Past Events


Thank you for joining our Last Dusty Boots Tour on May 13, 2023! We safely guided 150 visitors through the Old Courthouse and Sheriff’s House and saw amazing changes. Renovations are expected to be completed this summer with a grand opening you won’t want to miss.

2nd Dusty Boots Tour

Thank you for joining our 2nd Dusty Boots Tour on 10/1/22 that saw us tour the Old Courthouse and Sheriff’s House this time. Thank you to the City of Woodstock and Bulley & Andrews for making it possible. There are a lot of great things happening in the Old Courthouse Center!

Amazing Woodstock Race

Thank you for joining the Amazing Woodstock Race on 9/10/22 and supporting Friends of the Old Courthouse and Friends of the Opera House. We had great weather and great competitions with the winners, Common Denominators, pictured below with John Puzzo, President of Friends of the Opera House.

Dusty Boots Tour April 2022

Silent Auction at the Old Courthouse March 2022

We had a great turnout for the Silent Auction of Old Courthouse and Sheriff’s House furniture, fixtures, and art! Thank you to all who attended and bid on items. While many things were saved for the new tenants, we are so happy the rest of the stuff found new homes – Enjoy!

Groundhog Day 2022

Once again, crowds descended on the Woodstock Square to celebrate Groundhog Day!

Gingerbread House Walk 2021

The 6th Annual Gingerbread House Walk was displayed at the Old Courthouse from 11/26/21-12/19/21. Our judges were Deputy Mayor Darrin Flynn, Doreen Paluch, and Senator Craig Wilcox who awarded prizes for Most Creative, Most Beautiful, Most Delicious, and Funniest. The People’s Choice Award was chosen by voting with their dollars at the Lighting of the Square and the winner was “Christmas at the Castle!”

Witches and Wizards of Woodstock 2021

Even though it was a rainy 10/24/21, we still had a great day with lots of witches and wizards visiting our “Tiny Bedroom Under the Courthouse Stairs” and taking a class with Griselda Grubb!

The Amazing Woodstock Race 2021

The Amazing Woodstock Race took place on September 18, 2021 and was a great day! Participants had so much fun and this fundraiser supported Woodstock’s three Friends groups. Like and follow us to get information on next year’s event.

Groundhog Day 2021

Groundhog Day 2021 with Woodstock Willie wearing his face shield!

2020 Winners of the Virtual Gingerbread House Walk

FOTOC Donates $10,000!

Thanks to our supporters, we were able to donate $10,000 in October 2020 to help restore the Old Courthouse and Sheriff’s House!  Pictured are FOTOC Board members, Front row: Julie Miller, Sue Stelford, and Mayor Brian Sager, second row: Terry Willcockson, Pat Kraft, Darrell Moore, and Tom Ellinghausen.


2020 Groundhog Day Tours

Our largest crowds to date – nice weather and 2/2 fell on a Sunday!  Thank you to the over 750 visitors that toured our Old Courthouse and Sheriff’s House this weekend.


2019 Lighting of the Square

We had a packed house at the Gingerbread House Walk on 11/29/19 from 4-9pm!

2019 Gingerbread House Walk

Thank you to our judges, Woodstock City Councilwoman Wendy Piersall, Woodstock Police Chief John Lieb, and McHenry County Board Member Pamela Althoff.

2019 Chamber Mixer

mixer collage

2019 Witches and Wizards of Woodstock

Thank you to our volunteer Tony Romano, for constructing our adorable “Tiny Bedroom under the Courthouse Stairs.”  We had a lot of muggles stopping by to get their picture taken.  See you next year!


2019 Dancing with the Courthouse Stars

Thank you for your support of our SOLD OUT show on 9/21/19!

Winner was Star Jodie Kurtz Osborne and Pro Mark Thomas!

Thank you to our fabulous cast!


Thank you to the fabulous Alberto Perez for his videography talents!

Thank you to Victoria McDonald for taking photographs of our event!

2019 Groundhog Day at the Old Courthouse

The Groundhog Day prognostication took place in the Woodstock Square on Saturday 2/2/2019 at 7:07am!   Afterwards, 500-600 people headed to the Old Courthouse, also on the Woodstock Square, to get warm, break a Guinness World Record, and tour the Old Courthouse!

Tours started at 7:30am and ran approximately 20-30 minutes in length. We toured areas currently closed to the general public such as the upstairs of the Old Courthouse, including the main courtroom and the recently revealed stenciled ceiling, as well as two levels of jail cells in the Sheriff’s House.

Folks also joined us in the Gould Gallery and worked on our Guinness World Record attempt at the Longest Cartoon Strip by a Team.  The record is just over a mile long and we already have over 1200 teammates and have completed about 3/4 of a mile.  No drawing talent was necessary – as we were tracing Dick Tracy comic strips.  The creator of Dick Tracy was Chester Gould, who lived in Woodstock, IL for many years.

2018 Gingerbread House Walk