Posted on Oct 27, 2016

Fall Riding Trips

Fall is a favorite riding season for many. The changing leaves are beautiful and it’s always tempting to get one more run in before winter. Riders are always hunting for new adventures, and having spent most of my two wheeled years in Wisconsin, I’ve been lucky enough to come across some great local ones. 

  1. Kickapoo Valley Reserve/Wildcat Mountain – Considered part of Wisconsin’s “Driftless Area,” the roads around Kickapoo Valley Reserve have something for everyone.
  2. Pewitt’s Nest – A unique nature reserve outside of Baraboo, Wisconsin. This destination offers not just great roads, but a unique natural gorge and swimming pool for the brave.
  3. Leland – One of the stops of the biannual Slimy Crud Run, the roads around Leland are sweeping, carved and scenic. After riding you can grab lunch lakeside at Schelter’s Bar and Grill.
  4. Milwaukee Lakefront– Often overlooked, Milwaukee is a great destination for gearheads. Go for a walk in Lake Park, visit the Harley Museum, dine at the Motor Bar & Restaurant, stay at the Iron Horse Hotel and visit local legends like the Fuel Café and the newly opened Royal Enfield for a taste of Milwaukee’s motorcycle culture.
  5. Holy Hill – Built in 1858, Holy Hill isn’t just a leaf-viewing vantage point and craft fair destination. Part of the 120-mile Kettle Moraine scenic drive, there are miles of walking paths to stretch your legs, and after you can refuel with bakery at the Holy Hill Café. It’s open Friday through Sunday, 9 a.m.-3 p.m. Local business Pine Hill Orchard also opens a stand just down the road from August through December, selling homemade apple pie, honey in the comb, cider and deluxe caramel apples.
  6. Door County – A popular vacation destination for many, Door County is an epicenter of small town charm and beautiful fall colors. From shopping local cherry and apple products to fish boils and winery tours, Door County is the perfect relaxed riding trip.

Two motorcycle riders

Even if you don’t live in Wisconsin, adventures are always close to home. Resources like and Wisconsin Motorcycle Roads Travel Guide are great for inspiration, and don’t forget to regularly check in with us for regular updates on riding-related tips, trips and events!