Baraboo often gets lumped in with the neighboring Wisconsin Dells. But that doesn’t give it its due: Long before the waterslides next door, there were elephants and railcars here, part of one of the most ambitious entertainment empires in America. From 1884 to 1918, Baraboo served as the winter headquarters of the Ringling Bros. circus, and that big-top bravado still lingers.
On the town’s western outskirts, check into Fireside Cabins, which lives up to its name with stone fire pits for many of the 12 units and a large communal one for the rest. (Not to mention a bar on the premises.) When you are ready to leave the wooded seclusion, make the two-mile trip to the town square, anchored by the county courthouse, to start your shopping adventures. Check out Bekah Kate’s, a kitchenware and home store that pairs over-the-top tablescapes with a massive olive oil tasting bar. A block over, Johnny’s Girl Boutique is a cute-outfit repository of denim, soft knits, and easy dresses.
Between them is Powerline Coffee Co., which is serious about beans — and its pastry case. Powerline has become the morning stop for hikers fueling up before tackling Devil’s Lake State Park, a 10-minute drive away. The 500-foot quartzite bluffs there rise over the eponymous expanse of clear water. For the payoff view, hike up the East Bluff or Balanced Rock Trails; the lake-and-valley panorama will inevitably wind up on your camera roll.
Want more nature? Head across town to the Crane Discovery Center, a conservation park at the International Crane Foundation headquarters. It’s the only place in the world to see all 15 species of these long-legged wading birds. Trails, some paved, wind through restored prairie and wetland habitats, where you’ll spot endangered whooping cranes and others you’d never encounter otherwise.

Late afternoons are all about Balanced Rock Winery, where cold-hardy varietals grow on former farm fields and the light turns golden fast. Evenings can be split two ways: Wiscocktail Lounge reframes the classic Wisconsin tavern (think Black Squirrels and brandy old-fashioneds) in a room lined with archival tavern photography; Driftless Glen Distillery goes niche, transforming locally grown grain and aquifer-fed water into rye and bourbon in a 44-foot column still.
Don’t leave town without doing the obvious. At Circus World, a museum full of Ringling Bros. lore, you can ogle impossibly ornate restored circus wagons and watch live performers under a big top. Less than a mile away, step into the Al. Ringling Theatre, a 1915 Beaux-Arts movie theater that was built with circus money and has been handsomely restored for live performances.

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