Rock the Rails

From the founder of Celebrate Highwood’s ever popular Nashwood and Great Highwood Pumpkin Fest comes 28 Mile Distilling’s Rock the Rails. This first-of-its-kind music showcase celebrates the connection between independent artists and independent venues along the Metra rail line from Chicago to Kenosha; bringing you intimate performances and exclusive artist access. 28 Mile, located just steps from the Highwood train station, will feature incredible talent from across the country. From rising artists on the verge of breaking out to nationally recognized performers like Jimmie Allen, Mims, Bubba Sparxxx, and Michael Winslow, the initial Rock the Rails Music Series kicks off June 12 through the end of summer, every Friday night at 8 PM, with shows ending before the last train departs. The concept of Rock the Rails is built around original artists, authentic performances, and songs that connect audiences. 28 Mile Distilling Co. will serve as a first stop “along the rails” for artists on larger tours craving intimacy along the way that larger venues just don’t provide. From country and rock to hip-hop and high-energy entertainment, every Friday night will deliver a one-of-a-kind experience just steps from the Metra line at 28 Mile Distilling Co. Below is the full summer Friday Night 2026 Rock the Rails schedule: Note: all shows begin at 8 PM June 12: Rising country artist and gifted storyteller Kelly Daniels brings his blue-collar authenticity to 28 Mile. June 19: Making waves from Cincinnati to Nashville, Blake Tyler is a former college athlete turned country artist with over 250,000 monthly listeners on Spotify. July 10: Chase-N-Tyler, a dynamic country-duo brings a grunge “in your face” type performance to enthrall any listener. July 17: Traditional country singer and songwriter Alex Key writes all his own songs and drives his own tour bus to bring his classic country sound (heavy on pedal steel and fiddles!) July 24: Rapper MIMS, best known for his chart topper “This is why I’m Hot” joins the Rock the Rails line up with a special with bourbon launch! July 31: Country double bill Kendal Tucker and Carson Lee bring their love of all genres into their country vibe. August 7: Rapper Bubba Sparxxx, known for his chart-topping singles “Ugly” and “Ms. New Booty,” brings critically acclaimed sound to the 28 Mile stage. August 14: Michael Winslow, godfather of Beatbox and famous for his roles in Cheech and Chong, Spaceballs, and Police Academy, brings a show of comedy and music to the stage. August 21: Country Music Association’s New Artist of the Year in 2021, Jimmie Allen’s genre bending performance honors country’s storytelling while leaning into today’s pop-forward energy. August 28: Country/southern rock darling Erin Stroll brings her authentic storytelling and electrifying stage presence to Highwood, as the last stop on the summer Rock the Rails tour.

Event Links

Website: https://go.evvnt.com/3679369-0

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