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  • John Prine Playing Guitar
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John Prine, Ernest Hemingway & Frank Lloyd Wright take a ride in the Park Tour

Enjoy music, architecture, literature and nature

Nothing beats a summer bike ride through the beautiful and wide open villages of Oak Park and River Forest, bounded by Thatcher woods and Forest preserves.  That is, unless you combine it with amazing music from one of the best folk singer/songwriters in the country, the late John Prine and mash up with the writings of Ernest Hemingway and architectural genius of Frank Lloyd Wright. This tour allows you to stretch your legs, enjoy the freedom of the quiet neighborhood streets by bicycle. 

If you’re craving nature, beautiful homes, and amazing music to boot, this rideabout will push all of those buttons.

Bobby’s Bike Hike’s Rideabout Series

Bobby’s Bike Hike offers our Rideabout Series of one-of-a-kind, homegrown Chicago bicycle experiences crafted for Chicagoans, by Chicagoans.

Specially designed to give locals an opportunity to get out safely and enjoy Chicago in small, socially-distanced groups, our Rideabouts celebrate the sports, music, and culture of our great city from a distinctly local perspective. 

Book early, as our maximum capacity is eight guests to preserve social distance and safety. We also offer “squad pricing” to reserve a tour for just your own small group or family. 

Improved Safety Protocols 

From our inception in 2002, health has always been a central tenet of Bobby’s Bike Hike. Bikes let you experience Chicago in a heart-healthy, environmentally-friendly way. Now we’ve developed the Bobby’s Bike Hike Rideabout Series, a bike experience for Chicagoans with today’s health considerations in mind. These rideabouts are a way to get out outside and safely celebrate the sports, music, and culture of Chicago from a local perspective. All rideabouts are capped at 9 people to keep the group small, and traversing on bikes inherently maintains safe physical distance while facilitating a communal experience. Check out our various offerings such as our 80’s in Chicago Rideabout (80s dress up encouraged!), Rideabout to Wrigley, and John Prine, Ernest Hemingway & Frank Lloyd Wright take a ride in the Park tour . We also offer special “squad pricing” to reserve a tour for just your own small group or family!

Introducing Squad Pricing

We are offering our new “squad pricing” to reserve a tour for just your own small group, company or family!  Squad pricing allows you to create your own private tour for your group, which ensures you are surrounded only by those most close to you.  Squad pricing includes up to 9 participants, includes 15% gratuity for your guide (although you’re welcome to provide more if you’d like), one parking spot one block from our downtown location.   So everything is super easy and makes the booking process stress free and easy.  If your group is more than 9 people, no worries, we can discuss that and separate your group into different groups running either at the same time or at different times, however you prefer.  Squad pricing is meant to be easy and get your group together with little effort in planning.

What To Expect

Prine’s Boyhood home (Maywood): Located just west of Chicago, along the west bank of the Des Plaines River and with the Chicago Northwestern Railroad running almost through the center, Maywood is the boyhood home of John Prine.  We’ll visit his former home and see the gritty surroundings that shaped his songwriting.

Proviso East High School: Formerly Proviso Township High School, it was during his time here that Prine started playing guitar at age 14, taught to him by his brother, David. After High School, John would become a mail carrier with a route in neighboring Westchester.  During his routes, he would start forming the lyrics to many of his now famous songs.

Frank Lloyd Wright Architecture: Frank Lloyd Wright founded his architectural practice in Oak Park, a quiet, semi-rural village on the Western edges of Chicago. It was at his Oak Park Studio during the first decade of the twentieth century that Wright pioneered a bold new approach to domestic architecture, the Prairie style. Inspired by the broad, flat landscape of America’s Midwest, the Prairie style was the first uniquely American architectural style of what has been called “the American Century.”

Ernest Hemingway’s boyhood home: Hemingway was raised in Oak Park, where is home is still visited today. Hemingway became an American journalist, novelist, short-story writer, and sportsman. His economical and understated style—which he termed the iceberg theory—had a strong influence on 20th-century fiction, while his adventurous lifestyle and his public image brought him admiration from later generations. Hemingway won the Nobel Prize in literature in 1954 for The Old Man and the Sea.

Villages of Oak Park and River Forest – Wide, tree-lined and shaded streets give way to stunning and architecturally significant homes.  These communities feel like an extension of the neighboring forest preserves that border just to the west. River Forest enjoys opulent and luxurious homes on wide lots and boasts two beautiful universities, while Oak Park provides stunning architecture and a vibrant and unique downtown.

John Prine music along the way: Widely cited as one of the most influential songwriters of his generation, Prine was known for humorous lyrics about love, life, and current events, as well as serious songs with social commentary and songs that recollect melancholy tales from his life.

John Prine Playing Folk MusicErnest Hemingway historic home tour Chicago
Frank Lloyd Wright Architectural Tour in Chicago with Bobby's Bike HikeChicago Folk Music Tour
Portrait of Ernest HemingwayFrank Lloyd Wright Architecture Tour with Bobby's Bike Hike
Chair and Guitar for Folk TourJohn Prine's childhood home tour Chicago

What Our Customers Are Saying “A John Prine fans dream with a beautiful ride through Frank Lloyd Wright’s architecture and Hemingway to boot. This tour was just what we needed to get out of the City and get some fresh air, nature.  Thank you!”

– Maura G Chicago, IL

John Prine, Ernest Hemingway & Frank Lloyd Wright take a ride in the Park Tour

Duration: 3 to 3.5 hours
Length: 10mi/17km
Level: Easy
Schedule: 1pm Mon, Wed, Fri, Sat & Sun
Age: 1+

(Discount Online Rate includes Bike)

Adults 39.99
Youth (ages 4-11) $29.99
Infant (ages 0-3) $9.99
Squad Pricing: Private Group up to 9 people) $249.99


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