Dubuque, IA Outdoor Activities

Since the 1950s, Wingra Boats has outfitted groups and individuals for treks along the serene, wake-free Lake Wingra with their fleet of water vessels. Starting out with a small squad of canoes, the company has grown to include more than 100 canoes, kayaks, rowboats, and sailboats across two locations. In addition to supplying rentals, the staff keep limbs limber with yoga—performed on dry land or atop paddleboards—and strengthens cores with standup paddleboard lessons. Youngsters get in on the action during camp sessions, where they learn to cast, reel, and ask fishes for any seven cards, or paddle aboard kayaks and canoes. The staff also lead guided tours and birding expeditions, and tuck boats away for the off-season with docking and storage services.

On the waters of Lake Wingra, Madison Log Rolling's seasoned lumberjacks and jills channel the pastimes of 19th-century loggers, who would spend downtime competing to see who could balance the longest atop logs that were ferrying downriver. In 2010, Olivia Judd and Shana Martin started their log-rolling requiem to preserve and share this regional sport with newcomers. Instructors demonstrate the art of softly skimming the feet across the surface of the log to stay balanced. Beginner classes allow students to practice log rolling while showing how the sport can improve one's balance, agility, mental fortitude, and ability to pull off a plaid flannel tuxedo. Madison Log Rolling offers log-rolling classes, boom-rolling classes, and events for team building and birthdays.

Aside from hosting the Oregon youth hockey program, the nonprofit Oregon Community Sports Arena welcomes ice dancers to its multifunctional indoor rink for open skate, family skate, open hockey, and speed skating. Hockey and broomball teams occupy the icy terrain throughout the week, and expert instructors oversee regular skating schools and athletic camps on the frosty floors. An onsite shop supplies skaters with apparel and used sporting goods, and a large community room hosts regular open martial-arts classes and can accommodate birthday parties of up to 150 guests or 500 Lilliputians.

Though Ted Davis sits in the back of a green New Standard Model D-25 biplane, he won't be taking a nap. Originally built in 1929 to perform stunts and give rides—or barnstorming, as it was known—the D-25 can host up to five people on every flight—four passengers in the front and Davis, a certified commercial pilot, at the rear controls. Today, its hunter-green fuselage has been fully restored and carefully maintained to comply with modern FAA standards. In this steed, Davis, who has logged more than 5,500 flying hours since his first ascent at age 16, continues the barnstorming tradition, escorting passengers on bird's-eye views of the Wisconsin landscape as Icarus struggles to keep pace with his homemade penguin wings.

Along with his dogs Hazel and Gus, Wisconsin Adventures LLC's owner Rodrigo Camacho leads hunting groups in search of quail, pheasants, grouse, and other upland birds. Their quests take them across south-central Wisconsin's scenic countryside, which is a mixture of sprawling cropland, open fields, and densely wooded terrain. Because most hunts take place on privately owned farms, they don't require licenses or permits, which allows Mr. Camacho to accommodate everyone from first-timers to reincarnations of Davy Crockett. Mr. Camacho can also set up clay-shooting targets and train dogs in the arts of pointing and flushing.