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Four music festivals to put on your calendar

From lakeshore festivals in Chicago and Milwaukee to a celebration of ragtime in small-town Missouri, here are some fests you shouldn’t miss.

Chicago Blues Festival
Chicago Blues Festival (Credit: Illinois Office of Tourism)

Whether you’re craving a crowded country music fest, want to attend the world’s largest music festival or are looking to learn about a titan of American music, you’ll find lots of options in Mississippi River Country. Here are four festivals worth seeking out.

WE Fest

Way up in the wilds of northwestern Minnesota—about three and a half hours from the Twin Cities and an hour east of Fargo—the city of Detroit Lakes (population 9,000+) welcomes more than 150,000 country music fans to town every August. We Fest, which started in 1983, calls itself the largest country festival in America and it gets the lineups to prove it—past headliners have included Carrie Underwood, Chris Stapleton, Miranda Lambert and country music icons like Willie Nelson and Dolly Parton.


Billed as “the world’s largest music festival,” Summerfest welcomes more than 800 bands and nearly 1 million fans to Henry Maier Festival Park on the shores of Lake Michigan in Milwaukee, Wisconsin. The annual festival, which celebrated its 50th anniversary in 2018, runs for 11 days on either side of the Fourth of July, and headliners perform on 11 different stages including a separate amphitheater for main acts. Don’t miss the “Big Bang” fireworks show on the festival’s opening night.

Chicago Blues Festival

Celebrate the Windy City’s contributions to America’s blues past and present at Chicago’s largest music festival. More than half a million music fans flock to Millennium Park in downtown Chicago—just blocks from Lake Michigan—every June to enjoy live performances from some of blues music’s most notable names, from Buddy Guy to Shemeika Copeland. Music starts at 11am daily on side stages, with headliners stepping into the spotlight at the park’s Jay Pritzker Pavilion from 5 to 9pm. And be sure to check out the festival’s “Blues Village,” which features more intimate performance spaces and booths from major blues labels.

Scott Joplin Ragtime Festival

Learn about Missouri’s famous son—“the King of Ragtime”—and see modern-day practitioners of his music at this annual festival in Sedalia in west-central Missouri. (Joplin lived in Sedalia in the late 1890s, where he published music, played in the Queen City Concert Band, and gave piano lessons.) The festival is held at several locations throughout Sedalia, with both free and paid venues.

Other festivals for music fans:

  • Ravinia Festival: Not a weekend festival but a summer-long series of concerts, Ravinia Festival–which takes places in the northern Chicago suburb Highland Park– is the oldest outdoor music festival in the United States, welcoming a collection of jazz, classical and pop performers at an open-air pavilion since 1905
  • Pitchfork Festival: Want to know about the coolest new acts? Head to this annual festival, organized by online tastemaker Pitchfork Media, that brings dozens of acts to Chicago’s Union Park
  • Lollapalooza: Grant Park on the shores of Lake Michigan in Chicago is the home of this popular four-day music fest held in late July and early August
  • Chicago Jazz Festival: Every September, Millennium Park hosts this annual four-day celebration of jazz music; admission is free to everyone
  • Silver Dollar City festivals: Branson, Missouri, is the entertainment capital of the Ozarks, and the Silver Dollar City amusement park hosts several music festivals throughout the year, including Country Music Days and the Southern Gospel Picnic
  • Roots N Blues Festival: Head to Columbia, Missouri—smack dab between St. Louis and Kansas City—in September to hear some of the best roots, blues and Americana performers in the country; past headliners include Jason Isbell, Lucinda Williams, Emmylou Harris and Taj Mahal
  • Big Muddy Blues Festival: St. Louis’ historic Laclede’s Landing—on the western banks of the Mississippi River—welcomes 60,000 blues fans to this fun festival on Labor Day weekend
  • Boulevardia: This unique beer, food and music festival brings headliners, delicious craft beer and tasty food to Kansas City, Missouri, every June