Madison, Wisconsin, has an uncanny way of feeling small and neighborly while hosting a metro population of nearly 700,000. Its accessibility is due, in part, to its being one of only two major cities in the U.S. situated on an isthmus — a strip of land between two bodies of water — so it's easy to cross from one side of downtown to the other in just a few minutes. Residents take immense pride in where they live, as the city is home to more than 140 neighborhood associations. Deemed the "Biking Capital
of the Midwest," it also happens to be one of the most accessible cities in the region for cycling.
The League of American Bicyclists awarded Madison a coveted Platinum status in 2015, recognizing it as one of the best cities for biking in the country. And it's still going strong as the only community with this ranking east of the Mississippi River (not to mention that it's also a hub for unicyclists!). Sandwiched between the beautiful and historic lakes of Mendota and Monona, Madison shouldn't be missed if you're looking for one of America's best college towns for a scenic weekend full of fun.
From the iconic Wisconsin State Capitol Building to every excuse to "jump around" at the Camp Randall Stadium and the eclectic shops and restaurants along State Street, this mid-sized city is a wealth of opportunities for great food, recreation, and charming neighborhoods. State Street also happens to be a pedestrian- and bike-friendly mall, where the only motorized vehicles are city buses, so you can cruise this iconic thoroughfare and stop into local businesses, like artist-run stationary store Anthology or B-side Records, a music shop that's been in business since 1982. Then, grab lunch at a downtown classic, Mediterranean Cafe — fondly known by locals as "Med Cafe."
Read more: The 5 Best Hidden Hot Spring Hikes In California
Take In Scenic Lake Views And Urban Highlights In Madison
Madison and its suburbs contain more than 200 miles of biking and hiking trails. Don't have your own equipment? You can rent one via BCycle, the first all-electric bike-share program in the U.S. with more than 40 locations around town.
One of the most popular paths is the Monona Loop, extending nearly 12 miles around its namesake lake on the south side of downtown. You'll pass Frank Lloyd Wright's iconic Monona Terrace Community and Convention Center overlooking the water, where you can stop for panoramic views from the rooftop garden. The garden is also home to the Otis Redding Memorial, which honors the musical legend who died in a plane crash in Lake Monona in 1967. Continuing along the route, you'll find yourself at the lovely 16-acre Olbrich Botanical Gardens. Head into Madison's funky Near East Side neighborhoods and stop for a "magic hour" drink at Weary Traveler Freehouse on Williamson Street — folks usually call it "Willy Street."
On the north side of town, along Lake Mendota and around the University of Wisconsin-Madison campus, take to the Lakeshore Path for beautiful views over the water. The Lakeshore Path comprises two parts: the Howard Temin and the Lake Mendota segments. Only the 4.2-mile, paved Howard Temin trail is open for cycling, and you can enter via two primary trailheads: one near the Memorial Union on North Park Street and another at the intersection of University Bay Drive and Oxford Road. While traversing the paths, you can learn about the ancestors of the Indigenous Ho-Chunk people, who have called Lake Mendota home for thousands of years. In fact, the archeological discovery of ancient dugout canoes preserved in the lake suggests that people have been living here and fishing these waters for at least 4,500 years.
Bike Around Madison's Scenic Countryside
Make sure to visit the University of Wisconsin Arboretum, which boasts 17 miles of mixed-use paths, service roads, and boardwalks through restored natural habitats, from savannas to wetlands. Here, you'll also discover the legacy of a mysterious "lost city" in an enchanting forest along these scenic trails. This is the spot to see wildflowers in the spring, especially at Longenecker Horticultural Gardens, where lilacs, magnolias, buckeye, azaleas, and many more go on full display in the spring.
If you're in the mood to get out of town for the day, there's no shortage of scenic and inspiring routes through the surrounding countryside and the Driftless Area. The Taliesin Loop is a favorite for Frank Lloyd Wright fans, starting at the acclaimed architect's home and studio in Spring Green. From here, you're also only about a 30-minute ride from House on the Rock, another phenomenal — and quirky! — Wisconsin architectural gem. Seeking a challenge? Madison's 112-mile Ironman Double-Loop is a competitor's dream, running through central Madison and the scenic, rural west side of the city. Wisconsin also happens to be home to America's first rail to trail route, a hiker and biker haven through scenic forests, just about two hours northwest of Madison in Sparta.
After you've cruised along miles of scenic trails, cozy up at one of the city's many recognizable chain hotels or, for something more unique, check into The Speckled Hen Inn Bed and Breakfast, a 2025 Tripadvisor Traveler's Choice award recipient thanks to its comfy accommodations, inviting farm location with friendly animals, and easy proximity to both downtown and Dane County Regional Airport.
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