Milwaukee Skyline

Summer in Milwaukee: A City of Festivals and Fun in the Sun

If you’ve heard the Milwaukee area referred to as the “City of Festivals,” there’s a good reason for it. From the Lakefront Festival of Art and the Milwaukee Film Festival in spring to the plethora of Milwaukee summer festivals such as German Fest, Irish Fest, and Festival Italia, we have festivals for just about everything.

However, the summer fun in Milwaukee is not limited to festivals and outdoor events. Eastcastle Place is located near the beautiful Lake Michigan lakefront and in the heart of the Greater Milwaukee area.

Our residents are within walking distance or a short ride from Bradford Beach, Lakeshore State Park, the Milwaukee Art Museum, and many other Milwaukee attractions. Additionally, our many parks, walkable downtown, and Historic Third Ward neighborhood promise plenty of things to do in Milwaukee this summer.

We’re looking forward to sharing our insider’s guide to the 2024 Summerfest Lineup, as well as our summer selection of fun things to do inside and outside in Milwaukee. Read on to find out more about what summer in Milwaukee is like. There are plenty of opportunities for live music, local experiences, food, drinks, and fun in the sun.

2024 Summerfest Lineup:

Summerfest always delivers when it comes to a mixture of new, upcoming musical artists and classic, long-established greats. Concertgoers can expect to hear a wide range of musical genres.

Whether you join the crowd to hear The Box Tops perform “The Letter,” Amy Grant sing “Baby, Baby,” or are looking forward to a fair share of jazz, blues, and country, there’s something for everyone with this year’s lineup.

The 2024 lineup also offers entertainment for the whole family and all ages. If you have the grandkids with you, check out Bob Bohm’s Comedy Magic Show. It is no wonder touring musicians call Summerfest the “Big Gig.” While this year’s performers number over 150, here are some select acts you will want to mark on your calendar and buy tickets for you will not want to miss.

Summerfest show nights include June 20th – 22nd, June 27th – 29th, and July 4th – 6th. Attendees can expect a great view of the fireworks over Lake Michigan on July 4!

For the official Summerfest 2024 Lineup and ticket prices, click on:

See our highlighted musical acts below:

Three Dog Night

Performers of such radio hits as “Never Been to Spain,” “An Old Fashioned Love Song,” “Mama Told Me Not to Come,” and “Joy to The World” (that’s the one about Jeremiah the Bullfrog.)

  • Show time: June 20th at 9:30 PM – Uline Warehouse Stage

Little River Band

These Australian rockers from Melbourne penned such hit singles as “Help Is on Its Way” and “Reminiscing,” which peaked at No. 3 on the Billboard Hot 100.

  • Show time: June 20th at 5:30 PM – Uline Warehouse Stage

Bob Bohm Comedy Magic Show

Wisconsin native Bob Bohm performs all over the country as a full-time magician. Perfect fun for the whole family – grandkids especially.

  • Show times: June 20th at 1:30 PM; June 21st at 12:45 PM – Northwestern Mutual Community Park

Modern English

Originating from Colchester, Essex, England, you may recognize Modern English from their international hit “I Melt with You”, a Billboard charter back in the 80s.

  • Show time: June 21st at 8:15 PM – UScellular Connection Stage


Formed in Columbus, Ohio by saxophonist Dan White, the Huntertones are known for their high-energy performances and horn-driven jazz fusion.

  • Show time: June 21st at 4:30 PM – Briggs & Stratton Big Backyard

Robin Pluer and the R&B Coquettes

If you attended Bastille Days in Cathedral Square last year, you may have caught sight of Robin Pluer on stage singing Edith Pilaf favorites.

This time around, Robin Pluer and the R&B Coquettes will be performing in perfect three-part harmonies, bringing their eclectic blend of Classic Soul, Rock ‘n’ Roll, French Chanson, Old Country, and original tunes. If you’re a local, you may have seen Pluer at Coffee Trader on Downer Ave back in the day.

  • Show time: June 27th at 5:30 PM & 7:30 PM – Johnsonville Summerville Stage

REO Speedwagon

If arena rock ballads are more your style, Illinois originals REO Speedwagon will be playing their number one hits “Can’t Fight This Feeling” and “Keep On Loving You.”

  • Show time: June 28th at 9:30 PM – BMO Pavilion

Amy Lowe and King Katz

Award-winning singer songwriter Amy Lowe performs both Children’s and Contemporary Adult music. Her music inspires all ages.

