# Events & Things To Do In Highwood, IL This Weekend | May 22-24, 2026| AllEvents

- **Subtitle**: Highwood, Illinois is a city full of experiences, activities and events. Explore some of the best things to do in Highwood, Illinois this weekend and make your Friday, Saturday and Sunday full of fun and excitement.
- **Category**: Weekend
- **Display Name**: Events this weekend
- **Type**: time_filter

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- **Followers**: 20.7k+
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## About

Weekends become special if you know how to make the most out of it. There are a lot of fun things to do and events in [CITY] this weekend for you to explore.

Make your weekends memorable. Check out all upcoming weekend events in [CITY].

## Weekend Events in Highwood

- **Event Name**: Kevin Purcell & the Root Doctors play Toadstool Pub
  - **Description**: Kevin Purcell and his all star band The Root Doctors!
  - **Interested Audience**:
    - Count: 49
  - **Date**: Fri May 22 2026 at 08:00 pm (-05:00)
  - **Event URL**: https://allevents.in/highwood/kevin-purcell-and-the-root-doctors-play-toadstool-pub/200030042217624
  - **Venue**: The Toadstool Pub
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy9hZWY2YjBjZGRmNTA1OTYyY2U2M2MyYmFjNGRmZDgzZWVlNjkyZWE4MDI0ZWM2OTc1MTlmMzNmY2UzNjJkYzFhLXJpbWctdzEyMDAtaDg1My1kYzA0MDMwMy1nbWlyP3Y9MTc3ODQzODk2Mw.avif
  - **Categories**: music, entertainment
- **Event Name**: Victor Brown Band at Toadstool Pub in Highwood
  - **Description**: Jam band VBB is unleashing deep grooves, extended jams and serious musical chemistry May 24 at Toadstool Pub in Highwood. No cover. Just pure sonic joy.

🎶 The party hits outside in the backlot.

#highwood #supportlocal #localbusiness #highwoodstrong #chi
  - **Interested Audience**:
    - Count: 59
  - **Date**: Sun May 24 2026 at 03:00 pm (-05:00)
  - **Event URL**: https://allevents.in/highwood/victor-brown-band-at-toadstool-pub-in-highwood/200029977089840
  - **Venue**: The Toadstool Pub
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  - **Categories**: entertainment, music, parties, live-music
- **Event Name**: Porcupine Avalanche at 28 Mile Distilling Co.
  - **Description**: Happy Hour just got louder 🎸🍻
Porcupine Avalanche returns to at 28 Mile Distilling Co. for a special 4:00 – 6:30 PM matinee/happy hour show.
Iconic venue, great food and drinks, and a whole lot of rock — what else do you need?  Hope to see you there!
  - **Interested Audience**:
    - Count: 13
  - **Date**: Sat May 23 2026 at 04:00 pm – Sat May 23 2026 at 06:30 pm (-05:00)
  - **Event URL**: https://allevents.in/highwood/porcupine-avalanche-at-28-mile-distilling-co/200030052871855
  - **Venue**: 28 Mile Distilling Co.
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- **Event Name**: Dave & Dave Acoustic Show at 28 Mile, Highwood. 8p
  - **Description**: Dave & Dave of Hi Infidelity perform acoustically.
  - **Interested Audience**:
    - Count: 25
  - **Date**: Sat May 23 2026 at 08:00 pm (-05:00)
  - **Event URL**: https://allevents.in/highwood/dave-and-dave-acoustic-show-at-28-mile-highwood-8p/200030052872408
  - **Venue**: 28 Mile Distilling Co.
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9jOTE2MzQzYjYyOTA4MTc1MzkxN2Q1YzM2NWZmMGVjYjk4N2E4MGIyNzBmYTIwMDk3NWNkYTEyNDE0YTRhYTllLXJpbWctdzEyMDAtaDgwMC1kYzA0MDQwMy1nbWlyP3Y9MTc3ODc3MTEwNQ.avif
- **Event Name**: 2026 Fallen Hero Memorial Day Weekend Fort Sheridan
  - **Description**: Join us Saturday May 23 at 9am to place a Fallen Hero Planter gravesite at For Sheridan National Cemetery.About this EventPlease join us this Saturday May 23 at 9am at Fort Sheridan National Cemetery as we place live Fall
  - **Date**: Sat May 23 2026 at 09:00 am – Sat May 23 2026 at 09:30 am (-05:00)
  - **Event URL**: https://allevents.in/highwood/2026-fallen-hero-memorial-day-weekend-fort-sheridan/100001989823720312
  - **Venue**: Ft  Sheridan  Cemetery
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  - **Price**: Free
  - **Categories**: Nonprofit

