MidwestWeekends.com — Your Travel Guide to the Upper Midwest
ornament
Calendar view | List view
ornament
May 2020  June 2020 July 2020
Sun
7
-
Fri
5

Blues Festival

Chicago, IL

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

Sat
6

Reggae Fest

Trempealeau, WI

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

Wed
10

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.

Sun
14
-
Thu
11

Mount Horeb Summer Frolic

Mount Horeb, WI

Just west of Madison, this town celebrates with a bean-bag toss, dog show, volleyball, craft-beer tent, Saturday fireworks and Sunday parade. 

 

Sat
13
-
Fri
12

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.

Sun
14
-
Fri
12

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.

Sun
14
-
Sat
13

Steamboat Days

Burlington, IA

There's a carnival, music on two stages, a parade Saturday and a Sunday art fair on Snake Alley.

 

Sun
21
-
Wed
17

Ice Cream Days

Le Mars, IA

The festival in this northwest Iowa town, home of Blue Bunny ice cream, includes an art fair, old-fashioned children's games, architectural tours, a polo match, airplane and helicopter stunts and a parade at 9 a.m. Saturday. And the ice cream is free.

Sat
20
-
Fri
19

Monroe Balloon Rally

Monroe, WI

There will be balloon glows and flights, weather permitting, as well as blues bands, a car show and an arts and crafts fair.

Sun
21
-
Fri
19

Wooden Boat Show and Summer Solstice Festival

Grand Marais, MN

The harbor-side North House Folk School on Lake Superior kicks off summer with a boat parade, dancing, craft demonstrations, mini-courses and a solstice parade.

In 2020, the event is online.

Sat
20

Great Lakes Pirate Festival

Mackinaw City, MI

This city on the Mackinac Straits marks the launch of the pirate ship Good Fortune with music, pirate trivia, costume and "talk like a pirate'' contests and an evening cruise under the Mackinac Bridge (tickets are 2-for-1 if you're dressed like a pirate).

Sat
27
-
Thu
25

Twin Cities Jazz Festival

St. Paul, MN

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

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.

Sat
27
-
Fri
26

Midwest Viking/Scandinavian Hjemkomst Festival

Moorhead, MN

This festival at the Hjemkomst Center includes demonstrations, performances and goods that tell about society and culture in Viking-age Scandinavia and beyond.

Sun
28
-
Fri
26

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.

Sat
27

International Bridge Walk

Sault Ste. Marie, MI

Walk across the St. Mary's River to Canada at 9:30 a.m. or ride a bike there and back between 8:30 and 9:30 a.m.

Walkers can take a bus back from Sault Ste. Marie, Ont., for $5 and must bring a passport. Otherwise, the event is free.

Sun
28
-
Sat
27

Afton Strawberry Festival

Afton, MN

This village on the St. Croix River offers an art fair, music, games, raptor demos and a strawberry shortcake-eating contest.