The popular Bill Murray film, “Groundhog Day,” certainly put Woodstock on the map. But this community was chosen as the set for a reason: It has a classic American atmosphere enhanced by historic architecture and age-old traditions. “Woodstock offers that quaint, small-town feeling,” says Meagan Begley, a Realtor with Dream Real Estate, Inc., who has lived in the area for nearly 27 years. “Small businesses, restaurants, events, a farmer’s market twice a week. It’s an active community that people are just drawn to.” Large enough to be considered a small city, residents of Woodstock learn to appreciate that it doesn’t always feel like one.
Woodstock is a famous location for filming the popular Bill Murray “Groundhog Day,”
The Woodstock Opera House has served the community since 1889.
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The Woodstock Square Historic District
The Woodstock Square Historic District is home to a variety of unique haunts. “There are so many businesses, like little boutiques and ice cream shops,” Begley says. “There is a lot to offer someone just wanting to walk around. D.C. Cobbs, in particular, is a really popular restaurant.” From gourmet burgers and hand-crafted cocktails to story time at Read Between the Lynes bookstore, Woodstock Square lives up to Begley’s description. Visitors can peruse rows of vinyl at The Records Department or shelves of soda pop at Rocket Fizz. Located a block north on Main Street, Cesaroni’s Café and Deli partners with Illinois vendors, like Two Brothers Coffee Roasters and Klein’s Farm and Garden Market, for weekly specials. Outside the Square, however, residents can shop the essentials at Walmart Supercenter or ALDI off Lake Avenue, or head to Jewel-Osco on Eastwood Drive.
Woodstock Square offers a Civil War Monument in the Historic District.
Cesaroni's Cafe & Deli offers seating and to go options in Woodstock.
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A farmer’s market held twice a week
Woodstock Square is lined with original 19th-century buildings, including the historic Woodstock Opera House. Open since 1889, it was once the site of renowned actor and producer Orson Welles’ first stage performance. Today, guests can attend trivia night at The Stage Left Café or catch a comedy show in the main theater. Out front, in the center of the square, locals gather for summer concerts and, of course, the farmer’s market. “The market is a pretty big draw in Woodstock; they hold it twice a week in the summertime,” Begley says. “Bars and restaurants sometimes close down streets for live music, and they even host a re-creation of Groundhog Day every year, just like the movie.” Notable, too, is the McHenry County Fair, held each August at the corner of Eastwood Drive and Country Club Road.
The Woodstock Opera House in Woodstock has served the community since 1889.
Fresh pastries tempt shoppers at the Indoor Woodstock Farmers Market in Woodstock.
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Old-growth trees and gardens in the front yard
Woodstock’s turn-of-the-century homes sometimes neighbor those from the early 2000s. “Down by the Square is definitely more historic,” Begley explains. “You’ll see a lot of Victorian-style homes around there.” These vintage properties may take the form of Cape Cods, modest bungalows or even Queen Annes, commonly priced between $150,000 and $400,000. Subdivisions vary, some providing spacious sidewalks while others feature tight lawns extending to the street. Regardless, homebuyers can expect to find old-growth trees and gardens decorating their neighbors’ front lawns. Farther from the Square, Colonial Revivals with more than 2,000 square feet are priced between $550,000 and $950,000. The occasional outlier might even reach the millions, but consistency is found in their attached garages, short driveways and ample yard space.
Rows of charming homes line the streets of Woodstock.
Just outside of downtown Woodstock, is rural property with acreage for families.
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Quality grade schools in multiple catchments
Students are zoned for the Woodstock Community Unit School District 200, divided between a handful of catchment areas across the city. Most will begin at either Westwood, Prairiewood or Dean Street Elementary Schools, earning an A, B-plus and B on Niche, respectively. All three primary schools feed into Creekside Middle, which ranks as the best public middle school in the county with an A-minus on Niche. Woodstock High School has an A, offering a wide range of Advanced Placement courses and dual enrollment opportunities at McHenry County College (MCC).
Woodstock High School provides students with the opportunity to partake in a dual degree.
Dean Street School in Woodstock is one of the main schools for this area.
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Year-round recreation at nearby parks and country clubs
Emricson Park is a year-round hub. The Woodstock Water Works aquatic center is open May through August, situated beside a 9-hole disc golf course, multi-use fields and playground equipment. But each winter, nearly 2 miles of the park’s primary path is cleared of snow for easy access to the famous sled hill. For a more immersive nature experience, residents head to the Kishwaukee Headwaters Conservation Area, where a paved recreation trail accompanies a canoe launch and plenty of opportunities for fishing. Both Bull Valley Golf Club and Woodstock Country Club offer exclusive amenities. The former provides a private 18-hole course, while the latter is the oldest country club in the county, with one of the top 25 best 9-hole golf courses in the U.S.
Emericson Park is a hot spot for morning walks with friends in Woodstock.
Woodstock Recreation offers pickleball courts indoors for a daily entrance fee.
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From Woodstock Station to Madison Street
Located 51 miles from Chicago’s iconic Loop, Woodstock certainly has more small-town appeal than its neighboring suburbs. But that doesn’t mean the Windy City is hard to reach. “The nice thing about Woodstock Square is that the train station is right there,” Begley points out. “You have easy access to the Metra even though you’re farther out from the city. A lot of people commute out of that station.” Paired with the Metra are a variety of bus stops both surrounding the square and lining US Highway 14, where Northwestern Medicine Woodstock Hospital sits about 4 miles south. Commuters may instead opt to take Route 47, Eastwood Drive, into the city or to reach Chicago O’Hare International Airport, a 48-mile trip southeast.
Woodstock is a cozy town with many amenities and things to do all year round.
Woodstock train station is a great place to hop on a quick train to Chicago.
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