## Trending Events in Highwood

- **Event Name**: Great Highwood Pumpkin Festival
  - **Description**: 🎃✨The Great Highwood Pumpkin Fest Returns October 1–4, 2026!
Highwood’s favorite fall tradition is back for another unforgettable weekend of pumpkins, community spirit, and festive fun. The celebration kicks off on Thursday, October 1, with Community Nigh
  - **Venue**: 111 North Ave, Highwood, IL 60040-1521, United States
  - **Banner**: https://cdn-az.allevents.in/events5/banners/1e4b4db00a51dc5718e490de7cc055c4843b7061f865b6ed900c85059867dee3-rimg-w800-h534-dc0f1a47-gmir?v=1777431965
- **Event Name**: 🧄 Garlic Fest 2026 with music by A Tribute to Old Blue Eyes, sponsored by Scotty's on Sheridan
  - **Description**: Highwood’s beloved Garlic Fest will return in 2026 for another stinking good time! Thank you to Scotty's on Sheridan for sponsoring the live music performance! This annual celebration always brings big flavor, great energy, and plenty of garlic‑themed fun
  - **Venue**: 111 North Ave, Highwood, IL 60040-1521, United States
  - **Banner**: https://cdn-az.allevents.in/events1/banners/844a101e46420b09b66b7c73632cddb5e2de957d79823f3bd1a2293e044cbad2-rimg-w800-h533-dcd7f2fe-gmir?v=1778783713
- **Event Name**: Highwood Days Carnival & Taste of Highwood🎡
  - **Description**: 🎡Highwood Days & Taste of Highwood are coming together for an unforgettable three‑day summer celebration!

Get ready for a weekend filled with everything you love about summertime in Highwood. The long‑standing Highwood Days Carnival returns with clas
  - **Venue**: 111 North Ave, Highwood, IL 60040-1521, United States
  - **Banner**: https://cdn-az.allevents.in/events8/banners/7761d10117c71ebc7e7f71bf34844416f0d8c5665711f4b59369bf542939f264-rimg-w1200-h800-dceef1f7-gmir?v=1778976983
- **Event Name**: 🍅 Bloody Mary Fest
  - **Description**: Celebrate Highwood is gearing up for another unforgettable Bloody Mary Fest - a day filled with bold flavors, great music, community spirit, and plenty of creative twists on the classic cocktail. This beloved summer tradition brings together families, fri
  - **Venue**: 111 North Ave, Highwood, IL 60040-1521, United States
  - **Banner**: https://cdn-az.allevents.in/events7/banners/553eb7d755ae38b038f93854d8b5af27b093d68f8235ef1018fb9bf2d2771958-rimg-w800-h640-dcaaa9ab-gmir?v=1778952445
- **Event Name**: Highwood Evening Gourmet Market with music by Rollover
  - **Description**: Join us at the Evening Gourmet Market led by Rollover Band from 6-9 PM! This band blends roots rock with soulful Chicago blues for a high-energy, masterful performance that captivates every crowd.

There’s nothing quite like summer evenings in Highwood, a
  - **Venue**: 111 Highwood Ave, Highwood, IL, United States, Illinois 60040
  - **Banner**: https://cdn-az.allevents.in/events10/banners/07f64101c04f78e77ff6a31d3f0c124636fbad8433b902759f9cf67a3beec970-rimg-w1200-h899-dca9bfe0-gmir?v=1779042006
- **Event Name**: Highwood Evening Gourmet Market and Pride in the Park!🏳️‍🌈 Music by DJ Versage
  - **Description**: Get ready to celebrate love, community, and local flavor! It’s an evening dedicated to inclusivity and vibrant energy, set against the backdrop of our bustling community market. Jam the night away with DJ Versage, a high energy DJ who is as fun to watch a
  - **Venue**: 111 North Ave, Highwood, IL 60040-1521, United States
- **Event Name**: Kick-Off to Summer Carnival 🎪
  - **Description**: The community is invited to come out and mark the beginning of summer at this festive carnival with rides, games, and food. Families are invited to celebrate with discounted unlimited ride wristbands.

From carnival lights and festive energy to mouthwater
  - **Venue**: 406 Sheridan Rd, Highwood, IL 60040-1309, United States
  - **Banner**: https://cdn-az.allevents.in/events9/banners/cc209eb95b7c19521e4411c3969bc8bc7e359a17d8656056ef7c464d8bc1fe4b-rimg-w1200-h675-dc1a3246-gmir?v=1778723520
- **Event Name**: Highwood Evening Gourmet Market with music by Stevie Craig Band, sponsored by Bella Via
  - **Description**: Enjoy the soft jazz of Stevie Craig’s tunes, bringing his electric guitar and stellar singing to the iconic first night of celebration in Highwood’s Everts Park from 6-9 PM. A special thanks to Bella Via for sponsoring this live musical performance. 

