Highwood Library & Community Center

Highwood IL

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Art Workshop for Adults: Knitting • Taller de Arte para Adultos: Tejido Tradicional

Begyle Brewing

Punk'd: Mayfestiversary 2026

Highland Park Public Library - Brenner Room

Discussions with Ben

Christ Church Lake Forest

Join bestselling author and cultural commentator Andy Crouch for an evening exploring what it means to live faithfully and wisely in a technology-shaped world. Drawing from his acclaimed work on faith, culture, and technology, Andy will offer practical and hopeful insight for individuals, parents, and families seeking a more intentional way of life in the digital age.

Local Event: Pursuing A Tech-Wise Life With Andy Crouch

Lake County

Lake Forest-Lake Bluff

Illinois

Pursuing A Tech-Wise Life With Andy Crouch

Join bestselling author and cultural commentator Andy Crouch for an evening exploring what it means to live faithfully and...

Highwood, IL Calendar

Committee of the Whole

Council Meeting

Celebrate Highwood’s Wednesday Evening Gourmet Market brings together great food, community spirit, and a lively mix of live music all season long. Guests can explore local flavors while enjoying performances from a rotating lineup of regional favorites. The atmosphere is upbeat and welcoming, with bands and DJs that keep the energy high throughout the evening. This year’s lineup features acts such as The Vibe Cruisers, Rollover Band, Roger Black Band, Red Funk Band, DJ Versace, and more, creating a vibrant soundtrack for one of Highwood’s most popular weekly traditions.

Local Event: Celebrate Highwood – Wednesday Evening Gourmet Market Music Lineup

Highwood

Celebrate Highwood – Wednesday Evening Gourmet...

Celebrate Highwood’s Wednesday Evening Gourmet Market brings together great food, community spirit, and a lively mix of live...

Celebrate Highwood – Wednesday Evening Gourmet Market Music Lineup

Highland Park Public Library

Microsoft Word Basics

Evening Gourmet Market

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...

Ragdale, the nationally acclaimed artists’ residency program, located on the former Arts and Crafts country estate of architect Howard Van Doren Shaw, offers tours of the historic Ragdale House. Participants will learn about the Shaw family history and the celebrated artist in residence program. Visitors can experience the seven-acre site which includes three historic homes, several artist studios, gardens and vistas of the 50-acres Shaw Prairie. The Ragdale House and the Barn House, originally built in 1897, are both listed on the National Register of Historic Places. Tour donations help to support the mission of Ragdale.
ADMISSION: $15/person and online reservations must be made in advance

Local Event: Public Tour of the Historic Ragdale Campus

Public Tour of the Historic Ragdale Campus

Ragdale, the nationally acclaimed artists’ residency program, located on the former Arts and Crafts country estate of architect...

Celebrate Highwood invites the public “show their pride on the North Side” as they host Pride in the Park, a celebration of love and community, on Wednesday, June 17 from 4:30 - 9 PM. This new theme night during the beloved weekly Evening Gourmet Market will focus on family-friendly inclusivity, loaded with interactive art, games, and live entertainment by Highwood’s own DJ Versage, who’s high energy is as fun to watch as they are to listen to, playing hits for the whole family. For those looking to leave a lasting mark, Pride in the Park will feature an interactive mural installation, courtesy of The Art Center Highland Park. The ‘Find your Piece of the Puzzle’ community mural invites attendees to paint and collaborate on a puzzle piece that will be transformed into next year’s annual Pride in the Park poster. A Celebrate Highwood ‘Pride Rocks Garden’ painting station hosted by the North Shore Civic Club will offer guests the opportunity to paint custom rocks to be displayed in the community. Free activity tables will be onsite, as well as giant yard games to play, including Connect 4, Jenga, and Twister.

Local Event: Pride in the Park

Pride in the Park

Celebrate Highwood invites the public “show their pride on the North Side” as they host Pride in the Park, a celebration of...

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

Highland Park

Highland Park Wine Stroll

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

Rachel Barnes

Chicago Metropolitan Area

Eric DeGrechie

Deerfield

Northbrook

Vernon Hills

Buffalo Grove

Glenview

Amie Schaenzer

Libertyville

Wilmette-Kenilworth

Lake

Looking for a welcoming community in Highland Park? 

Trinity Episcopal Church

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...

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Events and Things to Do in Highwood, IL

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Please confirm event details with the organizers before attending

Saturday, May 23

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Wednesday, June 3

Saturday, June 6

Saturday, June 13

Wednesday, June 17

Thursday, June 18

Trinity Episcopal Church