Frisco Highline Trail – Springfield, Missouri

Frisco Highline Trail – Springfield, Missouri

Starting from Springfield’s northwest trailhead, I rode the Frisco Highline Trail, a 35-mile rail-to-trail conversion that follows the historic Frisco Railroad. From paved sections to rugged stone, from Halloween decorations to a steady headwind, the day offered everything I love about cycling—history, landscape, and the people you meet along the way.

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Katy Trail – Rocheport, Missouri

Katy Trail – Rocheport, Missouri

My overnight at the Rocheport trailhead led to a 60-mile ride on the iconic Katy Trail—through tunnels, past river bluffs, and alongside friendly strangers. From early-morning owls to the kindness of fellow riders, the day reminded me why this 240-mile Missouri treasure is more than just a bike path—it’s a journey through time, nature, and community.

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Jewel Cave

Jewel Cave

My Black Hills day began with a Jewel Cave tour, where a ranger guided us deep into the underground world of crystals, geology, and history. From there I headed to Custer State Park, caught Kevin Costner’s Spirit of Tatanka film, and went for a bike ride past deer, pronghorn, buffalo, and a plaque about South Dakota’s first poet laureate, Charles “Badger” Clark.

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Rainy Lake Trail
Van Life, Bike Rides Greg Ott Van Life, Bike Rides Greg Ott

Rainy Lake Trail

The Rainy Lake Trail links International Falls to Voyageurs National Park, passing through historic Ranier and featuring plaques on the area’s lumberjacks, miners, and voyageurs. Along the way are landmarks like the Bronko Nagurski statue, the towering Smokey Bear, and the sprawling Boise Paper mill. The route ends with a stop at Ronning’s for coffee, licorice ice cream, and a glimpse of small-town life.

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Gitchi-Gami Bike Trail
Van Life, Bike Rides Greg Ott Van Life, Bike Rides Greg Ott

Gitchi-Gami Bike Trail

Waking up beside a massive steam locomotive in Two Harbors, Minnesota, set the tone for a day steeped in history and scenery. Agate Bay’s skyline was dominated by the towering Iron Ore Docks—over 1,300 feet long and nearly seven stories high—a powerful relic of the region’s mining heritage. Across the bay, the 1892 Two Harbors Lighthouse kept watch, still guiding ships on Lake Superior. After a coffee stop at Cedar Coffee Company, tucked away on a dirt road outside town, the day shifted to cycling the hilly Gitchi-Gami State Trail. Scenic lake views, rugged shoreline, and a chance encounter with a family bound for Vermont framed the ride, as rain clouds rolled in over Split Rock Lighthouse State Park. By evening, the rain had settled in for the night.

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Elroy-Sparta Trail, WI
Bike Rides, Van Life Greg Ott Bike Rides, Van Life Greg Ott

Elroy-Sparta Trail, WI

A long ride on the Elroy-Sparta Trail — the first rail-to-trail conversion in the U.S. — turned into a full-day adventure of tunnels, wildflowers, butterflies, and a minor crash. Along the way, travelers from around the world crossed paths, the Wisconsin landscape rolled by, and a few questions came up about the only state in the country that charges to ride its bike paths.

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Ride to Gills Rock
Bike Rides Greg Ott Bike Rides Greg Ott

Ride to Gills Rock

I rode my gravel bike from Peninsula State Park up to Gills Rock at the northern tip of Door County. The route hugged the shore of Green Bay, passing through quiet towns, wooded stretches, and scenic farm country. It was mostly a peaceful, rewarding ride with views that kept pulling me off the road to take photos.

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Cycling Madeline Island
Bike Rides, historic sites Greg Ott Bike Rides, historic sites Greg Ott

Cycling Madeline Island

I started the day in the woods near Bayfield with a maple-syrup-heavy breakfast, caught the ferry to Madeline Island, and biked 33 miles through sun, gravel, and quiet roads. Along the way, I met fellow cyclists, visited sacred Ojibwe sites, explored La Pointe, and ended the day with a black-bean burger, live music, and a sunset ferry ride back to Bayfield. Tired, dusty, and happy, I rolled back to my quiet pull-off in the woods and crashed hard.

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