The
  - **Venue**: 111 Highwood Ave, Highwood, IL, United States, Illinois 60040
  - **Banner**: https://cdn-az.allevents.in/events10/banners/4ca873537023d24010c6b581ccde8da6a0526a6f4c95012542aa432c9b668d43-rimg-w1200-h899-dca9bfe0-gmir?v=1778959613
- **Event Name**: Highwood Historical Cocktail Tour 2026
  - **Description**: See what all the "Buzz" is about as you experience the Highwood Historical Cocktail Tour.About this EventJoin tour guide, Bruce "Buzz" Bertucci, for the kick-off of Highwood Historical Cocktail Tours. Learn the hidden sec
  - **Venue**: Everts Park
  - **Banner**: https://cdn-az.allevents.in/events3/banners/de0acc9e16c77e3d7dc91f78fc096d1e959a8319a912d1455460063fa39fe76c-rimg-w1200-h900-dc778995-gmir.jpg?v=1779201124

## Browse Weekend Events by Date

- [Weekend Events Today in Highwood](https://allevents.in/highwood/this-weekend--today)
- [Weekend Events This Weekend in Highwood](https://allevents.in/highwood/this-weekend--this-weekend)
- [Weekend Events in May in Highwood](https://allevents.in/highwood/this-weekend--may)
- [Weekend Events in June in Highwood](https://allevents.in/highwood/this-weekend--june)

## FAQs

- **Q**: What are the top Weekend events in Highwood?
  - **A:** Kevin Purcell & the Root Doctors play Toadstool Pub (Fri May 22 2026 at 08:00 pm at The Toadstool Pub), Victor Brown Band at Toadstool Pub in Highwood (Sun May 24 2026 at 03:00 pm at The Toadstool Pub), Porcupine Avalanche at 28 Mile Distilling Co. (Sat May 23 2026 at 04:00 pm at 28 Mile Distilling Co.), Dave & Dave Acoustic Show at 28 Mile, Highwood. 8p (Sat May 23 2026 at 08:00 pm at 28 Mile Distilling Co.), 2026 Fallen Hero Memorial Day Weekend Fort Sheridan (Sat May 23 2026 at 09:00 am at Ft  Sheridan  Cemetery).
- **Q**: What are the top free Weekend events in Highwood?
  - **A:** 2026 Fallen Hero Memorial Day Weekend Fort Sheridan (Sat May 23 2026 at 09:00 am at Ft  Sheridan  Cemetery).
- **Q**: What Weekend events are happening in Highwood this weekend May 22–24, 2026?
  - **A:** Kevin Purcell & the Root Doctors play Toadstool Pub (Fri May 22 2026 at 08:00 pm at The Toadstool Pub), Victor Brown Band at Toadstool Pub in Highwood (Sun May 24 2026 at 03:00 pm at The Toadstool Pub), Porcupine Avalanche at 28 Mile Distilling Co. (Sat May 23 2026 at 04:00 pm at 28 Mile Distilling Co.), Dave & Dave Acoustic Show at 28 Mile, Highwood. 8p (Sat May 23 2026 at 08:00 pm at 28 Mile Distilling Co.), 2026 Fallen Hero Memorial Day Weekend Fort Sheridan (Sat May 23 2026 at 09:00 am at Ft  Sheridan  Cemetery).
- **Q**: What Weekend events are happening in Highwood in May 2026?
  - **A:** Kevin Purcell & the Root Doctors play Toadstool Pub (Fri May 22 2026 at 08:00 pm at The Toadstool Pub), Victor Brown Band at Toadstool Pub in Highwood (Sun May 24 2026 at 03:00 pm at The Toadstool Pub), Porcupine Avalanche at 28 Mile Distilling Co. (Sat May 23 2026 at 04:00 pm at 28 Mile Distilling Co.), Dave & Dave Acoustic Show at 28 Mile, Highwood. 8p (Sat May 23 2026 at 08:00 pm at 28 Mile Distilling Co.), 2026 Fallen Hero Memorial Day Weekend Fort Sheridan (Sat May 23 2026 at 09:00 am at Ft  Sheridan  Cemetery).
- **Q**: How can I find Weekend events in Highwood?
  - **A:** You can discover upcoming Weekend events in Highwood on AllEvents.in. Browse by date, venue, or price to find events that match your interests.
- **Q**: How do I buy tickets for Weekend events in Highwood?
  - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets.
- **Q**: What are the popular venues for Weekend events in Highwood?
  - **A:** Some popular venues hosting Weekend events in Highwood include The Toadstool Pub, 28 Mile Distilling Co., Ft  Sheridan  Cemetery.
- **Q**: Who are the top organizers for Weekend events in Highwood?
  - **A:** Popular organizers hosting Weekend events in Highwood include Kevin Purcell & the Root Doctors, Victor Brown Band, Porcupine Avalanche.
- **Q**: Are there any online Weekend events available?
  - **A:** Yes, many Weekend events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere.
- **Q**: How can I get notified about new Weekend events in Highwood?
  - **A:** Follow the Weekend category on AllEvents.in to get notified when new Weekend events are listed in Highwood.

## Category Banner

- **Banner Image**: https://cdn2.allevents.in/transup/01/bac113436441a783feaca7074943a8/this-weekend.webp

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