MidwestWeekends.com — Your Travel Guide to the Upper Midwest

Music festivals 2020

January

  • (Jan. 30 – Feb 1)Winter Dance Party

    Clear Lake, IA

    The Surf Ballroom marks the 61st anniversary of the plane crash that killed Buddy Holly, with concerts, luncheons, dance lessons and crash-site tours.


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 16 – 24)Duluth Dylan Festival

    Duluth, MN

    The town in which Bob Dylan was born celebrates the singer's 79th birthday with a Blood on the Tracks train ride, a singer-songwriter contest, a bus tour, films, music and a trivia contest.

    The festival is exclusively online in 2020.


  • (May 21 – 25)North Iowa Band Festival

    Mason City, IA

    There's a carnival, craft show and car cruise, but don't miss the 10 a.m. Saturday band parade in this northern Iowa town, which Meredith Willson made famous in "The Music Man.''


  • (May 22 – 24)World's Largest Brat Fest

    Madison, WI

    There's music on four stages, plus kids' games, a sports zone, carnival rides and Sunday fireworks. Headliners include Smash Mouth. Admission is free. Outside the Alliant Energy Center.


  • (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 – 13)Stamman Scandinavian Folk Festival

    Nisswa, MN

    This festival in the Brainerd Lakes area features visiting musicians from Denmark, Sweden and Norway as well as many North American folk musicians.


  • (Jun 12 – 14)Ribfest Chicago

    Chicago, IL

    This street festival in the Northcenter neighborhood, on Lincoln Avenue between Irving Park Road and Warner Avenue, features barbecue plus indie, roots, rock and alt country music.

    There's a Kids Square with games and a rib-eating contest Friday with professional eaters.


  • (Jun 12 – 13)Winstock Country Festival

    Winsted, MN

    Luke Combs and Darius Rucker headline this festival just west of Minneapolis.


  • (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 13)PorchFest

    Mount Morris, IL

    During this afternoon music festival, 19 bands perform for 45 minutes each on porches around town. There will be food vendors, too.


  • (Jun 19 – 20)Northwoods Blues Festival

    Chippewa Falls, WI

    The blues festival is at Chippewa Riverfront Park. 


  • (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 Fest

    Cadott, WI

    This year's big outdoor festival near Chippewa Falls features Thomas Rhett, Dierks Bentley and Kane Brown.


  • (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 25 – 27)Lakes Jam

    Brainerd, MN

    Brothers Osborne, Jon Pardi and Ratt are among the headliners at this music-and-camping festival at Brainerd International Raceway.


  • (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 2 – 5)National Women's Music Festival

    Middleton, WI

    In addition to concerts, this musical and cultural festival at the Marriott Madison West features comedy, theater, film and writers' workshops.


  • (Jul 2 – 5)Ribfest

    Romeoville, IL

    Headliners in this southwest Chicago suburb include REO Speedwagon and Styx in Knoch Park, where there's also magic shows, kids' games, food and fireworks on the last evening.


  • (Jul 3 – 5)Iowa City Jazz Festival

    Iowa City, IA

    This downtown festival features a Culinary Row, Fun Zone for kids and Sunday fireworks in addition to music.


  • (Jul 9 – 12)Winnipeg Folk Festival

    Winnipeg, MB

    This easy-going, family-friendly festival features more than 70 performers from eight countries, food and hand-made art from around the world plus a fun play area for children. 

    Many people camp on-site at Birds Hill Provincial Park. Tickets are cheapest when bought in advance.


  • (Jul 9 – 12)Hodag Country Festival

    Rhinelander, WI

    This year, performers at this big fest include Neal McCoy and Darius Rucker. There's a band contest, too.


  • (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 10 – 11)Basilica Block Party

    Minneapolis, MN

    Praise the Loud at this ticketed rock-music fest at the Basilica of St. Mary on the edge of downtown. 


  • (Jul 11)Driftless Music Festival

    Viroqua, WI

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


  • (Jul 16 – 18)Rock Fest

    Cadott, WI

    This year's outdoor festival near Chippewa Falls features Limp Bizkit, Slipknot and Disturbed.


  • (Jul 16 – 18)Rock USA

    Oshkosh, WI

    This rock festival is held in Ford Festival Park.


  • (Jul 16 – 18)Country Jam

    Eau Claire, WI

    Luke Combs, Chris Young and Locash are  among the headliners of this fest. There's camping on-site.


  • (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 17 – 19)Hiawatha Traditional Music Festival

    Marquette, MI

    This folk-music festival in Tourist Park also features a juried arts and crafts show and camping on-site.


  • (Jul 17 – 18)Lowertown Blues & Funk Festival

    St. Paul, MN

    This free, all-ages festival is in Mears Park.


  • (Jul 18)Bayfront Reggae & World Music Festival

    Duluth, MN

    Listen to island music on the shore of Lake Superior.


  • (Jul 19)Woodstock Folk Festival

    Woodstock, IL

    Listen to music on the square in this town just over the Wisconsin border from Lake Geneva.


  • (Jul 24 – 25)Prairie Dog Blues Festival

    Prairie du Chien, WI

    This Mississippi River festival on historic St. Feriole Island features 12 bands on two stages, with onsite camping.


  • (Jul 30 – Aug 1)Bix Beiderbecke Memorial Jazz Festival

    Davenport, IA

    Since 1972, fans of this Jazz Age cornetist and composer have held this festival in his hometown on the Mississippi.


  • (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 30 – Aug 2)Mile of Music

    Appleton, WI

    More than 180 singer-songwriters perform at more than 40 venues along College Avenue downtown.


  • (Jul 31 – Aug 2)Blues on the Chippewa

    Durand, WI

    Just up the Chippewa River from Lake Pepin, this free blues festival in Memorial Park features 16 bands.


  • (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.


  • (Jul 31 – Aug 1)Soul & Blues Festival

    Iowa City, IA

    This is the second year of this downtown music festival. 


August

  • (Aug. 6 – 9)Minnesota Bluegrass & Old-Time Music Festival

    Richmond, MN

    This 41st annual family-friendly festival includes music on five stages and workshops at El Rancho Mañana Campground, 20 miles west of St. Cloud. 


  • (Aug. 6 – 8)Ashley for the Arts music festival

    Arcadia, WI

    This nonprofit festival is in the southwest Wisconsin bluffs, half an hour north of Winona, Minn.

    Headliners include Sawyer Brown, Lynyrd Skynyrd and Switchfoot. Tickets for all three days are $15 when bought online. In addition to music, there will be a hot-air balloon launch, circus acts, car show, arts, children's activities and Saturday fireworks.


  • (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.