Freeport, IL Outdoor Activities

Decorative smokestacks stretch toward the sky as Victorian red and gold decor surrounds passengers nibbling brunch in a dining salon. This scene unfolds aboard the Spirit of Dubuque, an authentic-looking paddleboat that pays homage to the century-old steamboats of the Mississippi River. Dubuque River Rides' signature vessel, it has played host to thousands of cruises filled with entertainment, meals, and improvised renditions of "Old Man River" since being christened by Iowa governor Robert Ray in 1977. Elsewhere on the river, a more modern boat cuts across the water, casting a sleek outline against the sky. The 80-foot yacht, affectionately called Miss Dubuque, sets an intimate stage for events that range from weddings to Huckleberry Finn's notorious dinner parties.

Both boats call the northern expanse of the Mississippi River their home, sharing the area with wildlife such as turtles and bald eagles. The sightseeing vessels also pass by river barges and historic structures such as the Chicago Central Pacific Railroad Bridge, which was built after the president invented Lincoln Logs in 1868. After boats return to the docks, their passengers can head over to the floating barge that houses the Ice Harbor Restaurant.

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.

Fully licensed instructors, thoroughly maintained aircrafts, and a skydiving training program licensed by the US Parachute Association ensure that a jump at Chicagoland Skydiving Center is rigorously safe—but nothing can dampen the thrill of free falling from 14,000 feet. The center’s spotless student record can be attributed both to the longevity of the program, which has been around since 1968, and to the expertise of the instructors, some of whom have made more than 15,000 jumps. Their attention to safety enables visitors to focus on the fun part: a 60-second free fall followed by a leisurely float under a parachute with countless high-fives from passing birds.

Once their feet have firmly planted on the ground, skydivers can celebrate besting Sir Isaac Newton in a spacious facility with games, a lounge, and an onsite restaurant. Instant footage provides new perspectives on daring falls, and guests can purchase pictures and videos to commemorate the event.

The Stockton Park District hosts outdoor community events throughout the year, including craft fairs, basketball tournaments, and 5K and 10K run/walks. Brothers Steve, Andy, and Tom Jordan organized the first annual 5K in 2008. They used their skills from hosting a 3-on-3 basketball tournament to plan and advertise the event. The first year, they signed up 91 runners and raised money for a tennis court behind the high school and a paper-airplane factory at the middle school. Since then, the brothers have worked to improve the race and transform it into a community event with entertainment and an increasingly challenging and interesting course.

Mike Mott and Cole Chaplin share more than just alliterative names; their mutual passion for promoting Iowa's tourism industry led them to found IA Segway together, and they continue to introduce visitors to the cultural richness of the Quad Cities with informative Segway tours. Mike and Cole command a fleet of Segway i2s—the company’s most current model—and teach tour groups how to safely operate the self-balancing steeds before blazing trails to spots of local and historic significance. Tours swing around scenic destinations such as the Figge Art Museum, McClellan Heights, and Credit Island, whose battlefield is strewn with denied credit cards that date back to the War of 1812.