MidwestWeekends.com — Your Travel Guide to the Upper Midwest

Music festivals 2020

February

April

  • (Apr. 17 – 19)Roots and Bluegrass Festival

    River Falls, WI

    Hear music at half a dozen venues in the downtown of this western Wisconsin college town.


  • (Apr. 24 – 25)Eau Claire Jazz Festival

    Eau Claire, WI

    Headliners play the State Theatre, and on Friday, more than 50 bands play acoustic jazz, ragtime, big-band and blues along Barstow Street downtown, recreating New York's 52nd Street.


May

  • (May 1 – 2)Midwest Music Fest

    Winona, MN

    Dozens of musical groups in all genres play in museums, galleries, cafes and arts centers across town. There are arts workshops for children, too.


  • (May 24)BobFest

    Spring Green, WI

    The Spring Green General Store in this artistic town on the Wisconsin River celebrates Bob Dylan's 79th birthday with free outdoor music.


  • (May 26 – 30)Gospel Festival

    Chicago, IL

    This free music festival is in Millennium Park and across the street at the Cultural Center.


June

  • (Jun 5 – 7)Blues Festival

    Chicago, IL

    The largest of Chicago's free music festivals draws 750,000 people to Millennium Park. 


  • (Jun 6)Reggae Fest

    Trempealeau, WI

    The Trempealeau Hotel hosts this easygoing festival on the banks of the Mississippi. 


  • (Jun 12 – 13)Steel Bridge SongFest

    Sturgeon Bay, WI

    More than 150 musicians and songwriters perform in more than 15 venues around town to benefit the historic Michigan Avenue canal bridge.


  • (Jun 12 – 14)Country Thunder Iowa Music Festival

    Forest City, IA

    The country-music festival in this town near Clear Lake features Lynyrd Skynrd, Riley Green and Old Dominion. There's camping (and glamping) onsite.


  • (Jun 25 – 27)Twin Cities Jazz Festival

    St. Paul, MN

    Listen to jazz in Mears Park, in St. Paul's Lowertown.


  • (Jun 25 – 27)Country USA

    Oshkosh, WI

    Toby Keith, Little Big Town and Thomas Rhett are among the headliners of this year's big festival at Ford Festival Park.


  • (Jun 26 – 28)Cedar Basin Jazz Festival

    Cedar Falls, IA

    There will be 42 hours of free entertainment in Sturgis Park, including a Sunday morning gospel set and a jazz brunch.


July

  • (Jul 10 – 12)Blissfest

    Cross Village, MI

    This family-friendly folk and roots festival on a farm includes reggae, country, zydeco, jazz and Celtic music on three stages and four workshop areas. There's also a juried arts and crafts fair. Rustic camping is available.


  • (Jul 10 – 12)Square Roots Festival

    Chicago, IL

    The Old Town School of Folk Music presents this Lincoln Square festival, which includes more than 60 acts on four stages plus 30 local and regional craft beers and food from neighborhood restaurants.


  • (Jul 11)Driftless Music Festival

    Viroqua, WI

    This free folk and roots festival is in Viroqua's Eckhart Park.


  • (Jul 16 – 18)Rock USA

    Oshkosh, WI

    This rock festival is held in Ford Festival Park.


  • (Jul 17 – 18)RiverSong Music Festival

    Hutchinson, MN

    This family-friendly festival on the Crow River, west of the Twin Cities, features folk, blues, jazz and other grassroots music on three stages, including one for children. There's onsite camping and food.


  • (Jul 30 – Aug 2)Lollapalooza

    Chicago, IL

    This big music festival features dozens of bands and, unlike other Grant Park festivals, is not free. Reserve rooms far in advance.


  • (Jul 31 – Aug 1)Grant Park Music Festival

    Chicago, IL

    Professional musicians, many of them world-famous, offer free classical concerts in Millennium Park's beautiful Pritzker Pavilion.

    The festival is virtual this year.


August

  • (Aug. 14 – 16)Bayfront Blues Festival

    Duluth, MN

    The 32nd annual music fest on the Lake Superior harbor showcases national and regional acts on three stages.


  • (Aug. 14 – 16)Blues, Brews & BBQ

    McHenry, IL

    Listen to the blues and eat barbecued foods in Petersen Park on McCollum Lake.


  • (Aug. 15)HarborPark Jazz & Blues Festival

    Kenosha, WI

    This free festival is in the lakefront Celebration Place.


  • (Aug. 21 – 22)Big Bull Falls Blues Fest

    Wausau, WI

    Enjoy national and local blues musicians in Fern Island Park. There's a beer garden, of course.


  • (Aug. 27 – 30)Lakes Bluegrass Festival

    Pine River, MN

    This family-friendly festival, just off the Paul Bunyan State Trail, features more than 40 bluegrass shows and free workshops.


  • (Aug. 28 – 30)Porcupine Mountains Music Festival

    Silver City, MI

    Few settings are more beautiful than Porcupine Mountains Wilderness State Park on Lake Superior; 25 national and regional blues, folk and bluegrass acts perform.

    It's canceled in 2020.


  • (Aug. 28 – 30)Great River Folk Festival

    La Crosse, WI

    This festival in Riverside Park includes children's activities, a traditional arts and crafts fair and music performances and workshops.


  • (Aug. 29 – Sep 6)Chicago Jazz Festival

    Chicago, IL

    This free festival features music at the Chicago Cultural Center and  Millennium Park.


  • (Aug. 29)Crossroads Blues Festival

    Rockford, IL

    Enjoy a day of blues in Lyran Park, with food from local restaurants.


September

  • (Sep. 4 – 6)Marquette Area Blues Fest

    Marquette, MI

    Enjoy a weekend of music in Mattson Lower Harbor Park on Lake Superior.


  • (Sep. 5 – 6)Fox Jazz Festival

    Menasha, WI

    This free Fox Cities jazz festival is in Jefferson Park, on the shores of Lake Winnebago.


  • (Sep. 6)Virtual World Music Festival

    Chicago, IL

    The festival will be presented online 1-3 p.m. on Sundays in September.

    Normally, there will be more than 80 artists performing at more than 30 venues across the city, including the Chicago Cultural Center. 


  • (Sep. 12)Virtual Radio Waves Music Festival

    Grand Marais, MN

    WTIP, North Shore Community Radio, hosts this outdoor fest of more than 25 local and regional music acts next to the municipal campground.


  • (Sep. 12 – 13)Virtual World Music Festival

    Madison, WI

    This free festival features music and dance from around the world on the Memorial Union Terrace and, on Saturday, at the Willy Street Fair.

    It's virtual this year.


  • (Sep. 25 – 26)Blue Ox Music Festival: Campout in the Pines

    Eau Claire, WI

    This family-friendly acoustic festival is near Eau Claire and features Big Wu, Pistol Whippin Party Penguins, Lindsay Lou and Buffalo Gospel.

    There's camping onsite.


  • (Sep. 26 – 27)Hyde Park Jazz Festival

    Chicago, IL

    Listen to non-stop music during this free festival at venues in and around Midway Plaisance, near the Museum of Science and Industry and Lake Michigan.

    This year, the festival is virtual on Saturday, but on Sunday there will be live music on mobile stages in Hyde Park.


October

  • (Oct. 30 – 31)Witching Hour Festival

    Iowa City, IA

    This festival focuses on the creative processes of musicians, artists, comedians, writers, thinkers, scientists and magicians.