Four Midwest Vacation- Worthy Rail-Trail Places
By Robert Annis
Flyover country? Not even close. Here are four Midwest vacation spots that offer abundant fun along with some awesome greenways. Milwaukee, Wisconsin Perhaps a somewhat underrated large city in the Midwest, Milwaukee boasts friendly residents, beautiful green spaces and lots of opportunities for fun, including from some truly great rail-trails. The Oak Leaf Trail (rtc.li/oak-leaf-trail) has been called the crown jewel of Milwaukee County’s “emerald necklace” park and trail system, and the description fits. The 120-mile linear park circles the city, giving riders incredible views of Lake Michigan while passing by multiple pocket parks and attractions like the Milwaukee Art Museum. One of my treasured travel memories happened when riding along the Oak Leaf: My wife Dee and I were riding our bikes on a beautiful summer afternoon that was about to give way to evening. We stopped at one of the many parks along the route and soon found ourselves at an outdoor beer garden with massive steins of beer in our hands. Sitting at a picnic table, we were serenaded by a polka band and watched a gentleman and his granddaughter dance. It’s probably been more than a decade since that bike ride, and I still smile whenever it comes to mind. The Hank Aaron State Trail (rtc.li/hank-aaron), named after Major League Baseball’s true home-run king, is another trail connected to the Oak Leaf Trail that’s worth checking out. Appropriately enough, it runs by American Family Field, where the Milwaukee Brewers play, and past the Mitchell Park Horticultural Conservatory, which displays more than 1,800 plant species from across the globe under large glass domes. One of the domes is covered in thousands of LED lights that are timed to
PHOTOS: This page: Along the Oak Leaf Trail in downtown Milwaukee, Wisconsin | Front Room Photo. Opposite page: The Monon Trail in Indiana connects to the Indiana State Fair Grounds and the Indianapolis Cultural Trail. | Robert Annis.
Rails to Trails MAGAZINE | SPRING/SUMMER 2025
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