It’s beginning to look a lot like the holidays in Woodstock


November, 2021

Woodstock, Illinois

Real Woodstock, the Woodstock Area Chamber of Commerce and Industry and Woodstock and the City of Woodstock announces the Winter in Woodstock Holiday plans and programs for the 2021 season.


Winter in Woodstock is full of wonder.  Named the Most Festive Christmas Town in Illinois by Trips to Discover, the 2021 holiday season will live up to that distinction once again.

The unofficial kickoff to the holiday season will happen Sunday November 14th which happens to be National Pickle Day, with the launch of the Legend of the Pickle Scavenger Hunt. Members of the Kraft Heinz Claussen Pickle team will be handing out jars of cold Claussen Pickles.  Woodstock Willie and the Woodstock Pickle will both be in attendance taking pictures and sharing pickles.  Hunters have until December 12th to search out pickles hidden in Woodstock shops and restaurants.  Turn in your game card for a chance to win an IPAD and other great prizes.

The annual favorite, Lighting of the Square will once again happen in person and we couldn’t be more excited.  Friday after Thanksgiving, November 26th gather with friends and family on the Historic Woodstock Square starting at 4 pm to enjoy the new selfie spots, food trucks, carolers and Santa.  At 7 pm the ceremony will begin on the Dr. Brian Sager Bandstand followed by the famous Flip of the Switch.  Activities will go till 8 pm this year.  Lights in the Square remain lit till Groundhog Day, February 2nd, 2022.

Friday November 26th also kicks off the Woodstock Holiday Lights Contest.  Homes and Businesses entered in the official contest will begin to light the way starting the 26th and be on through December 25th.  Interested contestants must register with the Woodstock Area Chamber of Commerce and Industry prior to November 22nd.  Judging will take place between December 4th and 5th by a selected panel of Woodstock residents.  Prizes will be awarded to six category winners and a grand prize and runner up.

Small Business Saturday is more than one day in Woodstock but we pull out all the stops on November 27 the with a live broadcast with the team at McHenry’s very own Star 105.5 from 10 am to noon.  Local shops will be running great holiday specials all day too and Real Woodstock will be giving away tickets to upcoming Chicago Wolves Hockey games.

Free Carriage Rides return to Woodstock. See for yourself why Woodstock was voted the most festive Christmas town in Illinois. Enjoy the charm and enchantment of the Woodstock Square during the Holidays with a nostalgic horse drawn carriage ride around the Square. This is a first-come, first-served opportunity and a popular holiday attraction, so grab a warm beverage, dress warm, and be patiently prepared to wait in line outdoors. Due to COVID-19 precautions, blankets are not provided on the carriage any longer, so feel free to bring your own cozy blankets to keep warm. For the health and welfare of the horses, there is a 2 1/2 hour limit on their workday, so rides will end at stated time regardless of the number of patrons waiting in line at that time. Make your decision to wait accordingly, so you are not disappointed.  There are two dates for this tradition.  Saturday November 27th and Sunday December 12th.

The annual Woodstock Christmas Parade rolls through town on Sunday November 28th beginning at 2 pm with a new route and same fun. Area groups, businesses and residents are encouraged to sign up and participate.   Details and map can be found at

Cookies and Churros with Santa combines two great traditions in Woodstock on Sunday November 28th immediately following the Woodstock Christmas Parade, approximately 3 pm at Flores Banquets at 240 North Throop Street.  Sponsored by the City of Woodstock and Hispanic Connections, the public is invited to enjoy free cookies, churros and milk and visits with Santa Claus.  New this year, live reindeer sponsored by the Woodstock Area Chamber of Commerce and Industry will be set up in the parking lot for photos.

Ladies Night Out happens Thursday December 2nd with late hours and lots of fun shopping deals. Shopping specials begin at 11 am and go to 9 pm.  Sip while you shop from 5 to 9 pm with the purchase of a Ladies Nite souvenir event cup.  Free to attend with VIP passes available for purchase.  Find details at

Shop, Save & Win grows in it’s second year and adds dining.  Funded by the City of Woodstock and coordinated by the Woodstock Area Chamber of Commerce and Industry and Real Woodstock; the expanded Shop, Dine, Save & Win program is at it’s heart one that gives back to the community.  Running November 13th through December 31st the Shop, Dine, Save & Win Holiday Program is intended to stimulate retail sales in Woodstock, save you a little money on your purchases, and reward you for shopping and dining at our local small businesses with a chance to win cash prizes to share with your favorite small independent retailers and restaurants.  Please visit the WACCI website for details and list of eligible businesses.


Santa visits resume in the Hut.  The Rotary Club of Woodstock will once again host santa and his guests in the traditional Santa Hut in the Park on the square.  Reservations are required and can be made here.  Please direct questions pertaining to Santa to the Rotary Club of Wooodstock.

Contact Real Woodstock for details at 815-338-2436 or