October 19 @ 9:00 am - 7:00 pm Scary Halloween Miniature Golf River's Edge Mini Golf 2205 Skokie Valley Road, Highland Park, IL, United States Free
October 19 @ 11:25 am - 12:10 pm Public Skate Public Skate Centennial Ice Arena 3100 Trail Way, Highland Park, IL, United States $7 – $11
October 21 @ 11:00 am - 1:00 pm Public Skate Centennial Ice Arena 3100 Trail Way, Highland Park, IL, United States $7 – $11
October 22 @ 10:30 am - 12:30 pm Wiggle Time Wiggle Time Recreation Center of Highland Park 1207 Park Avenue West, Highland Park, IL, United States $7 – $9
October 22 @ 11:00 am - 1:00 pm Public Skate Centennial Ice Arena 3100 Trail Way, Highland Park, IL, United States $7 – $11
October 22 @ 5:00 pm - 7:00 pm Rosewood Park Playground Community Open House Rosewood Beach Interpretive Center 883 Sheridan Road, Highland Park, Illinois
October 23 @ 7:00 am - 1:00 pm Ravinia Farmers Market Ravinia Farmers Market Jens Jensen Park 486 Roger Williams Ave, Highland Park, Illinois
October 23 @ 10:00 am - 11:00 am Stories in the Sand Stories in the Sand Rosewood Beach 883 Sheridan Road, Highland Park, IL, United States $6
October 24 @ 10:30 am - 12:30 pm Wiggle Time Wiggle Time Recreation Center of Highland Park 1207 Park Avenue West, Highland Park, IL, United States $7 – $9
October 24 @ 11:00 am - 1:00 pm Public Skate Centennial Ice Arena 3100 Trail Way, Highland Park, IL, United States $7 – $11
October 25 @ 11:00 am - 1:00 pm Public Skate Centennial Ice Arena 3100 Trail Way, Highland Park, IL, United States $7 – $11
October 25 @ 5:00 pm - 6:30 pm Fall Skating Exhibition Centennial Ice Arena 3100 Trail Way, Highland Park, IL, United States
October 25 @ 5:30 pm - 7:00 pm Jack-o’-Lantern Geocache Heller Nature Center 2821 Ridge Road, Highland Park, IL, United States $13
October 25 @ 7:00 pm - 8:30 pm Scary Skate Centennial Ice Arena 3100 Trail Way, Highland Park, IL, United States Free
October 26 @ 11:25 am - 12:10 pm Public Skate Public Skate Centennial Ice Arena 3100 Trail Way, Highland Park, IL, United States $7 – $11
October 26 @ 1:00 pm - 2:30 pm Pumpkin Pool Splash Recreation Center of Highland Park 1207 Park Avenue West, Highland Park, IL, United States $14 – $17
October 27 @ 5:30 pm - 8:30 pm Sled Hockey Benefit: HP Giants Hockey vs. Hornets Sled Hockey Centennial Ice Arena 3100 Trail Way, Highland Park, IL, United States
October 28 @ 11:00 am - 1:00 pm Public Skate Centennial Ice Arena 3100 Trail Way, Highland Park, IL, United States $7 – $11
October 29 @ 10:30 am - 12:30 pm Wiggle Time Wiggle Time Recreation Center of Highland Park 1207 Park Avenue West, Highland Park, IL, United States $7 – $9
October 29 @ 11:00 am - 1:30 pm Public Skate Centennial Ice Arena 3100 Trail Way, Highland Park, IL, United States $7 – $11
October 30 @ 7:00 am - 1:00 pm Ravinia Farmers Market Ravinia Farmers Market Jens Jensen Park 486 Roger Williams Ave, Highland Park, Illinois
October 30 @ 6:00 pm - 7:00 pm Board Meeting Board Meeting West Ridge Center 636 Ridge Road, Highland Park, IL, United States
October 31 @ 11:00 am - 1:00 pm Public Skate Centennial Ice Arena 3100 Trail Way, Highland Park, IL, United States $7 – $11
November 1 @ 4:30 pm - 6:00 pm Pumpkin Smash Hidden Creek AquaPark 1220 Fredrickson Place, Highland Park, IL, United States $5