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. 

Madame Zuzu’s

<a href="https://www.eventbrite.com/cc/live-comedy-at-madame-zuzus-3649459" rel="nofollow noopener" target="_blank">Tickets on Sale Now:</a> <a href="https://www.eventbrite.com/cc/live-comedy-at-madame-zuzus-3649459" rel="nofollow noopener" target="_blank">$20/per person $25 at door or day of show</a>
<h2>MAY HEADLINER: MIKE STRICKER (ZANIES | "BALL BUSTERS" GOLF ROASTS) with Michelle Krajecki!</h2>
Madame Zuzu’s is a local plant-based teashop in Highland Park, Illinois, owned and operated by musician Billy Corgan, founder of the grammy-winning Smashing Pumpkins, and fashion designer Chloe Mendel. Madame Zuzu’s combines insanely delicious plant-based foods, rare teas of the world, and an open source venue for the arts. Funnier by the Lake Comedy is one of Zuzu’s most popular events! Our shows are always PG-13!

Local Event: Live Stand-Up Comedy @ Madame Zuzu's

Live Stand-Up Comedy @ Madame Zuzu's

Tickets on Sale Now: $20/per person $25 at door or day of show
MAY HEADLINER: MIKE STRICKER (ZANIES | "BALL BUSTERS" GOLF...

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.

Stay in and enjoy standout meals from the city’s best local restaurants. DwellSocial brings your favorites straight to your door—order soon and treat yourself.
Sun, May 24: Prime Meats by Lettuce:	<a href="https://dwell.social/43jIrRt" rel="nofollow noopener" target="_blank">dwell.social/43jIrRt</a> Smoque BBQ:	<a href="https://dwell.social/42QfAEj" rel="nofollow noopener" target="_blank">dwell.social/42QfAEj</a> Sweet Mandy B's:	<a href="https://dwell.social/42N3Sdy" rel="nofollow noopener" target="_blank">dwell.social/42N3Sdy</a> Mon, May 25: Do-Rite Donuts:	<a href="https://dwell.social/4tXqdAs" rel="nofollow noopener" target="_blank">dwell.social/4tXqdAs</a> Honey Butter Fried Chicken:	<a href="https://dwell.social/4wFONs3" rel="nofollow noopener" target="_blank">dwell.social/4wFONs3</a> Joe's Seafood, Prime Steak, &amp; Stone Crab:	<a href="https://dwell.social/4tNvqui" rel="nofollow noopener" target="_blank">dwell.social/4tNvqui</a> Offset BBQ:	<a href="https://dwell.social/4tT5UUB" rel="nofollow noopener" target="_blank">dwell.social/4tT5UUB</a> Prince St. Pizza:	<a href="https://dwell.social/42Nojaf" rel="nofollow noopener" target="_blank">dwell.social/42Nojaf</a> Quartino:	<a href="https://dwell.social/4tHZjfz" rel="nofollow noopener" target="_blank">dwell.social/4tHZjfz</a>

Local Event: Celebrate Memorial Day with BBQ, Steaks, Seafood, Pizza, Italian & Sweet Treats Delivered!

Cook County

Evanston

Celebrate Memorial Day with BBQ, Steaks,...

Stay in and enjoy standout meals from the city’s best local restaurants. DwellSocial brings your favorites straight to your...

Celebrate Memorial Day with BBQ, Steaks, Seafood, Pizza, Italian & Sweet Treats Delivered!

