Galena, Illinois
Drive time: 2 hours 45 minutes

At the southeast tip of the Driftless Area, a rugged region in the upper Mississippi River basin that was spared glacial flattening, Galena is defined by undulating hills and river valleys: bucolic scenery that makes for epic gravel biking. Chicago transplant James Hillis of Driftless Cycling Tours can point you in the right direction with an itinerary ($50) or even guide you himself on long rides across everything from paved roads to off-road trails, including overnight stops (starting at $200). For rentals, he recommends Bicycle World in Dubuque, Iowa, just across the Mississippi. (Try a Trek drop bar bike for an intense ride; it’s $60 for half a day or $100 for a full day). Rail-to-trail conversions along the Galena River are great for beginners, while more advanced riders will want to pedal south to the rural areas of Jo Daviess County for short, steep climbs and descents.

While there See the Driftless from a new perspective on a sunrise or sunset hot-air balloon ride with Galena on the Fly, which offers a 45-minute flight that launches from Eagle Ridge Resort & Spa ($250).