All Upcoming events

• Sat, 22 Nov, 2025 - 10:00 AM

  2025 Fall Artisan Market

  Highland High School

  818+ Interested
• Fri, 28 Nov, 2025 - 06:30 PM

  Highland Chamber of Commerce Lighted Christmas Parade

  Highland Square

  3024+ Interested
• Sat, 06 Dec, 2025 - 10:00 AM

  Cookie Crumb Trail

  Highland Square

  1493+ Interested
• Sat, 06 Dec, 2025 - 09:00 PM

  Every Little Thing Band Performing at Corner Keg!!

  The Corner Keg Pub

  8+ Interested
• Fri, 28 Nov, 2025 - 09:00 PM

  Hunter Sharp Live - Christmas Parade After Party at Old Time Pub

  12258 Highland Road, Highland, IL, United States, Illinois 62249

  18+ Interested
• Thu, 13 Nov, 2025 - 06:00 PM

  Dementia Support Group- San Gabriel Highland

  2509 Frank Watson Pkwy, Highland, IL, United States, Illinois 62249
• Fri, 14 Nov, 2025 - 08:00 PM

  Tom O DJ at Old Time Pub

  Old Time Pub
• Thu, 13 Nov, 2025 - 07:00 PM

  Bingo Night

  1900 VFW Rd, Highland, IL, United States, Illinois 62249

  4+ Interested
• Thu, 13 Nov, 2025 - 06:00 PM

  Veterans Day Presentation

  1001 9th St, Highland, IL, United States, Illinois 62249

  5+ Interested
• Sat, 22 Nov, 2025 - 10:00 AM

  Pop-Up Cookie Stand

  Twice the Ice Highland, IL (Highland, IL)

  4+ Interested
• Fri, 14 Nov, 2025 - 04:00 PM

  Fish Fry Friday

  1900 VFW Rd, Highland, IL, United States, Illinois 62249
• Wed, 12 Nov, 2025 - 07:00 PM

  Line Dancing Lessons

  1900 VFW Rd, Highland, IL, United States, Illinois 62249
• Sat, 15 Nov, 2025 - 08:30 AM

  Boot Camp Pop Up

  Korte Rec Center

  8+ Interested
• Sun, 16 Nov, 2025 - 10:00 AM

  New sermon series! Of God and Money

  820 Mulberry, Highland, IL
• Wed, 19 Nov, 2025 - 06:00 PM

  Night of Thx!

  1317 Pestalozzi St, Highland, IL, United States, Illinois 62249

  36+ Interested
• Fri, 28 Nov, 2025 - 04:00 PM

  Black Friday Popup Sale

  1007 Washington Street OPEN Wednesday through Friday 11-5 Saturdays 10-2, Highland, IL
• Sat, 15 Nov, 2025 - 10:00 AM

  Pop-Up Cookie Stand!

  Twice the Ice Highland, IL (Highland, IL)

  4+ Interested
• Sat, 06 Dec, 2025 - 09:00 AM

  Santa's Workshop - A FREE Christmas Experience For Kids

  Highland Illinois Masonic Lodge 583

  21+ Interested
• Sat, 13 Dec, 2025 - 10:00 AM

  Free Photo with Santa

  1007 Washington Street OPEN Wednesday through Friday 11-5 Saturdays 10-2, Highland, IL
• Sun, 23 Nov, 2025 - 11:00 AM

  Holiday Sip & Shop 2025🎄🎁

  The Olde Wicks Factory

  4349+ Interested
• Sun, 23 Nov, 2025 - 10:30 AM

  Sunday 10:30 Study "All Things New"

  2307 Broadway, Highland, IL, United States, Illinois 62249
• Sat, 29 Nov, 2025 - 10:00 AM

  Small Business Saturday 15% off Storewide Sale

  1007 Washington Street OPEN Wednesday through Friday 11-5 Saturdays 10-2, Highland, IL
• Sat, 13 Dec, 2025 - 07:00 PM

  Christmas Concert: Sing out! Ring out!

  St. Paul Catholic Church Highland

  57+ Interested
• Sat, 22 Nov, 2025 - 05:00 PM

  Thanksgiving for the Community

  Highland Illinois Masonic Lodge 583

  21+ Interested
• Sat, 29 Nov, 2025 - 09:00 AM

  Small Business Saturday - Caught in the Act

  1216 Main St, Highland, IL, United States, Illinois 62249

  307+ Interested
• Fri, 12 Dec, 2025 - 05:00 PM

  Chamber Holiday Happy Hour

  Lindendale Park Ballroom

  106+ Interested
• Sun, 11 Jan, 2026 - 11:00 AM

  Olde Wicks Factory Wedding Show | Bride Registration (1/11/26)

  The Olde Wicks Factory

  Free
• Wed, 19 Nov, 2025 - 07:00 PM

  Highland - Line Dance Lessons 7-9PM

  1900 VFW Rd, Highland, IL 62249-2343, United States

  4+ Interested
• Thu, 20 Nov, 2025 - 12:00 PM

  Resident & Family Thanksgiving Meal! 🦃

  1450 26th St. , Highland, IL, United States, Illinois 62249
• Sat, 15 Nov, 2025 - 05:00 PM

  Pokemon Trade Night!

