Four Road Trips That Will Make You Glad It’s Winter

Check out these four fun (and accessible) destinations.

The lights festival in Galena, Illinois   Photo: Courtesy of Galena/Jo Daviess County Convention & Visitors Bureau

The December issue of Chicago magazine explores the many greats things to do in winter—101 of them. Here are four more: Fun and accessible road trips that will change your view on the cold season in just a matter of hours.

1. Charming Throwback

Destination: Galena, Illinois
Drive time from Chicago: 3 hours
Hop from one historic bed and breakfast to another at the Taste of Christmas Progressive Dinner on December 7, rubbing shoulders with innkeepers who dish on the history of their inn and town. Or, travel to Galena on December 14 and hope for snow during Night of the Luminaria, when 5,000 candle-lit luminaries set the streets, steps, and sidewalks aglow, all the way from Main Street to the glistening hills overlooking the town park. Plan at least an extra day to hit the slopes or the mega terrain park at Chestnut Mountain, a quick drive from the edge of town.
Where to drink: Perk up with a tipple of locally made whiskey from a barrel at the new Blaum Bros. Distilling Co., expected open by the end of November.
Where to stay: Situated on Galena’s main drag, the 1855-built DeSoto House lives up to its historic reputation; Abraham Lincoln stayed here and Ulysses S. Grant made it his presidential campaign headquarters (from $225).

2. For the Love of Hockey

Destination: Ann Arbor and Detroit, Michigan
Drive time from Chicago: 3.5 hours
The trip to eastern Michigan is not a dis to your home team, but rather a chance to size up the competition at one of the most revered hockey events second only to the Stanley Cup finals: the NHL Winter Classic on January 1. The annual game is played outdoors, and this year, the showdown between the Toronto Maple Leafs and the Detroit Red Wings takes place in Ann Arbor, where Canadians and all matter of hockey fans will get loud at the 110,000-seat Michigan Stadium, a.k.a. “The Big House.” Come a day earlier to Detroit for the Hockeytown Winter Festival (December 31), where more outdoor games for college, junior, and alumni teams light things up at Comerica Park, home of the MLB Detroit Tigers.
Where to eat: Dig into a Dutch apple, butterscotch crème, or pumpkin crumb pie at Achatz Homemade Pie Co, run by cousins to the one and only Grant Achatz.
Where to stay: Kick back in Detroit at Honor & Folly, a two-bedroom, exposed-brick inn dressed in cheery colored-glass windows and kitsch for sale from regional artists (from $165).

3. Snowy Thrills

Destination: Wausau, Wisconsin
Drive time from Chicago: 3.5 hours
The highest vertical drop in Wisconsin is the big draw for skiers and snowboarders to Granite Peak at Rib Mountain State Park, but it should not intimidate families, who will find a lot to do in forest-embraced Wausau. Wisconsin’s longest tubing runs are here, too, at Sylvan Hill Winter Recreation Area, where you can catapult down one of six chutes and back up via two tow lines. Head indoors for a unique form of bird watching at the Leigh Yawkey Woodson Art Museum. Housed in an updated 1931 English Tudor with art focused on birds, this museum has been named one of the best places worldwide for indoor bird watching. At dusk, power through the Nine Mile Forest on lighted cross-country and snowshoe trails, perfect for adventurous night excursions until 9 p.m.
Where to eat: Slide into a snug booth at The Great Dane Pub and dive into the crust of the homemade chicken potpie.
Where to stay: Small town hospitality shines at the downtown Jefferson Street Inn (from $116), a stylish boutique with full kitchens, package deals with Granite Peak, and an ice skating rink across the street.

4. Beer, Cheer, and Pork

Destination: Madison, Wisconsin
Drive time from Chicago: 2.5 hours
Take in snow-filled views from inside a cozy tavern or aromatic brewery. Start at the German-engineered Huppmann Brewhouse for a taste of the chocolatey Brown Porter at the Wisconsin Brewery, a new beer hub opened November 1 by the owners of Capital Brewery. You’ll also want to try the creamy Nightfall Lager from Pecatonica Beer Company, another new suds maker on the scene this fall; find it on tap at the Old Fashioned, a pub on Madison’s Capital Square. Venture a few miles out of town to Middleton for cheer of another sort at Death’s Door Distillery: clear spirits. All are brewed from grains and crops sourced from nearby Washington Island, including a surprisingly delicate gin.
Where to eat: Opened in September, Heritage Tavern is the latest from chef and Dundee-native Dan Fox, who culls the menu’s pork creations from his own stock of heritage breed pigs, raised at a nearby farm.
Where to stay: The mod 48-suite Hotel Red sits right across the street from University of Wisconsin’s Camp Randall Stadium (from $161).

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