The 1993 movie Groundhog Day wasn’t filmed in Punxsutawney, Pennsylvania, but right here in Woodstock, Illinois. Bill Murray’s hapless character spent an eternity reliving the little city’s attractions. That might not be so bad. Its picturesque square packs in lots of events, including Harvest Fest, Thanksgiving Lighting Fest, Folk Fest, and Jazz on the Square. The century-old Woodstock Opera House stages everything from Mozart concertos to musical theatre; D.C. Cobb’s serves up a smart selection of regional craft beers and a dumbfounding array of burgers. What’s more, “Not many suburbs can boast an eight-screen movie theatre downtown,” brags Cort Carlson, Woodstock’s community and economic development director.
As for real-estate options, you’ll find large Victorians in the blocks nearest the square. Less expensive houses, many in new subdivisions, lie just beyond. None of them will cost you a bundle, partly because Woodstock is at the outer edge of the metro area. The median house sales price for Woodstock (and for Greenwood, a tiny town that abuts it) is still down 36 percent from the 2006 peak but is starting to bounce back.