All Upcoming events

• Sat, 17 Jan, 2026 - 08:00 PM

  Big O's Sports Bar Comedy Show

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

  18+ Interested
• Sat, 17 Jan, 2026 - 07:00 PM

  Sheriff Jeff Connor's 5th Annual Trivia Night

  KC Hall Highland Il

  107+ Interested
• Sat, 28 Feb, 2026 - 07:00 PM

  2nd Annual 90's Country Night

  2005 PARK HILL DRIVE, HIGHLAND IL

  54+ Interested
• Sat, 24 Jan, 2026 - 06:00 PM

  Borderline & Line Dancing at The Olde Wicks Factory

  The Olde Wicks Factory

  USD 5
• Fri, 13 Feb, 2026 - 06:00 PM

  Dueling Pianos by the Twilight Tunes on Feb 13th, 2026!

  The Olde Wicks Factory

  USD 50
• Fri, 13 Feb, 2026 - 07:00 PM

  Pre-Valentine’s Day Dueling Pianos at Olde Wicks Factory!

  The Olde Wicks Factory

  21+ Interested
• Sat, 21 Feb, 2026 - 12:00 PM

  Mardi Gras Party @ Old Time Pub with Cajun Buffet & Live Music: Zydeco Crawdaddy's

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

  15+ Interested
• Sat, 25 Apr, 2026 - 10:00 AM

  Spring Artisan Market

  12760 Troxler Ave, Highland, IL

  129+ Interested
• Sun, 25 Jan, 2026 - 11:30 AM

  Annual Congregational Meeting

  2307 Broadway, Highland, IL, United States, Illinois 62249

  11+ Interested
• Wed, 04 Feb, 2026 - 06:00 PM

  Ladies Bible Study - Jonah

  Family Bible Church

  6+ Interested
• Fri, 16 Jan, 2026 - 07:00 PM

  2026 Trivia Night

  12454 State Route 143, Highland, IL 62249-1072, United States

  37+ Interested
• Sat, 14 Feb, 2026 - 07:00 PM

  Highland Dance Party Night - Sat. Feb 14th - Theme: Love In Paris

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

  17+ Interested
• Sat, 07 Feb, 2026 - 06:30 PM

  Madison County Fair Chicken Fundraiser Dance

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

  92+ Interested
• Sun, 22 Feb, 2026 - 09:00 AM

  Sunday AM Christian History Study 9:00 & 10:30 AM

  2307 Broadway, Highland, IL, United States, Illinois 62249

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

  Holthaus Classic 2026

  212 Walnut street HiTop Bowl, Highland, IL

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

  Dairy Day at the Madison County Fairgrounds!

  Madison County Fairgrounds

  116+ Interested
• Sun, 18 Jan, 2026 - 05:30 PM

  Winter Party

  Korte Rec Center

  39+ Interested
• Sat, 17 Jan, 2026 - 10:00 AM

  Winter Crafty Saturday

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

  22+ Interested
• Fri, 24 Apr, 2026 - 07:00 PM

  Frozen the Musical presented by Highland High School

  Highland Elementary Auditorium

  56+ Interested
• Sat, 31 Jan, 2026 - 09:00 AM

  Crafting with Heart

  Knights Of Columbus

  106+ Interested
• Fri, 27 Feb, 2026 - 06:30 PM

  Daddy Daughter Date Night '26

  Mosaic Church - Highland

  Free
• Thu, 22 Jan, 2026 - 06:00 PM

  Story Time and Craft with Mrs. Pence

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

  12+ Interested
• Sun, 15 Feb, 2026 - 10:30 AM

  72nd Annual Sausage Supper

  721 9th St, Highland, IL, United States, Illinois 62249

  123+ Interested
• Thu, 05 Feb, 2026 - 09:00 AM

  Spring Women's Thursday AM Bible Study

  2307 Broadway, Highland, IL, United States, Illinois 62249
• Wed, 14 Jan, 2026 - 07:00 PM

  Highland Line Dance Lessons 7-9PM

  1900 VFW Rd, Highland, IL 62249-2343, United States
• Sat, 07 Mar, 2026 - 08:30 AM

  3rd Annual Clays for Childhood Cancer

  Highland Pistol & Rifle Club Inc

  48+ Interested
• Fri, 23 Jan, 2026 - 05:00 PM

  The Mom Life Summit — Overwhelmed To Winning

  Towne Square Terrace

  55+ Interested
• Sat, 31 Jan, 2026 - 01:00 PM

  Crafted with Heart Valentines Market

  KC Hall Highland Il

  6+ Interested
• Sat, 17 Jan, 2026 - 08:00 PM

  Next Stop Comedy at Big O's Sports Bar

  Big O's Sports Bar Highland Square IL

  8+ Interested
• Sat, 24 Jan, 2026 - 06:00 PM

  Highland High School NYC Trivia Night Fundraiser

  2005 Lindenthal Ave. Highland IL 62249

  36+ Interested
• Thu, 05 Mar, 2026 - 06:45 PM

  HCWC Monthly Meeting - March

  Hope Lutheran Church Highland

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

  MTG: Lorwyn Eclipsed Prerelease

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

  5+ Interested
• Sat, 28 Mar, 2026 - 11:00 AM

  2026 Clinton County Classic

  Madison County Fairgrounds, Highland, IL, United States, Illinois 62249

  23+ Interested
• Sat, 19 Sep, 2026 - 08:30 PM

  Classic Crush @ The Corner Keg

  The Corner Keg Pub

  6+ Interested
• Fri, 06 Feb, 2026 - 05:00 AM

  KRC Member Appreciation Day

  Korte Rec Center

  28+ Interested
• Sat, 07 Feb, 2026 - 06:00 PM

  Music Trivia Night

  Lindendale Park

  26+ Interested
• Fri, 08 May, 2026 - 06:00 PM

  Glow Golf Fundraiser

  Country Club Rd, Highland, IL 62249, United States

  13+ Interested
• Sat, 07 Feb, 2026 - 08:00 PM

  BnB @ Madison County Chicken n Beer Dance

  Madison County Fairgrounds

  60+ Interested
• Fri, 31 Jul, 2026 - 05:00 PM

  THE GREENHOUSE FLORIST & GIFT SHOP with TGNY ACOUSTIC

  The Greenhouse Florist & Gift Shop

  5+ Interested
• Sun, 03 May, 2026 - 10:00 AM

  100 Mile Club Celebration

  2520 Poplar St, Highland, IL, United States, Illinois 62249

  14+ Interested
• Sun, 18 Oct, 2026 - 11:00 AM

  Jethro Makes 3 + Paul @ 2026 Moose Chili Cook-off

  Highland Square

  6+ Interested
• Sat, 17 Jan, 2026 - 01:00 PM

  Clean Out for Change: Item Collection benefiting Eden's Glory

  620 13th St, Highland, IL 62249-1836, United States

  10+ Interested
• Sat, 21 Feb, 2026 - 06:00 PM

  2026 Mouse Races - Supporting HHS baseball, 11U Illinois Tiger baseball, and So IL 60's Softball

  Highland Knights of Columbus Hall

  36+ Interested
• Fri, 20 Feb, 2026 - 06:00 PM

  3rd Annual Trivia Night

  12846 Daiber Rd, Highland, IL

  8+ Interested
• Sat, 31 Jan, 2026 - 07:30 AM

  Galentine’s Day Second Annual Shopping Bash! 💕🛍️

  Michael's Coffee Shop

  84+ Interested