Entertainment & Events in Woodstock, Illinois

Night Life

DC Cobbs Bar & Restaurant 815-206-5580
226 Main Street
Woodstock, IL 60098
Located on the historic Woodstock Square
The nightly hot spot for Woodstock is DC Cobbs. It features live music, DJs, pool tables, darts and more. A menu is offered seven days a week from 11am untill after midnight. more

Concerts & Performances

Woodstock Mozart Festival 815-338-5300
121 Van Buren Street
Woodstock, IL 60098
Three weekends of orchestral and chamber music performances are held annually in July and August in the historic 1880's Woodstock Opera House. Recognized conductors and guest artists perform at this rare European-like venue, allowing patrons to enjoy the music of Mozart in different performance styles. more
City Band Concerts in the Square 815-338-5300
Located at the Historic Woodstock Square
During the summer you can enjoy City Band Concerts and Ice Cream Socials on the Square, one of Woodstock’s longest traditions. Bring a blanket or lawn chair and be entertained.
Off Square Music 815-338-5164
221 Dean Street
Woodstock, IL 60098
Located at the Unitarian Church
Monthly folk concerts, hosted by a not-for-profit organization, are held every third Saturday of the month, beginning at 8PM. An intimate setting, a state-of-the-art sound system, and good viewing from every seat in the house contribute to an enjoyable evening. more

Plays & Productions

TownSquare Players, Inc 815-338-1937
Located at the Woodstock Opera House
Established in 1968, this is the oldest active community theatre group in McHenry County. Presently the company produces two shows per year, one musical and one drama. more

Antique Shows & Auctions

YSB Car Show/Fundraiser 815-338-7360
Located in the Historic Woodstock Square
More than 100 vintage hot rods and automobiles come to Woodstock each August for this car show and fundraiser. This family friendly event features games, and a DJ.

Arts & Crafts Shows

Fair in the Square Crafters Show 815-338-2436
Located on the Historic Woodstock Square
Discover an array of handcrafted wares, as crafters from all over the Midwest come to the Historic Woodstock Square, each September for this fine craft show.

Festivals & Fairs

Woodstock Folk Festival 815-338-4245
3314 Elaine Drive
Woodstock, IL 60098
Located on the Historic Woodstock Square.
This annual outdoor musical festival takes place on the third Saturday in July. It features folk, blues, Latin and Celtic music, as well as storytelling. A Children's Area, Open Mike Stage, and Story Stage are all part of the fun. The festival runs from 12:30 pm to 6:30 pm, rain or shine, so bring your lawn chairs and enjoy a great afternoon of entertainment. Spring and Fall concert series are also offered at Congregational Unitarian Church. more
Groundhog Days 815-338-2436
Every year townspeople have celebrated the filming of the movie "Groundhog Day" in Woodstock, in 1992. Food, shopping, entertainment and special events including a real, live, weather-predicting groundhog on February 2nd, a walking tour of filming sites used in the movie, a dinner/dance and auction, and much more are all part of the mid-winter fun.
McHenry County Fair 815-338-5315
The McHenry County Fair is held each August, featuring carnival rides, food booths, entertainment, animal and antique competitions, talent and queen contests, demolition derby, livestock judging, exhibits, and more.
Old Fashioned Harvest Fest & Fiddlers' Contest 815-338-2436
Located on the Historic Woodstock Square
This day long celebration held each September features a farmer's market; old-time craftspeople including weavers, spinners and quilters; vintage farm equipment; blacksmithing; woodworking; wagon rides; children's activities; and a fiddlers contest for youth and adults.

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