Make your life happening by enrolling to entertainment events in [CITY]. Find a partner through a salsa night or take your partner to live in concerts by upcoming bands in your town. Get high while playing Beer Pong in a pub crawl or attending stand-up comedy events in [CITY]. Shake your legs in the happy streets, zumba or dance workshops or go for a film screening in the nearby cafes or theaters.
Explore Entertainment Events in [CITY].
## Entertainment Events in Highwood - **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 - **Interested Audience**: - Count: 498 - **Date**: Wed Aug 12 2026 at 04:30 pm – Wed Aug 12 2026 at 09:00 pm (-05:00) - **Event URL**: https://allevents.in/highwood/garlic-fest-2026-with-music-by-a-tribute-to-old-blue-eyes-sponsored-by-scottys-on-sheridan/200029598152538 - **Venue**: 111 North Ave, Highwood, IL 60040-1521, United States - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy84NDRhMTAxZTQ2NDIwYjA5YjY2YjdjNzM2MzJjZGRiNWUyZGU5NTdkNzk4MjNmM2JkMWEyMjkzZTA0NGNiYWQyLXJpbWctdzgwMC1oNTMzLWRjZDdmMmZlLWdtaXI_dj0xNzc4NzgzNzEz.avif - **Categories**: festivals, music, live-music, art, entertainment - **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 - **Interested Audience**: - Count: 1609 - **Date**: Fri Jul 17 2026 at 05:00 pm – Sun Jul 19 2026 at 10:00 pm (-05:00) - **Event URL**: https://allevents.in/highwood/highwood-days-carnival-and-taste-of-highwood/200029532717109 - **Venue**: 111 North Ave, Highwood, IL 60040-1521, United States - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy83NzYxZDEwMTE3YzcxZWJjN2U3ZjcxYmYzNDg0NDQxNmYwZDhjNTY2NTcxMWY0YjU5MzY5YmY1NDI5MzlmMjY0LXJpbWctdzEyMDAtaDgwMC1kY2VlZjFmNy1nbWlyP3Y9MTc3NzEyNTE1Nw.avif - **Categories**: carnivals, festivals - **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 - **Interested Audience**: - Count: 362 - **Date**: Fri Jun 05 2026 at 05:00 pm – Sun Jun 07 2026 at 10:00 pm (-05:00) - **Event URL**: https://allevents.in/highwood/kick-off-to-summer-carnival/200029870338531 - **Venue**: 406 Sheridan Rd, Highwood, IL 60040-1309, United States - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9jYzIwOWViOTViN2MxOTUyMWU0NDExYzM5NjliYzhiYzdlMzU5YTE3ZDg2NTYwNTZlZjdjNDY0ZDhiYzFmZTRiLXJpbWctdzEyMDAtaDY3NS1kYzFhMzI0Ni1nbWlyP3Y9MTc3ODcyMzUyMA.avif - **Categories**: carnivals - **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 - **Interested Audience**: - Count: 489 - **Date**: Wed Jun 03 2026 at 03:30 pm (-05:00) - **Event URL**: https://allevents.in/highwood/highwood-evening-gourmet-market-with-music-by-stevie-craig-band-sponsored-by-bella-via/200029732862053 - **Venue**: 111 Highwood Ave, Highwood, IL, United States, Illinois 60040 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvNGNhODczNTM3MDIzZDI0MDEwYzZiNTgxY2NkZThkYTZhMDUyNmE2ZjRjOTUwMTI1NDJhYTQzMmM5YjY2OGQ0My1yaW1nLXcxMjAwLWg4OTktZGNhOWJmZTAtZ21pcj92PTE3NzcxODYwNDU.avif - **Categories**: music, entertainment, food-drinks, live-music, concerts, meetups - **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**: Low-reen & Harpdog and Friends host the 3rd Tuesday Blues Jam @ Wooden Nickel! - **Description**: Come join Low-reen & Harpdog and the Wooden Nickel House Band for a night of Northshore Blues! HOT Blues & COLD Brews! Players of all skill levels welcome. Bring your instruments & cables, drumsticks. Friendly neighborhood joint with big drink - **Interested Audience**: - Count: 14 - **Date**: Tue May 19 2026 at 07:00 pm – Tue May 19 2026 at 10:00 pm (-05:00) - **Event URL**: https://allevents.in/highwood/low-reen-and-harpdog-and-friends-host-the-3rd-tuesday-blues-jam-wooden-nickel/200029809047758 - **Venue**: Legendary Wooden Nickel - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy85NDc2YzU5YWRkMjQwYjkwODdjMjExZmQ5NDE0ZTRiMjBlN2YxMzY3NWI3MjA2ZTljMGUwNTY3ZTQyN2QwYjRkLXJpbWctdzEwNTYtaDgxNi1kYzE1MTYxNy1nbWlyP3Y9MTc3ODgyMDE5NA.