It’s finally here – Milwaukee festival season!  And, that means it’s time to pull out those calendars, and start planning out all of the fun ways you’re going to spend your summer in Milwaukee.  We’re kicking off the season strong with an event, live music or festival nearly every weekend! Of course, with so much excitement gearing up, it can be overwhelming keeping track of it all.  So, we’ve put together some of our top picks for June. 

Things to Do in Milwaukee in June

Highland Games/Scottish Fest

When:  June 2nd

Where:  Hart Park

Celebrate Scottish traditions, and start June off on a high note with the Highland Games.  There will be bagpipe bands, authentic food, dancing, sheepdogs, games like the hammer throw and the caber toss, and much more.

Milwaukee Makers Market

When:  Every third Sunday

Where:  Colectivo in Bay View

The Milwaukee Makers Market is the perfect seasonal stop for the crafty hobbyist!   Whether you’re looking for your new favorite living room conversation piece or just some artistic inspiration, this market has it all.  It meets every third Sunday of the month at the Colectivo location in Bay View, with an additional opening on June 1st for Bay View Gallery Night.  

Jazz in the Park

When:  May 31st – August 30th

Where:  Cathedral Square Park

Every Thursday from 6 – 9 p.m. (and a happy hour starting at 5 p.m.), Cathedral Square Park will fill with the sounds of summer.  Drinks will be available throughout various festival tents as you enjoy the summer concert series. The musical lineup will be varied, spanning across genres and across the globe, from American classics, to funk, Cuban, brass bands, soul, reggae and Latin blues.

Brewtown Rumble

When:  June 3rd from 11 a.m. to 5 p.m.

Where:  Fuel Cafe in Walker’s Point

Milwaukee’s free ride-in vintage motorcycle festival is ready to rev up the streets of Cream City.  Now in its fourth year, this event is moving from the former Pabst Brewery over to Walker’s Point and Fuel Cafe on S. 5th St.  There will be live music, a pin-up show, vendors and, of course, awesome street bikes.

Chill on the Hill

When:  June 5th – August 28th

Where:  Humboldt Park

A Bay View favorite, Chill on the Hill will welcome more than 20 bands over the course of the summer, as well as food vendors from popular community eateries and partners.   And, this year, in celebration of the 50th anniversary of the Kids from Wisconsin tour, there will be a special show on June 22.


When:  June 7th – 10th

Where:  Henry Maier Festival Park

Milwaukee is home of the nation’s largest LGBT festival, PrideFest.  This year’s event will be even bigger as it expands into a fourth day.  The kick-off party on June 7th will feature EDM trio Cash Cash as well as other local entertainment.  Then, celebrate the rest of PrideFest with live music performances, youth mixers, drag shows, the inaugural motorcycle Pride Ride on Saturday, the Milwaukee Pride Parade on Sunday and so much more.

Wisconsin Beer Lovers Festival

When:  June 16th

Where:  Bayshore Town Center

Beer lovers, this one’s a can’t miss!  Glendale’s Bayshore Town Center will host dozens of local breweries offering samples upon samples of Wisconsin beer.  Local cheesemakers and restaurants will also be around to offer all kinds of delicious samples of their own.

Greek Fest

When:  June 22nd – 24th

Where:  Wisconsin State Fair Park

Celebrating more than 50 years, Milwaukeeans just can’t get enough the Greek festival!  With tasty gyros, lamb, chicken roasted on a spit, carnival rides and all around family fun, it’s not hard to see why.

Summer Soulstice

When:  June 23rd  

Where:  East North Avenue

Celebrate the summer solstice Milwaukee-style!  This event is one of the largest free showcases for the region’s top musical acts, visual artists, local chefs, creation stations and more.   

Cedarburg Strawberry Festival

When:  June 23rd – 24th

Where:  Historic Downtown Cedarburg

Summertime means deliciously juicy, fresh berries!  And, nothing celebrates the berry more than the strawberry!  So, come out and sample some strawberry blush wine, chicken strawberry wraps, strawberry pancakes, or get your sugar rush on with the strawberry shortcake eating competition and strawberry bubblegum blowing contest.  Any strawberry craving you might have can and will be met after you’re finished with this festival! There will also be live music, pony rides, a petting zoo and the CedarQuacker 500 where 500 rubber duckies will be released into a creek.

Planning a Visit to Milwaukee

Whether you’re coming for a day or a week, traveling alone or in a group, there’s no better place to stay than right here with us a Kinn Guesthouse. Be sure to stop by our booking page for current rates and availability. As always, we offer a “best price” guarantee when you book directly with us!