illinois location in Deerfield, bringing award-winning pet care and resort-style amenities to the North Shore. With a 20-year track record of excellence and locations in 28 states and growing, K9 Resorts has earned its reputation as the most awarded pet care brand in the country. Designed with dogs (and their humans) in mind, K9 Resorts combines comfort, cleanliness, and professionalism to create a one-of-a-kind experience. Whether you're heading out of town or just need reliable weekday daycare, you’ll find peace of mind knowing your pet is cared for like family. The K9 Experience includes: • Luxury dog boarding and daycare, 365 days a year • Spacious, cage-free suites with premium beds • Indoor and outdoor play yards for safe, supervised fun • Hospital-grade cleaning protocols • A professionally trained staff that treats every guest like their own • Five-star customer service from start to finish Every detail of the Deerfield resort is tailored to create a stress-free, tail-wagging environment for your pet. No cages. No chaos. Just happy dogs and happy dog parents. Tours are available, and first-time guests are always welcome. To learn more or book a stay, visit k9resorts.com.

Dog parents, rejoice: Chicagoland’s canine community has a new favorite place to stay and play. K9 Resorts Luxury Pet Hotel recently opened its...

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Highland Park, IL|Local Event

Highland Park Wine Stroll

Event Details

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