The Great Highwood Pumpkin Festival
Click here for more info on the 5K Pumpkin Run!
Saturday, October 22nd - Full Day of Festivities


  • 9:00am - 5k Pumpkin Run & Kids Dash sponsored by Equinox, AthletiCo, Bridie McKenna's and Whole Foods Market, with The Leukemia Research Foundation as the non-profit partner. Participants can register HERE. The first 200 to sign up receive free brunch after the run at Bridie McKenna's (non-participants are also welcome), registrants 201-300 receive a free pumpkin pie from Whole Foods Market. Run starts in front of Highwood City Hall, 17 Highwood Avenue, with a warm up and after run massages by Equinox and stretching before and after by AthletiCo. Whole Foods Market will supply bananas, water, pumpkin muffins and bagels to all runners.
  • 10:00am-9:00pm - Evening Gourmet Farmers Market with 40+ vendors in front of City Hall. A day full of pumpkin carving and counting, Kids Play Area sponsored by Whole Food Market, Pony Rides and Petting Zoo sponsored by Patch 22, live music on two different stages, eating, drinking, hayrides, and more!
  • 12Noon - Giant Pumpkin Land Regatta, featuring huge pumpkins propelled by human power in a 150-yard race from the corner of Sheridan Road and Highwood Avenue, due north. Sponsored by Lake Geneva's Pearce Farms, Gordy's Lakefront Marine, Austin Pier Services, Gage Marine and Fontana Paddle Company. Participants can sign up by emailing giantpumpkinregatta.
  • 1:00pm - Military Covenant with the City of Highwood at the Main Stage
  • 12:30-9:00pm - Live Music Live on two stages:

    MAIN STAGE
    12:30-2:00pm - The Bottle Poets - Original Pop/Rock
    1:00pm - Military Covenant with the City of Highwood
    2:15-3:45pm - Jeannie Tanner - Jazz
    4:00-5:30pm - Butterfly In Traffic -Bluesy Rock n Roll
    5:45-6:30pm - Winner of the Battle Of The Bands Announced
    6:00-9:00pm - Matt Feddermann - Pop/Rock Covers

    NORTH STAGE
    1:00-2:30pm - TBA
    2:45-4:15pm - The Mooncrickets - Classic Rock Covers
    4:30-6:00pm - Narrow Winded - Rock N Roll Covers

  • 2:00pm - Pumpkin Fest Parade, starting at Sheridan Road and Bank Lane.
  • 3:00-9:00pm - Each day of the festival will include the Highwood Evening Gourmet Farmers Market at City Hall Park (17 Highwood Ave)with some 40+ vendors, live music, haunted and fantasy hay rides, pumpkin carving stations, massive pumpkin displays, ceremonial lighting of the towers each evening at 6:30, and much more!
  • 5:30pm - The festivities culminate with the lighting and grand display to break the Guinness World Records for the most jack-o-lanterns, followed by Flash Mob/Thriller Dance in front of the Main Stage.
highwood pumpkin festival sponsors
© ** The Great Highwood Pumpkin Festival Home | Event Details | Sponsors | Press | Gallery | Get Involved