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 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy84ZWU4Y2I3NjlhNjM0ZjlkOWE1NTUxMDQ0NDFmNWM5ZGMzNTIxZTA1ZjllNDU3MTI3MWVlYjFkNjE5NDFmZDNhLXJpbWctdzEyMDAtaDUwMy1kY2ZlZmZmZi1nbWlyP3Y9MTc3ODQzNzY3MQ.avif - **Categories**: entertainment, music, parties, live-music - **Event Name**: Windy City Rev Ups - Live at The Toadstool Pub - **Description**: FRIDAY, MAY 29, 2026 - THE TOADSTOOL PUB - 327 Waukegan Ave, Highwood, IL 8 PM "Live Band" Featuring Windy City Rev, Mickey Gentile, Big John Abbate, and fireball guitarist "The Mitch" performing a full throttle mix of rock, blues, dance and swing music, - **Interested Audience**: - Count: 8 - **Date**: Fri May 29 2026 at 08:00 pm – Fri May 29 2026 at 11:00 pm (-05:00) - **Event URL**: https://allevents.in/highwood/windy-city-rev-ups-live-at-the-toadstool-pub/200029835819242 - **Venue**: The Toadstool Pub - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy80ODgxNTY2ZWZhNmI1NjExNjc4Mzc3NDZmMzY1ODM0YjM1MzRkZTI0OThkMzY5M2MzN2ZlYmEzMTI4NjY5ZGQ1LXJpbWctdzEyMDAtaDEwNjktZGNmZmZmZmYtZ21pcj92PTE3NzY3MDgzMzg.avif - **Categories**: entertainment, music, performances, live-music - **Event Name**: Deadfest Band at 28 Mile Distilling - **Description**: The second Wednesday of every month come join us for great music and feast on all you can eat pizza for only $10 bucks!! - **Interested Audience**: - Count: 41 - **Date**: Wed Jun 10 2026 at 07:00 pm – Wed Jun 10 2026 at 10:00 pm (-05:00) - **Event URL**: https://allevents.in/highwood/deadfest-band-at-28-mile-distilling/200029902442252 - **Venue**: 28 Mile Distilling Co. - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy8yNTBlZTQzM2YxNDk1ZjRhZTg2ZTc3NDk1OGIzNzkyMDg0ZGI1N2JkZjBkMGFhMWRjOWIwN2FmYmQxOTNmZGU2LXJpbWctdzEyMDAtaDc3Ni1kYzA1MDQ3Ni1nbWlyP3Y9MTc3Nzk3Nzg4NQ.avif - **Categories**: music, entertainment ## 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**: 🍅 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=1778186696 - **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**: 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=1777125157 - **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**: Inferno Fest with music by Los Perros Cubanos🌶️ - **Description**: Highwood, are you ready to feel the HEAT?🌶️ Celebrate Highwood is fired up to bring you summer’s hottest event, Inferno Fest, with spicy food and beverages to test the taste buds of the most fearless food enthusiasts! From fiery twists on American, Itali - **Venue**: 111 North Ave, Highwood, IL 60040-1521, United States - **Banner**: https://cdn-az.allevents.in/events1/banners/2dfd5b7da3b9b6f9d4f9f40db889935a226a64bb02a59cdb01ffc09053278f47-rimg-w1200-h756-dcffffff-gmir?v=1778221836 - **Event Name**: 🍹Highwood’s Margarita Night with music by South of Disorder, sponsored by the Budnik Family! - **Description**: 🍹 Step into summer at Highwood’s Margarita Night! Get ready to break out the Hawaiian shirts, flip‑flops, and leis as we bring full parrothead spirit to the Wednesday Evening Gourmet Market. Margarita Night is set to transform Everts Park with tropical e - **Venue**: 111 North Ave, Highwood, IL 60040-1521, United States - **Banner**: https://cdn-az.allevents.in/events2/banners/a221d08636223fc52d172f26e8ce12fe377233e2da32be5678f7323aad3faf56-rimg-w800-h533-dc1a1615-gmir?v=1778359482 - **Event Name**: Highwood Evening Gourmet Market - **Description**: There’s nothing quite like summer evenings in Highwood, and the Evening Gourmet Market is where it all begins. Every Wednesday, Everts Park comes alive with the best of our community: incredible food, local artisans, live music, and the unmistakable energ - **Venue**: 111 North Ave, Highwood, IL 60040-1521, United States - **Banner**: