Port Clinton Square

The City of Highland Park is thrilled to announce an eclectic line-up of coordinated entertainment and cuisine as part of the 2026 Downtown Concerts at Port Clinton series. Select Fridays, July 10 through September 25 at Port Clinton Square in Downtown Highland Park, the public is invited to take a trip around the world - without ever leaving Highland Park. Attendees will partake in global cuisine from a different onsite local Highland Park restaurant each week while enjoying accompanying world music and entertainment. No passport necessary.
Over the course of ten Friday evenings, attendees are encouraged to bring lawn chairs to Port Clinton Square and start their summer weekends with free live music for the entire family. Concerts will generally run from 6 PM - 8 PM. Please note there will be no concerts July 24 or August 28, and the July 10 concert will take place from 5 PM - 7 PM. The season finale on September 25 will be held from 4 PM – 8 PM and feature the return of the ever-popular Scarecrow Trail through Downtown Highland Park. Over one dozen Downtown businesses will decorate seasonal scarecrows in front of their shops, creating a fun and festive Scarecrow Trail. Attendees will be able to vote “best in show, with the winner being announced during Stews &amp; Brews on October 10.
Tamales will turn up the heat in Downtown Highland Park with their beloved Mexican cuisine. Salsa dancers will groove to the tunes of the Cecy Santana Trio and Orquesta Alta Vida in celebration of Mexican Independence Day.

Local Event: Port Clinton Concert Series: Sabor De Libertad

Lake County

Highland Park

Illinois

Port Clinton Concert Series: Sabor De Libertad

The City of Highland Park is thrilled to announce an eclectic line-up of coordinated entertainment and cuisine as part of the...

The City of Highland Park will celebrate the start of the fall season with its third annual Scarecrow Fest and the grand finale of the 2026 Downtown Concert Series at Port Clinton Square and throughout downtown on Sept. 25 from 4-8 p.m.
Attendees can stroll through Highland Park’s Central Business District to discover more than two dozen uniquely decorated scarecrows displayed throughout participating downtown businesses and vote for the “Best in Show Scarecrow.”
The celebration continues at Port Clinton Square with family-friendly activities, live music, food and drinks, and fall-themed fun. Activities include face painting, airbrush tattoos, pumpkin crafts, Wizard of Oz characters, including Dorothy and Glinda, and larger-than-life scarecrow puppets.
Live performances will include Miss Jamie’s Farm from 4-4:30 p.m., Istvan &amp; His Imaginary Band from 4:45-5:15 p.m., Ben Tatar &amp; The Tatar Tots from 5:30-6:30 p.m., and Taylor &amp; Mane from 6:30-8 p.m.
Local food and drink vendors will be onsite, with beverages available for attendees 21 and older. Guests are encouraged to bring a lawn chair and enjoy an evening of fall festivities, live entertainment and community fun in downtown Highland Park. Don't miss this festive fall celebration in downtown Highland Park!

Local Event: Scarecrow Fest

Scarecrow Fest

The City of Highland Park will celebrate the start of the fall season with its third annual Scarecrow Fest and the grand finale...

The City of Highland Park is thrilled to announce an eclectic line-up of coordinated entertainment and cuisine as part of the 2026 Downtown Concerts at Port Clinton series. Select Fridays, July 10 through September 25 at Port Clinton Square in Downtown Highland Park, the public is invited to take a trip around the world - without ever leaving Highland Park. Attendees will partake in global cuisine from a different onsite local Highland Park restaurant each week while enjoying accompanying world music and entertainment. No passport necessary.
Over the course of ten Friday evenings, attendees are encouraged to bring lawn chairs to Port Clinton Square and start their summer weekends with free live music for the entire family. Concerts will generally run from 6 PM - 8 PM. Please note there will be no concerts July 24 or August 28, and the July 10 concert will take place from 5 PM - 7 PM. The season finale on September 25 will be held from 4 PM – 8 PM and feature the return of the ever-popular Scarecrow Trail through Downtown Highland Park. Over one dozen Downtown businesses will decorate seasonal scarecrows in front of their shops, creating a fun and festive Scarecrow Trail. Attendees will be able to vote “best in show, with the winner being announced during Stews &amp; Brews on October 10.
Commemorate fall with scarecrows, pumpkins, great food, live music, and family fun! The Downtown Concerts Season Finale features a line-up of family-friendly music and activities, seasonal decor, and a Scarecrow Trail through town to see over two dozen festive scarecrows, each uniquely decorated by local businesses, to cast a vote for “Best in Show.”

