A Local Cyclist’s Insider Guide to Exploring on Two Wheels
By Taylor Housemen, Owner Okoboji Cyclist
Discover the best cycling trails in Okoboji. Scenic loops, local rides, events, and insider tips await in this hidden Midwest cycling gem.
Imagine the feeling of the wind against your face as you pedal along the edge of crystal-clear lakes, with the sun casting golden rays across the water. This isn’t just a bike ride – this is Okoboji, where cycling becomes an experience, and the trails? They’re the hidden treasure only those on two wheels (or maybe 3) truly get to enjoy.
Trail Variety for Every Type of Rider
The Okoboji area offers a dream mix of paved routes, scenic loops, and adventurous paths. Whether you’re a casual weekend rider or a hardcore cycling enthusiast, these trails have a way of pulling you in and making each ride feel like an exploration.
From quiet countryside cruises to trails winding past wild prairies and glittering water, every route has its own charm—and locals know them like the back of their handlebars.
“We have been here at the lakes area for over 50 years, and we have watched the progress and changes that have happened throughout the years. The incredible expansion of the trail system, and the amazing generosity the community has shown to make these visions happen is just unlike anywhere else. If you haven’t seen Okoboji by bike, you haven’t truly experienced Okoboji.”
— Paula Richter, The Three Sons
Local Cycling Events That Bring the Community Together
Cyclists look forward to several must-do events throughout the seasons. These rides often offer a unique and fun way for locals and visitors to enjoy the area trails while fundraising for their continued expansion.
Save the dates for these annual events:
- University of Okoboji Campus Classic (last weekend in June)
- BRASL Ride (second Saturday in July)
- U of O Homecoming Triathlon (third Saturday in July)
- University of Okoboji Oktoberfest (last Saturday in September)
- Sportsman’s Tiki Ride (first Saturday in August)
These rides combine fun, fitness, and community connection—whether you’re racing for time or just enjoying the ride.
Fan-Favorite Cycling Trails in Okoboji
The Spine Trail
Stretching over 40 miles, the Spine Trail is the backbone of the Iowa Great Lakes trail system. It glides through lakefronts and towns with scenic views and smooth pavement, perfect for a relaxing ride or a full day in the saddle.
Kenue Park and Hogsback Trails
Want a wilder ride? These gravel and nature trails weave through wetlands and prairie habitat—ideal for birdwatching, adventure seekers, or those who love to ride immersed in nature’s soundtrack.
West Okoboji Trail Loop
An all-day experience that blends small-town charm with lakeside scenery, this loop offers stops at docks, cafés, and picnic spots. It’s the Okoboji region at its best—on two wheels.
Tatanka Ska Trail to Lake Park
The newest gem: 12 paved miles (one way) from Spirit Lake to Lake Park. Riders pass farm fields, rivers, wetlands, and end at a cozy coffee shop—the perfect mid-ride reward before pedaling back.
For Roadies
Prefer pavement? The area offers low-traffic, flat, and fast county roads perfect for training or cruising. Download the Strava app or link up with a local group ride—routes from 20 to 100 miles await.
The opportunities for new and unique rides are endless! With over 40 miles of paved trails and connections to surrounding towns, you’re sure to find adventure around every twist and turn on the cycling trails in Okoboji. Make sure to check out the Dickinson County Trails Map before you plan your ride!
The Magic of the Journey: Little Surprises Along the Way
What really makes the Okoboji cycling experience unforgettable? The unexpected.
“I remember one summer morning, while riding the Spine Trail, a group of us stopped at a clearing where someone had set up a pop-up lemonade stand just for cyclists. Ice-cold drinks, laughter, and great conversation—it’s those simple joys that make this place so memorable.”
– A happy cyclist on an Okoboji trail
From wildlife sightings to hidden cafés and trail-side chats with locals, these surprises on the cycling trails in Okoboji make each ride feel fresh, even if it’s one you’ve done a dozen times before.
Four Seasons of Two-Wheeled Adventure
Think biking in Okoboji is just for summer? Think again. Each season paints the cycling trails in Okoboji in a different light:
- Spring: Budding wildflowers and baby animals popping up all around.
- Summer: Sunny skies, lake dips, and Nutty Bars post-ride.
- Fall: Bursts of color, crisp air, and peaceful roads.
- Winter: Snow-dusted trails for fat biking and cross-country skiing.
Yes, winter cycling is a thing here—and it’s beautiful.
The Okoboji Cyclist: The Heartbeat of the Local Scene
At the center of Okoboji’s cycling culture is The Okoboji Cyclist, a local bike shop known far beyond the lakes. It’s the go-to for repairs, rentals, group rides, and gear—whether you’re a pro or first-timer.
Stop in to their Milford or Spirit Lake locations found right on main street for insider tips and all your cycling needs while adventuring through the Iowa Great Lakes.
Make Okoboji Your Next Cycling Destination
So why ride here?
Because the cycling trails in Okoboji aren’t just routes—they’re experiences. They’re filled with heart, beauty, and community, making every ride more than just exercise. Whether you’re tackling 60 miles with your cycling club or sipping coffee in Lake Park mid-ride, this is a place where memories are made on two wheels.
So gear up, roll out, and discover why Okoboji is the hidden gem of Midwest cycling.