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updated: 9/24/2012 5:09 PM

Annual Great Highwood Pumpkin Fest

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City of Highwood

It's that time of year again - the City of Highwood is bringing back the Third Annual Great Highwood Pumpkin Fest! After breaking the world record in 2011 for lighting 30,919 pumpkins throughout town at once, the Great Highwood Pumpkin Fest is thrilled to host two more exciting record-breaking events in 2012, going for a Hat-Trick (or Treat!). From Thursday through Saturday, October 18th-20th, Pumpkin Fest will attract over 60,000 people from across the country to share in a wonderful community experience.

The Great Pumpkin Fest has put the City of Highwood on the map, being recognized by trip planning company, Rand McNally and USA Today as a contender in the Best Small Towns in America "Best of the Road" competition, as well as being a Double Jeopardy answer. The City is being put on the map once again, recently announcing that their biggest festival will be the subject of a new show on HGTV this Fall, entitled "Pumpkin Wars"! Debuting on October 31st at 7pm CST, Highwood will be the focus of this one-hour HGTV special. "Property Brothers" star, Jonathan Scott, will come to Highwood to film, participate and report on the great family-friendly festival, while his brother, Drew Scott will be in Keene, New Hampshire at their Pumpkin Festival. Let the battle begin!

Please make sure to join the fun and sign up for these fun events!

Thursday, Oct. 18th --
3pm - Pumpkin Totem Pole Contest. Highwood's Bocce Courts will transform into Totem Pole Park! Beginning at 3pm, the most creative carvers who think they can create the best pumpkin totem pole will compete! Judges will announce the winner at 7:45pm. To sign up, please contact or call 847-432-6000.
7pm -- Pumpkin Pie Eating Contest. Headed up by Bent Fork Bakery on Waukegan Avenue. Sign up here:

Friday, Oct. 19th -- 
6:30pm -- Guinness World Record Attempt for the Most People Carving Simultaneously. The most pumpkins carved simultaneously is 965, achieved by 965 students at the Malvern Town Centre in Scarborough, Ontario, Canada on October 31, 2005. We need at least 975 people to break this record! If you DO NOT have an all-you-can-carve wristband, it is $10 to participate. Sign up here:

Saturday, Oct. 20th -- 
9am -- 5K/10K Pumpkin Run and Kid's Dash. Races will begin at the corner of Sheridan Road and Walker Avenue. Runners will race South and loop through Fort Sheridan on a beautiful scenic route, heading back to the start line. Sign up here:

Noon -- Giant Pumpkin Land Regatta. Participants in giant pumpkins will race South down Sheridan Road, starting at the North Gate. There will be two races -- one motorized and one not motorized. There is a $25 fee to enter, which includes a dolly. Sign up here:

4pm -- Pet Costume Contest. Held at the Main Stage. Bring your pet "dressed to kill" and ready to strut their stuff! There is a $10 fee to enter. Sign up here: