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

Lake County

Highwood

Illinois

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

Port Clinton Square

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

Highland Park

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

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

Join Forester Athletics for Community &amp; Alumni Day, a celebration of our connection to the community and our alumni!
We invite alumni, families, community members, F.A.N. Club members, and Forester fans of all kinds to campus to cheer on Forester Athletics, enjoy food and drinks from local food trucks, and take part in family-friendly activities and giveaways. Come snap a photo with Boomer the Bear, show your Forester spirit, and shop for Lake Forest College merchandise!
Event Schedule includes:
11 a.m. | Men’s Soccer vs. Grinnell — Farwell Field 12 – 4p.m. | Food Truck Social — Tailgate Lot, South Campus 1 p.m. | Women’s Volleyball vs. Ripon — Sports &amp; Recreation Center 1:30 p.m. | Women’s Soccer vs. Grinnell — Farwell Field
Complimentary food truck meal tickets are available to the first 50 pre-registered Community Members, as well as all F.A.N. Club members and alumni of Men’s Soccer, Women’s Soccer, Men’s Golf, and Women’s Golf.
Please reach out to fanclub@lakeforest.edu with any questions. Go Foresters!

Local Event: Lake Forest College Community Engagement Event: Community Sports Day

Lake Forest College Community Engagement Event:...

Join Forester Athletics for Community & Alumni Day, a celebration of our connection to the community and our alumni!
We invite...

Lake Forest College Community Engagement Event: Community Sports Day

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

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

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

Lake Forest College Community Engagement Event: Community Sports Day

Lake Forest College Community Engagement Lifelong Learning Series: AI Course