https://cdn-az.allevents.in/events9/banners/5837c4fda21b4951e6ec6d9913c2080697f931630fa316b7c7f3a9feaa1ed4a9-rimg-w1200-h899-dca9bfe0-gmir?v=1769892149 ## Browse Entertainment Events by Date - [Entertainment Events Today in Highwood](https://allevents.in/highwood/entertainment--today) - [Entertainment Events This Weekend in Highwood](https://allevents.in/highwood/entertainment--this-weekend) - [Entertainment Events in May in Highwood](https://allevents.in/highwood/entertainment--may) - [Entertainment Events in June in Highwood](https://allevents.in/highwood/entertainment--june) ## FAQs - **Q**: What are the top Entertainment events in Highwood? - **A:** 🧄 Garlic Fest 2026 with music by A Tribute to Old Blue Eyes, sponsored by Scotty's on Sheridan (Wed Aug 12 2026 at 04:30 pm at 111 North Ave, Highwood, IL 60040-1521, United States), Highwood Days Carnival & Taste of Highwood🎡 (Fri Jul 17 2026 at 05:00 pm at 111 North Ave, Highwood, IL 60040-1521, United States), Kick-Off to Summer Carnival 🎪 (Fri Jun 05 2026 at 05:00 pm at 406 Sheridan Rd, Highwood, IL 60040-1309, United States), Highwood Evening Gourmet Market with music by Stevie Craig Band, sponsored by Bella Via (Wed Jun 03 2026 at 03:30 pm at 111 Highwood Ave, Highwood, IL, United States, Illinois 60040), Kevin Purcell & the Root Doctors play Toadstool Pub (Fri May 22 2026 at 08:00 pm at The Toadstool Pub). - **Q**: What Entertainment 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), Low-reen & Harpdog and Friends host the 3rd Tuesday Blues Jam @ Wooden Nickel! (Tue May 19 2026 at 07:00 pm at Legendary Wooden Nickel), Victor Brown Band at Toadstool Pub in Highwood (Sun May 24 2026 at 03:00 pm at The Toadstool Pub), Windy City Rev Ups - Live at The Toadstool Pub (Fri May 29 2026 at 08:00 pm at The Toadstool Pub). - **Q**: How can I find Entertainment events in Highwood? - **A:** You can discover upcoming Entertainment 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 Entertainment 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 Entertainment events in Highwood? - **A:** Some popular venues hosting Entertainment events in Highwood include 111 North Ave, Highwood, IL 60040-1521, United States, 406 Sheridan Rd, Highwood, IL 60040-1309, United States, 111 Highwood Ave, Highwood, IL, United States, Illinois 60040. - **Q**: What is the price range for Entertainment events in Highwood? - **A:** Prices for Entertainment events in Highwood range from USD 25 to USD 80. Many events also offer free entry. - **Q**: Who are the top organizers for Entertainment events in Highwood? - **A:** Popular organizers hosting Entertainment events in Highwood include Celebrate Highwood, Kevin Purcell & the Root Doctors, Low-reen's Live Blues. - **Q**: Are there any online Entertainment events available? - **A:** Yes, many Entertainment 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 Entertainment events in Highwood? - **A:** Follow the Entertainment category on AllEvents.in to get notified when new Entertainment events are listed in Highwood. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/58/5efbefdb8e438db5c829e697673309/Maskgroup-3-.webp ## Entertainment events from nearby cities - [Entertainment events in Deerfield](https://allevents.in/deerfield-il/entertainment) - [Entertainment events in Lake Forest](https://allevents.in/lake-forest-il/entertainment) - [Entertainment events in Northbrook](https://allevents.in/northbrook/entertainment) - [Entertainment events in Lincolnshire](https://allevents.in/lincolnshire/entertainment) - [Entertainment events in Glencoe](https://allevents.in/glencoe-il/entertainment) - [Entertainment events in Lake Bluff](https://allevents.in/lake-bluff/entertainment) - [Entertainment events in Northfield](https://allevents.in/northfield-il/entertainment) - [Entertainment events in Winnetka](https://allevents.in/winnetka-il/entertainment)