Local Event: Port Clinton Concert Series: Scarecrow Fest

Port Clinton Concert Series: Scarecrow Fest

Jens Jensen Park

The City of Highland Park will celebrate fall and all things Bavarian with Oktoberfest in Jens Jensen Park and along Dean Avenue in the Ravinia District on Sept. 26 from 4-8 p.m. This free, family-friendly event will feature traditional Oktoberfest activities, German-style music and entertainment, dancing, food, contests and more.
The event will feature live entertainment throughout the evening, including performances by Eidelweiss Chicago Bavarian Dancers from 4-4:15 p.m., Alpine Thunder from 4:15-5:45 p.m. and Icons of Country from 6-8 p.m. A stein-holding contest will take place from 5:30-6 p.m.
Attendees can enjoy a variety of interactive activities, including hammer-schlagen, axe throwing, a high striker, ring-o, cornhole and pretzel necklace making, along with other family-friendly entertainment.
Local vendors will offer a variety of German-inspired food and beverages, including soft pretzels, spaetzle, schnitzel, bratwurst, sauerkraut and more. Beer, wine, glühwein and apple cider will also be available.
Don’t miss this festive celebration of fall and all things Bavarian in the Ravinia District!

Local Event: Oktoberfest

Oktoberfest

The City of Highland Park will celebrate fall and all things Bavarian with Oktoberfest in Jens Jensen Park and along Dean...

Celebrate Highwood will host its 17th annual Great Highwood Pumpkin Festival throughout downtown Highwood on Oct. 2-4, 2026. The free, family-friendly festival will feature pumpkin carving, live music, carnival rides and games, trick-or-treating, children’s and pet costume contests, pumpkin pie eating contests, food and artisan vendors, seasonal installations and more.
The festival will begin with Community Pumpkin Carving on Oct. 1 from 4-9 p.m., followed by a full weekend of fall festivities. Highlights include the Great Pumpkin Wall Lighting at 7 p.m. Saturday, along with the Pet Costume Contest, Kids Costume Contest and Pumpkin Pie Eating Contest on Sunday.
Festival activities will take place throughout Highwood, including Highwood City Hall, Green Bay Avenue, Everts Park and the Highwood Metra Station Parking Lot, which will host a full carnival. Attendees can also enjoy two large pumpkin walls, community carving stations, Culver’s “Curdtoberfest” and Micro NASCAR Racing sponsored by Field’s Auto Group.
The 2026 festival will benefit SaLT (Service and Learning Together), a nonprofit supporting food-insecure families, academic tutoring, communities in crisis and service-learning initiatives.&nbsp;
Come celebrate the season, enjoy some fall fun and experience one of Highwood’s favorite annual traditions!&nbsp;

Local Event: Celebrate Highwood’s 17th Annual Great Highwood Pumpkin Festival

Highwood

Celebrate Highwood’s 17th Annual Great Highwood...

Celebrate Highwood will host its 17th annual Great Highwood Pumpkin Festival throughout downtown Highwood on Oct. 2-4, 2026....

