Ride with Leinie Celebrates 15 Years of Cycling, Community, and Northwoods Adventure
For 15 years, cyclists have gathered in Wisconsin’s Northwoods for an event that blends scenic beauty, camaraderie, and a healthy dose of fun. On Saturday, July 25, 2026, Ride with Leinie returns to Conover to celebrate its 15th anniversary, welcoming riders from across the Midwest to experience one of northern Wisconsin’s premier cycling events.
Hosted by the Great Headwaters Trails Foundation (GHTF), Ride with Leinie has grown into a beloved summer tradition, combining exceptional riding with a mission to expand safe bicycling and walking opportunities throughout eastern Vilas County.
At the heart of the event is Dick Leinenkugel, longtime cycling advocate and past president of Leinenkugel Brewing Company, whose passion for cycling and the Northwoods has helped shape Ride with Leinie since its early years. Dick will once again welcome riders to Conover and lead one of the event’s most popular options—a scenic trail ride on the Conover-Phelps Trail.
Whether riders are seeking a challenge or a leisurely day on two wheels, Ride with Leinie offers something for every riding style and ability level. Participants can choose from five route options, including 62-mile (metric century), 40-mile, and 20-mile road rides that wind through the scenic communities of Conover, Land O’Lakes, and Phelps. Along the way, cyclists experience quiet roads, towering pine forests, sparkling lakes, and the rolling terrain that makes Northwoods riding unforgettable.
For those who prefer a car-free experience, riders can join Dick Leinenkugel on a 20.4-mile trail ride or opt for a shorter 10.2-mile out-and-back route along the picturesque Conover-Phelps Trail. The hardpacked limestone trail offers a relaxed pace through forests, wetlands, and some of the region’s most scenic landscapes.
But Ride with Leinie is about more than the miles.
After the ride, cyclists gather for festive post-ride celebrations featuring a picnic-style lunch, beer tasting, music, raffles, and an energetic auction that has become a highlight of the day. It’s an opportunity to relax, reconnect with fellow riders, and celebrate another successful ride in true Northwoods fashion.
Most importantly, every mile ridden supports a larger mission.
Proceeds from Ride with Leinie benefit the Great Headwaters Trails Foundation and its work to develop and enhance bicycle and pedestrian trails throughout eastern Vilas County. In 2021, GHTF completed the 10.4-mile Conover-Phelps Trail—now the centerpiece of Ride with Leinie and a valued recreational asset for residents and visitors alike.
Today, the organization is focused on expanding access and connectivity. Plans are underway for a two-mile paved extension of the Conover-Phelps Trail, creating a safer bicycle and pedestrian connection to Torch Lake County Park Campground just south of Conover.
At the same time, GHTF is advancing efforts to connect eastern Vilas County communities to the nationally recognized Heart of Vilas County Bike Trail System. Work is underway to develop a 10-mile trail linking Eagle River and Saint Germain, helping create safer regional connections for cyclists and pedestrians while strengthening outdoor recreation opportunities in the Northwoods.
Fundraising events such as Ride with Leinie and GHTF’s fall SepTimber Ride in Eagle River play a critical role in turning these trail visions into reality.
As cycling tourism continues to grow across Wisconsin, investments in trail infrastructure are increasingly important to local economies, community health, and quality of life. Events like Ride with Leinie not only bring cyclists to the Northwoods, but also help create the trails and connections that keep people riding long after the event ends.
Fifteen years after its founding, Ride with Leinie remains true to its roots: great riding, welcoming community, breathtaking scenery, and a shared commitment to growing cycling opportunities in Wisconsin.
For cyclists looking to experience the very best of the Northwoods this summer, July 25 offers the perfect excuse to head north, hop on a bike, and Ride with Leinie.
For more information or to register, visit ghtrails.org/ridewithleinie. Early registration discounts are available through June 25.
Bike Fed Supporters Receive a Special Registration Discount!
Ride with Leinie organizers are graciously offering a $10 registration discount to current Wisconsin Bike Fed supporters through June 25, 2026!
- Supporters who are eligible for the discount last received an email on April 2, 2026 with the exclusive code to enter during registration.
- Supporters who have not received an email communication with discount information, as well as new supporters who donate $50 or more, may contact the Donor Relations Team at donorservices@wisconsinbikefed.org or 414-626-1540 for questions and the codes.
Please note: discount codes may not be shared, transferred, or used to register others.