The Art Center Highland Park

A unique 60-minute crystal bowl and voice experience with Marian McNair, followed by artistic exploration through color and form.Marian McNair, MATC, MFA, has been a sound therapist working with multiple crystal bowls for over 35 years and works with many organizations and individuals throughout the country, bringing the knowledge and science of sound with her intuitive skills and soothing, angelic voice. Prepare to immerse yourself in an extraordinary experience of Crystal Bowl Sound Meditation, guided by the renowned Marian McNair. Step into a haven of serenity as you find solace in your own personal space, enveloped by the ethereal melodies of crystal bowls and Marian's captivating voice. Prepare to be transported on a transformative journey of inner exploration. Marian’s unwavering dedication to assisting others on their personal journeys shines through her passion for vibrational sound healing. With her wealth of experience, Marian imparts her wisdom through yoga and sound meditation classes and imparts the art of playing crystal bowls to those who yearn to delve deeper into their spiritual awareness with this mesmerizing instrument. Embrace the moment of tranquility as you unfurl your yoga mat, snuggle into your cushion, or wrap yourself in a cozy blanket, fully surrendering to the enchanting soundscape that awaits. Immerse yourself in the soothing vibrations and allow them to gently dissolve your worries, inviting a profound sense of peace and harmony into your being. In the embrace of this serene ambiance, creativity may come knocking at your door. To inspire your artistic spirit, art supplies will be thoughtfully provided, inviting you to capture the essence of your experience through color and form.&nbsp;

Local Event: Crystal Bowl Sound Meditation

Crystal Bowl Sound Meditation

A unique 60-minute crystal bowl and voice experience with Marian McNair, followed by artistic exploration through color and...

Highland Park Community House

<a href="https://pilgrimplayers.org/" target="_blank" rel="nofollow noopener">Pilgrim Chamber Players</a> closes its 28th season with a tribute to Johannes Brahms. On Sunday, May 31st at 3 PM, BRAHMS' CELEBRATION will feature world-class chamber musicians performing Schumann’s&nbsp;romantic&nbsp;Fantasiestücke,&nbsp;Opus 73 for viola and piano, followed by&nbsp;Brahms’ passionate,&nbsp;bold&nbsp;Cello Sonata No. 2&nbsp;in F major.&nbsp; The program&nbsp;concludes with Brahms’&nbsp;ebullient&nbsp;String Sextet No 1 in B&nbsp;flat major.&nbsp;Cellist and&nbsp;Artistic Director <a href="https://stevenhonigberg.com/bio.htm" target="_blank" rel="nofollow noopener">Steven Honigberg</a> — who studied with the legendary cellist Leonard Rose, famed for his Brahms recordings — leads an exceptional ensemble including special guest&nbsp;violist&nbsp;<a href="https://www.juilliard.edu/music/faculty/appel-toby" target="_blank" rel="nofollow noopener">Toby Appel</a>&nbsp;as well as&nbsp;violist <a href="https://anthonydevroye.com/" target="_blank" rel="nofollow noopener">Anthony Devroye</a>;&nbsp;violinists&nbsp;<a href="https://www.chicagolyricoperaorchestra.com/john-macfarlane" target="_blank" rel="nofollow noopener">John</a> and <a href="https://athenaeumcenter.org/performers/karyn-macfarlane/" target="_blank" rel="nofollow noopener">Karyn Macfarlane</a>;&nbsp;cellist <a href="https://haddonkay.com/" target="_blank" rel="nofollow noopener">Haddon Kay</a>, and pianist <a href="https://martaaznavoorian.com/#" target="_blank" rel="nofollow noopener">Marta Aznavoorian</a>. Tickets&nbsp;for the <a href="https://www.highlandparkcommunityhouse.org/" target="_blank" rel="nofollow noopener">Highland Park Community House</a> concert&nbsp;are twenty dollars for adults, ten dollars for students, and include a post-concert reception.&nbsp;Reserve your seat at&nbsp;<a href="https://pilgrimplayers.org./?utm_source=hs_email&amp;utm_medium=email&amp;_hsenc=p2ANqtz-9G4zm7nuxa-c37_QVJV8qiOOO9I2CCq5NMR6THSjH_ybOcy39hgQq9lZ1PXXBS6cMi1GHZ" target="_blank" rel="nofollow noopener">pilgrimplayers.org.&nbsp;</a>

Local Event: Brahms' Celebration

Brahms' Celebration

Pilgrim Chamber Players closes its 28th season with a tribute to Johannes Brahms. On Sunday, May 31st at 3 PM, BRAHMS'...