  820 Main Street, Highland, IL, United States, Illinois 62249

  13+ Interested
• Sat, 06 Dec, 2025 - 04:00 PM

  Highland Holiday Home Tour

  Cedarhurst Senior Living of Highland

  USD 29
• Sat, 06 Dec, 2025 - 09:30 AM

  Gingerbread House Decorating

  801 Washington St, Highland, IL

  11+ Interested
• Sun, 07 Dec, 2025 - 10:00 AM

  Santa Paws

  803 3rd St, Highland, IL, United States, Illinois 62249

  50+ Interested
• Sat, 03 Jan, 2026 - 07:00 PM

  Mouse Races - Roughnecks and Lady Roughnecks

  KC Hall Highland Il

  53+ Interested
• Fri, 05 Dec, 2025 - 06:30 PM

  AlphAs Christmas Party - For the Ladies!

  Highland Knights of Columbus Council 1580

  54+ Interested
• Sat, 18 Apr, 2026 - 05:00 PM

  Raise the Roost: EvUCC Dinner Auction 2026

  Knights of Columbus

  27+ Interested
• Sat, 15 Nov, 2025 - 12:00 PM

  MTG: Avatar the Last Airbender Prerelease

  820 Main Street, Highland, IL, United States, Illinois 62249

  5+ Interested
• Sat, 13 Dec, 2025 - 08:30 PM

  ShortMist @ The Corner Keg

  The Corner Keg Pub

  15+ Interested
• Sat, 17 Jan, 2026 - 12:00 PM

  MTG: Lorwyn Eclipsed Prerelease

  820 Main Street, Highland, IL, United States, Illinois 62249
• Sat, 22 Nov, 2025 - 10:00 AM

  Raising Kids in a Digital World

  1001 9th St, Highland, IL, United States, Illinois 62249

  16+ Interested
• Thu, 20 Nov, 2025 - 04:00 PM

  A Wicked Weekend on the Highland Square

  914 Main Street, Highland, IL, United States, Illinois 62249

  311+ Interested
• Thu, 20 Nov, 2025 - 06:00 PM

  Illinois Family Reading Night

  1001 9th St, Highland, IL, United States, Illinois 62249

  15+ Interested
• Sat, 17 Jan, 2026 - 12:00 PM

  MTG: Lorwyn Eclipsed Store Champ

  820 Main Street, Highland, IL, United States, Illinois 62249
• Fri, 12 Dec, 2025 - 06:30 PM

  Digimon: Evolution Cup

  820 Main Street, Highland, IL, United States, Illinois 62249
• Fri, 21 Nov, 2025 - 10:00 AM

  Last Pop Up Party of 2025!

  810 and 808 Broadway, Highland, IL

  54+ Interested
• Sat, 31 Jan, 2026 - 02:00 PM

  Holthaus Classic 2026

  212 Walnut street HiTop Bowl, Highland, IL

  30+ Interested
• Mon, 17 Nov, 2025 - 10:00 AM

  Preschool Story Time

  1001 9th St, Highland, IL, United States, Illinois 62249
• Wed, 26 Nov, 2025 - 06:00 PM

  Wild Ride Wednesday @ Old Time Pub

  12258 Highland Road, Highland, IL, United States, Illinois 62249

  23+ Interested
• Wed, 17 Dec, 2025 - 11:00 AM

  🎅✨ Santa’s Senior Social!

  1450 26th St. , Highland, IL, United States, Illinois 62249

  4+ Interested
• Sun, 23 Nov, 2025 - 04:00 PM

  UVS: Guilty Gear Strive Prerelease

  820 Main Street, Highland, IL, United States, Illinois 62249
• Sat, 07 Feb, 2026 - 06:30 PM

  Madison County Fair Chicken Fundraiser Dance

  2025 Park Hill Dr, Highland, IL, United States, Illinois 62249

  52+ Interested
• Sat, 22 Nov, 2025 - 07:00 PM

  HIGHLAND DANCE Night - Sat, Nov 22nd - THEME: Goin' Country

  1900 VFW Rd, Highland, IL 62249-2343, United States

  33+ Interested
• Thu, 22 Jan, 2026 - 06:30 PM

  Book Club

  1001 9th St, Highland, IL, United States, Illinois 62249

  18+ Interested
• Sat, 16 May, 2026 - 10:00 AM

  Dairy Day at the Madison County Fairgrounds!

  Madison County Fairgrounds

  89+ Interested
• Sun, 23 Nov, 2025 - 12:00 PM

  Me N D at Holiday Sip n Shop

  The Olde Wicks Factory

  20+ Interested
• Thu, 15 Jan, 2026 - 05:00 PM

  Business After Hours

  Knights of Columbus

  41+ Interested
• Sun, 21 Dec, 2025 - 03:00 PM

  2025 Highland Muny Band Christmas Concert

  Weinheimer Center

  120+ Interested
• Mon, 01 Jun, 2026 - 08:00 AM

  Kids Cooking Camp 2026

  Highland Ill

  7+ Interested
• Sun, 14 Dec, 2025 - 03:00 PM

  ShortMist @ Old Time Pub

  Old Time Pub

  16+ Interested
• Thu, 27 Nov, 2025 - 07:00 AM

  2025 Gobble Hobble

  Korte Rec Center

  184+ Interested
• Sat, 15 Nov, 2025 - 08:30 PM

  Fry Project returns to Corner Keg in Highland IL! 🎶🍻🎶

  The Corner Keg Pub

  8+ Interested
• Sat, 06 Dec, 2025 - 09:00 AM

  Day Retreat: Thriving (Not Just Surviving) Through the Holidays

  Mosaic Church - Highland