Celebrate Highwood’s 17th Annual Great Highwood Pumpkin Festival

The City of Highland Park will welcome fall with the fifth annual Stews &amp; Brews on Oct. 10 from 4-9 p.m. at Port Clinton Square and along Central Avenue in downtown Highland Park. This free, all-ages event will feature comfort foods and beverages, live entertainment, fire pits and heat towers, children’s programming and the People’s Choice Competition for Favorite Stew and Brew.
Attendees can enjoy live entertainment throughout the evening, including DJ Madrid Perry from 4-5:15 p.m., 88 Keys Dueling Pianos from 5:15-6:45 p.m., DJ Madrid from 6:45-7:15 p.m. and Libido Funk Circus from 7:15-9 p.m.
New for 2026, children’s programming will be offered at Port Clinton Square from 4-6 p.m., including a performance by Mary Macaroni from 4-4:30 p.m., K-Pop Demon Hunters from 4-5 p.m. and free face painting and airbrush tattoos from 4-6 p.m.
Local vendors will offer a variety of comfort foods and beverages, including stews, soups, chili and more. Guests can also enjoy a selection of coffees and cocoas, craft beers, spiced wine, hot toddies, mulled ciders and other seasonal beverages.
Throughout the evening, attendees can vote for their favorite stew and brew in the People’s Choice Competition. Voting closes at 8 p.m., with winners announced at 8:30 p.m. Guests can also cozy up around fire pits and heat towers while enjoying an evening of food, drinks, music and fall fun.
Don’t miss this cozy fall celebration in downtown Highland Park!

Local Event: Stews & Brews

Stews & Brews

The City of Highland Park will welcome fall with the fifth annual Stews & Brews on Oct. 10 from 4-9 p.m. at Port Clinton Square...

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Rachel Barnes

Chicago Metropolitan Area

Eric DeGrechie

Deerfield

Cook County

Northbrook

Winnetka-Glencoe

Lake Forest-Lake Bluff

Glenview

Buffalo Grove

Vernon Hills

Wilmette-Kenilworth

Niles-Morton Grove

Amie Schaenzer

Libertyville

Sabor A Café Niles - Steakhouse & Live Music Venue

Celebrate the Jewish New Year Concert with Maxwell Street Klezmer Band!&nbsp;For this show, special guests musicians and singers will join the group on stage at Sabor a Café in Niles, for "Klezmer Night."

Discover a warm and inviting contemporary setting perfect for date night or a night out with friends and family. Enjoy your dinner before the show or during the performance. You can come for a sumptuous meal or just for drinks.


Klezmer, the traditional music of the Jews of the Shtetls of Eastern Europe, was brought to America by Jewish immigrants, where it merged with jazz in the early 1900s. From Yiddish folk and theater songs to rollicking dance music, Maxwell Street Klezmer Band has been reinventing the tradition since 1983 with warmth and humor.
Monthly Klezmer Night with Maxwell Street Klezmer Band!
Wednesday, September 23rd, 7:00 PM - 9:00 PM
Sabor a Café, 6873 N. Milwaukee in Niles&nbsp;No cover. Free parking.

About Maxwell Street Klezmer Band:&nbsp;
Founded in 1983 by Lori Lippitz, Maxwell Street Klezmer Band has played at Carnegie Hall, toured Europe, and provided the soundtrack for Chicagoland’s Jewish celebrations for over 4 decades. The band marked its 40th “Bandiversary” at The Old Town School of Folk Music in 2023. The group is releasing a new live album as well as an educational band book series in 2026.&nbsp; 
Reservations recommended: Go to&nbsp;<a href="https://saboracafeniles.com/" target="_blank" rel="nofollow noopener">saboracafeniles.com</a>&nbsp;to make reservations online.<a href="https://www.klezmerband.com/klezmer-night-at-sabor-a-cafe" target="_blank" rel="nofollow noopener">Learn more about Klezmer Night here.</a>

Local Event: Jewish New Year Concert with Maxwell Street Klezmer Band

Skokie

Jewish New Year Concert with Maxwell Street...

Celebrate the Jewish New Year Concert with Maxwell Street Klezmer Band! For this show, special guests musicians and singers...

