Leave Horseheads around 6:00 AM for the roughly 11–12-hour drive to Gays Mills, following Route 17/I-86 west to I-90, then across Wisconsin via I-94 and I-90. Plan fuel, rest, and meal stops around Buffalo/Rochester and again in western Wisconsin; it is a long haul, so rotating drivers and keeping the final stretch flexible will make the arrival easier. Expect tolls or fuel costs to vary by route, with approximately $120–180 in fuel depending on your vehicle. Before leaving, confirm your lodging’s check-in and parking arrangements—Gays Mills is small, and late-arrival options can be limited.
After checking in and unpacking, head toward the Kickapoo River for a gentle 45-minute sunset walk or scenic drive along the waterfront. The river is especially peaceful in the evening, with wooded bluffs and quiet roads rather than formal attractions, so bring a flashlight if dusk comes quickly. If it is still serving, stop at Kickapoo Coffee for a coffee or light bite—allow about $5–15 per person and check same-day hours, since small-town cafés may close early or operate limited midweek schedules. Then wander through the Gays Mills Apple Festival grounds and village center for 45–60 minutes; the compact streets and river surroundings are pleasant for stretching your legs, though the Apple Festival itself is seasonal and will not necessarily be taking place on this date.
Finish with a relaxed supper at a well-reviewed family restaurant or tavern in Gays Mills or nearby Coon Valley, budgeting roughly $15–30 per person. Call ahead before driving over, particularly on a Wednesday evening, as rural restaurants often have limited hours or kitchen cutoffs. Keep the night low-key after the cross-state drive; tomorrow is better suited to exploring the surrounding Driftless Area.
Start at the Gays Mills Farmers Market in the village center, allowing about an hour to browse seasonal produce, baked goods, preserves, and local crafts. Market hours can vary by season and weekday, so confirm the 2026 schedule before setting out; bring cash, although some vendors may accept cards. From there, drive roughly 25 minutes north to Kickapoo Valley Reserve near La Farge. Give yourself two to three hours for an easy trail walk or scenic drive through the wooded valleys and sandstone bluffs. Cell service is patchy, so download maps beforehand, carry water, and check trail conditions at the reserve office or website before choosing a route.
Continue about 20 minutes south to Driftless Brewing Company in Soldiers Grove for a relaxed lunch and locally brewed beer. Budget approximately $15–30 per person and allow 60–90 minutes; confirm kitchen and taproom hours, particularly if this falls outside the busier weekend period. After lunch, the drive to Wyalusing State Park near Prairie du Chien takes around 45–55 minutes. Spend 1½–2 hours at the overlooks and short walks above the Mississippi and Wisconsin Rivers. A Wisconsin state park vehicle admission is required, and the best views are reached by car between overlooks rather than by trying to cover the entire park on foot.
Finish in Prairie du Chien with the 1½-hour visit to Villa Louis, whose restored Victorian mansion and grounds offer a useful glimpse into the region’s 19th-century river-town history. Check tour times before arriving; the site is generally a daytime attraction with seasonal hours, and admission is typically in the low-to-mid teens for adults. To make the full return to Horseheads in one day, leave Prairie du Chien by about 3:00 PM—or earlier if you want all five stops—using US-18 toward I-90, then I-86/NY-17 east. It is an approximately 11–12-hour drive, so plan fuel and meal breaks in advance and confirm that your lodging or final arrival arrangements in Horseheads can accommodate a late-night arrival.