111 North Ave

Celebrate Highwood is excited to announce its 2026 season of festivals and community events. The year begins with the Evening Gourmet Market (June 3–August 26), bringing weekly Wednesday nights of food, music, and more than 60 vendors to Everts Park. Summer officially kicks off with the Kick-off to Summer Carnival (June 5–7), followed by the fiery fun of Inferno Fest (June 24). July features Highwood Days &amp; the 2nd Annual Taste of Highwood (July 17–19), along with the community‑favorite Highwood 5K Run, Walk &amp; Stroll (July 18). Later in the month, Margarita Night (July 29) brings tropical energy and Jimmy Buffet–style entertainment. August highlights include Garlic Fest (August 12), celebrating creative sweet and savory garlic dishes, and Bloody Mary Fest (August 16), where mixologists showcase inventive tomato‑based cocktails. Over Labor Day weekend, Nashwood (September 4–6) transforms Downtown Highwood into a Nashville‑inspired music takeover. Fall brings the iconic Great Highwood Pumpkin Festival (October 2–4), the North Shore’s largest autumn celebration, and the year wraps up with the festive Elf Invasion Pub Crawl (December 5).

Local Event: Celebrate Highwood Announces 2026 Series of Family-Friendly Festivals and Events

Celebrate Highwood Announces 2026 Series of...

Celebrate Highwood is excited to announce its 2026 season of festivals and community events. The year begins with the Evening...

Celebrate Highwood Announces 2026 Series of Family-Friendly Festivals and Events

Eric DeGrechie

Deerfield

Northbrook

Winnetka-Glencoe

Lake Forest-Lake Bluff

Glenview

Buffalo Grove

Vernon Hills

Wilmette-Kenilworth

Niles-Morton Grove

Amie Schaenzer

Libertyville

Deerfield Italian Kitchen

Come hang out with like minded people and see some beautiful nature photography at our next Deerfield Green Drinks. &nbsp;The speaker is a local nature photographer, Lisa Musgrave. &nbsp;The presentation title is - Slow down and look close! &nbsp;Come see photos of critters found in our forest preserves!
Food and drinks available for purchase.

Local Event: Green Drinks - Come see nature photography!  Speaker - Lisa Musgrave

Green Drinks - Come see nature photography! ...

Come hang out with like minded people and see some beautiful nature photography at our next Deerfield Green Drinks.  The...

Green Drinks - Come see nature photography!  Speaker - Lisa Musgrave

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...

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...

North Shore School of Dance

For over 35 years, the North Shore School of Dance (NSSD) has been a leader in dance education and professional training. Our dedicated faculty provides high-quality instruction in a nurturing, disciplined, and inspiring environment. We strive to educate the mind, body, and soul—honoring the tradition of dance as an art form. At NSSD, we don’t just teach routines—we teach students how to dance. Our training builds confidence, discipline, and lifelong skills Classes are offered in ballet, pointe, modern, contemporary, jazz, hip-hop, lyrical, Pre-school dance, Mommy and me, and adult classes.

For over 35 years, the North Shore School of Dance (NSSD) has been a leader in dance education and professional training. Our dedicated faculty...

Nearby Communities

State Edition

National Edition

Highland Park|Local Event

Highland Park Wine Stroll

Event Details

More Upcoming Events

Debate without Hate

MAY

21

6:00 PM

Trinity Episcopal Church, 425 Laurel Ave, Highland Park, IL

Live Stand-Up Comedy @ Madame Zuzu's

MAY

22

7:30 PM

Madame Zuzu’s, 1876 1st St, Highland Park, IL

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

MAY

23

7:00 AM

Highland Park, IL

Celebrate Memorial Day with BBQ, Steaks, Seafood, Pizza, Italian & Sweet Treats Delivered!

MAY

24

10:00 AM

Evanston, IL

Crystal Bowl Sound Meditation

MAY

27

6:30 PM

The Art Center Highland Park, 1957 Sheridan Rd, Highland Park, IL

Brahms' Celebration

MAY

31

3:00 PM

Highland Park Community House, 1991 Sheridan Rd, Highland Park, IL

Celebrate Highwood Announces 2026 Series of Family-Friendly Festivals and Events

JUN

3

4:30 PM

Highland Park, IL

Green Drinks - Come see nature photography! Speaker - Lisa Musgrave

Debate without Hate

Trinity Episcopal Church

K9 Resorts Luxury Pet Hotel Deerfield

North Shore School of Dance