47 miles from Chicago, Woodstock is on the edge of the Chicago metropolitan area. We’re close to the city with a small town, rural personality all our own.
Rich with Victorian architecture, a town square that seems frozen in time, and a world-renowned Opera House, Woodstock also has an independent streak brimming with creativity and entrepreneurship. Artists and locally-owned businesses are embraced. Our school system is a leader in dual language education. And music, whether rock, folk, jazz, country or classical, fills the air indoors and out most every night.
Real Woodstock is about spending the holiday season with family and friends in one of the prettiest Christmas-towns anywhere. From gift shopping to cutting down your family Christmas tree, there is no better place to experience the magic and charm of holidays than in Real Woodstock.
Lighting of the Square
Friday, November 23, 5-9pm
Friends and family gather on the historic Woodstock Square to kick-off the holiday season at Lighting of the Square, the day after Thanksgiving. At 7pm, a giant switch will be flipped as tens of thousands of twinkling lights illuminate the Woodstock sky. Come early and stay late for children’s activities, caroling, holiday shopping, Santa sightings, the Christmas Tree Walk at the Woodstock Opera House and Gingerbread House Walk at the Old McHenry County Courthouse.
Small Business Saturday
Saturday, November 24
Woodstock / McHenry County
If you are looking for unique artisan holiday gifts and festive treats for friends and family this season, there is no better place than Woodstock and the businesses on the charming Woodstock Square. Start
Check items off your holiday shopping list on Small Business Saturday, November 24 with local business owners in Woodstock and throughout McHenry County.
Join us in supporting local community businesses this holiday season!
Free Horse-Drawn Carriage Rides
Fridays, Saturdays & Sundays
November 24 - December 23
Go back in time and take a free ride around the Historic Woodstock Square during November and December on Fridays, Saturdays and Sundays.
Free horse-drawn carriage rides around the cobblestone-lined Woodstock Square will be offered on Small Business Saturday outside the Woodstock Opera House and will continue until December 23.
Ladies Nite Out
Thursday, November 29, 5-9pm
In Real Woodstock, holiday shopping is better with friends!
All ladies are invited to stroll, shop, eat, drink, and enjoy holiday caroling and lights with friends on the historic Woodstock Square! While Ladies Nite Out is a free event, VIP packages, which include everything from reserved parking spaces to a VIP reception, are available starting at $35.
Robin Spielberg: Spirit of the Holidays Sing-Along with Woodstock High School Madrigals (Wednesday, December 12)
One of America's most beloved pianist/composers and Steinway Artist Robin Spielberg spreads holiday cheer on the Woodstock Opera House stage at Spirit of the Holidays Sing-along on Wednesday, December 12!
The Woodstock High School Madrigal singers, directed by Brian Jozwiak, join Robin on stage as they perform Christmas carols and winter favorites. Before the concert, get a free hot chocolate at Ethereal Confections starting at 6:00 PM (first 100 cups) then join the WHS Madrigals outside the Woodstock Opera House steps at 6:50 PM for a special pre-show performance!
Woodstock High School Madrigal Singers at Ogilvie Transportation Center
Last year, Real Woodstock and the Woodstock High School Madrigal Singers teamed up in downtown Chicago during rush hour at Ogilvie Transportation Center (500 W Madison) to spread holiday cheer and promote holiday events in Woodstock! Commuters were treated to caroling and Ethereal Confections chocolate as we raffled off a free one-month Metra pass.
Explore The Woodstock Square
There is always something happening on the Woodstock Square.
Use the Real Woodstock visitor guide and map to find shopping, dining, parking and all other services on the Woodstock Square.
Woodstock Christmas Tree Farms
Planning on picking your own Christmas tree this holiday season?
Starting Friday, November 23, visit Woodstock's Oney’s Tree Farm, Moehling Christmas Tree Farm or Grandpa’s Christmas Tree Farm to get your family Christmas tree! Make a day of it in Woodstock. Visit the charming Woodstock Square before for a meal or shop for unique gifts at one of our many boutiques.
Address: 16608 Rt 14., Woodstock, IL
Open: November 23 - December 2
Hours: 9:00 am - 4:00 pm (fields close at 3:30 pm)
Other Items: Custom wreaths, centerpieces and garland, bakery treats
Other Activities: Pony rides, holiday gift shop, visit with Mrs. Claus in the North Pole House on weekends, free horse-drawn wagon rides (weekends only, 10:00 am - 3:00 pm).
Address: 10904 Bull Valley Road, Woodstock, IL
Open: November 23 and every Saturday and Sunday until December 25
Hours: 9:00 am - 4:30 pm
Other Items: Free coffee and hot chocolate, crafts and gifts, Elivan all-natural soaps and beeswax candles
Address: 13616 IL Route 176, Woodstock, IL
Open: November 23-25, December 1-2, 8-9
Hours: 9:00 am - 3:30 pm
Other Items: Free coffee and hot chocolate
Other Activities: Tractor-drawn wagon rides
Woodstock Honors its Stars of Screen and Stage with Woodstock Mural
Bringing to life a concept originating with Woodstock City Councilman RB Thompson, a wall Mural has been designed honoring four of Woodstock’s cultural legends: Chester Gould / Dick Tracy; Orson Welles; the film Groundhog Day; and “Stars of the Opera House”.
Real Woodstock is Built on a Community of Creative and Entrepreneurial Leaders
Located on the historic Woodstock Square, Silver Prairie Natural Soap Company creates home-made blends of oils and goat milk soap designed to be luxurious and promote healthy skin.
Experience a Show at the Historic Woodstock Opera House
Entertaining patrons for over 125 years, the historic Woodstock Opera House is the crown jewel of Woodstock and McHenry County. Situated on the charming Woodstock Square, this community-owned venue continues to serve its guests as a performing arts center and focal point of the community.