Jewish New Year Concert with Maxwell Street Klezmer Band

Northmoor Country Club

The Ninth Annual Event for the GPF Foundation​ features a keynote appearance by Ryan Knutson​, Editor &amp; Co-Host of ​T​he Journal, the daily podcast from the Wall Street Journal​. ​Lake Forest's Larry Potash, WGN-TV, ​w​ill again be emcee. ​Funds raised support the GPF Foundation’s goal of “Saving Lives Through Awareness.”
Ryan Knutson is a co-host and senior news editor of “The Journal,” a daily podcast produced by the Wall Street Journal that explores the forces driving global events, markets and major companies. Previously he worked at PBS and ProPublica, building a reputation for sharp investigative reporting and clear, accessible storytelling. Just like the GPF Foundation, Ryan's work helps bring awareness and understanding about news and events that impact us all.
In addition to the cocktail party, seated meal and conviviality, guests at the Annual Event will also hear an update on GPF Foundation initiatives from Ross and Nancy Friedman, Board Chair and Director, respectively. Current activities include:

<ul><li>Continued progress on the Blind Spot, an educational video game that has moved into the third phase of development to explore commercial viability.</li><li>First-responder and health professional training and partnerships.</li><li>Development of a diagnostic scoring system for medical professionals.</li><li>On-going Harm Reduction training for at-risk communities.</li><li>The launch of an Associate Board made up of young adult volunteers to help spread awareness on harm reduction and the Foundation’s life-saving work. </li></ul>

Local Event: An Evening of Insight Promised at the GPF Foundation's Ninth Annual Event

An Evening of Insight Promised at the GPF...

The Ninth Annual Event for the GPF Foundation​ features a keynote appearance by Ryan Knutson​, Editor & Co-Host of ​T​he...

An Evening of Insight Promised at the GPF Foundation's Ninth Annual Event

Lake Forest College

Explore the power of artificial intelligence in everyday life—join Lake Forest College professors Dr. Benjamin Zeller and Dr. Rachel Whidden for the return of this highly-acclaimed community engagement series
Artificial Intelligence and Everyday Life: Understanding, Engaging, and Applying AI
Registration fee: $450 for the five-week series
Registration deadline: Thursday, October 8
Course times: Thursday evenings, 6-8:30 p.m.
Course dates: October 15, October 22, October 29, November 5, November 12
Artificial Intelligence is rapidly changing how we learn, work, create, communicate, and make decisions. Held at the historic Krebs Center for the Humanities, this five-week series offers an accessible introduction to AI while exploring the ethical, social, cultural, and philosophical questions it raises – through demonstrations, discussion, and real-world case studies designed to help participants become informed and thoughtful users of these emerging technologies. Each week will highlight a new topic and begin with a social reception featuring food and refreshments.
Both the educational content and social receptions will offer opportunities to build community, engage with College leadership, and learn more about ongoing campus initiatives.
Register for this course by clicking <a href="https://www.lakeforest.edu/community/lifelong-learning/ai-series-x86317" rel="nofollow noopener" target="_blank">HERE</a>.
Visit the Community Engagement website by clicking <a href="https://www.lakeforest.edu/community" rel="nofollow noopener" target="_blank">HERE</a>.
Registration is required to attend. Participants are encouraged to attend all sessions, but full attendance is not required.

Local Event: Lake Forest College Community Engagement Lifelong Learning Series: AI Course

Lake Forest College Community Engagement...

Explore the power of artificial intelligence in everyday life—join Lake Forest College professors Dr. Benjamin Zeller and Dr....

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Posting Activity

Port Clinton Concert Series: Sabor De Libertad

SEP

18

6:00 PM

Port Clinton Square, 600-601 Central Ave, Highland Park, IL

Scarecrow Fest

SEP

25

4:00 PM

Port Clinton Square, 600-601 Central Ave, Highland Park, IL

Port Clinton Concert Series: Scarecrow Fest

SEP

25

6:00 PM

Port Clinton Square, 600-601 Central Ave, Highland Park, IL

Oktoberfest

SEP

26

4:00 PM

Jens Jensen Park, 486 Roger Williams Ave, Highland Park, IL

Celebrate Highwood’s 17th Annual Great Highwood Pumpkin Festival

OCT

2

4:00 PM

Highwood, IL

Stews & Brews

OCT

10

4:00 PM

Port Clinton Square, 600-601 Central Ave, Highland Park, IL

Jewish New Year Concert with Maxwell Street Klezmer Band

An Evening of Insight Promised at the GPF Foundation's Ninth Annual Event

Lake Forest College Community Engagement Lifelong Learning Series: AI Course