  • Show time: June 28th at 2:15 PM & 5:30 PM – Northwestern Mutual Community Park

Main Street Song and Dance Troupe

See these talented young performers of this non-profit show choir between the ages of 12 – 18 perform sing and dance.

  • Show time: June 29th at 2:15 PM & 4:45 PM – Northwestern Mutual Community Park

The Box Tops

You’re sure to recognize The Box Tops from The Letter USA Today’s #26 Song of All Time, Cashbox Magazine’s 1967 Record of The Year. Be sure to buy your tickets to hear “Gimme a ticket for an aeroplane,”

  • Show time: July 5th at 3:00 PM – Briggs & Stratton Big Backyard

The Baseball Project

It has been a year since this supergroup released their latest album, “Grand Salami Time!” to fans, but they are sure to fill seats with their repertoire of songs fueled by their shared love of baseball and baseball players.

That is right. This supergroup, which includes two members of alternative rock stars R.E.M., has dedicated its time to writing and performing songs about America’s favorite pastime: baseball.

  • Show time:  July 5th at 3:30 PM – Uline Warehouse Stage

Headley Grange – Led Zeppelin

Taking their name from Headley Grange, the former workhouse turned recording studio utilized by Led Zeppelin for more than a handful of their exclaimed albums, Led Zeppelin cover band Headley Grange are Milwaukee locals who recreate and celebrate the music of Robert Plant, Jimmy Page, John Paul Jones, and John Bonham.

  • Show time: July 6th at 2:45 PM – Miller Lite Oasis Stage

Amy Grant

Amy Grant’s Heart in Motion album became a best-seller, selling five million copies in the U.S. With hits like “Good for Me”, “That’s What Love Is For,” “Every Heartbeat,” and frequent radio requests and chart-topper “Baby Baby.”

  • Show time: July 6th at 9:30 PM – Uline Warehouse Stage


Hailing from Waukesha, Wisconsin the BoDeans have been touring America’s heartland and beyond since the early 80s. A staple at county fairs for decades, the BoDeans are best known for their easy-listening alt-rock hit “Closer to Free,”

  • Show time: July 6th at 9:30 PM – Generac Power Stage

With all of these performers and more, there is sure to be quite a crowd at and around the Summerfest grounds. Consider leaving your car at home and using alternative transportation to get there and avoid the traffic both in vehicles and on foot:

Outdoor Activities and Parks

If you’ve spent any time in Milwaukee, you may have noticed our abundance of green spaces. Our residents have over 150 parks to explore and enjoy. These include dog parks for your canine companions.

Golf courses for tee time. Plenty of opportunities to sun, swim, kayak, or surf on our beaches. We also have miles of trails to walk, hike, or bike right in our own backyard. Another unique feature of our Milwaukee Park system? We keep the tradition of the beer garden, and live polka music, alive here.

  • Veterans Park: One of our largest Milwaukee. The park hosts many outdoor events and is pet and family-friendly, including a Veteran’s Memorial, a 14-acre lagoon, walking trails, and a kite store with plenty of open green space to fly your new kite.
  • Riverwalk: Follow the Milwaukee River through downtown Milwaukee. While in the Historic Third Ward, take a stroll down the Milwaukee Riverwalk and snap a picture/take a selfie next to the Bronze Fonz.
  • Bradford Beach: Sun, sand, volleyball, and drinks.
  • Brewers games: Cheer on the Brew Crew at a baseball game.
  • Lakeshore State Park: Get away from it all in your own backyard. Linked to several other nearby parks and trails on the lakefront, Lakeshore State Park offers accessible paved trails, benches, and a variety of flora and fauna as you walk along the water.
  •  Milwaukee County Zoo: The grandkids will love seeing the penguins and learning about different species of animals and dinosaurs. If they are a little older, they are sure to want to take the zip line for a ride.
  • Golf, tennis, or pickleball: Plenty of courses and courts for athletes of all ages.
  • The Oak Leaf Trail: Looking for a longer walk, a hike, or a bike ride? The Oak Leaf Trail with its numerous branches connecting Milwaukee’s main parks, extends along the Milwaukee River Line, running from the north at Brown Deer Park down along the Milwaukee River through several of the main Milwaukee parks, past the Urban Ecology Center, and ending in Juneau Park & Lakeshore State Park area near the lakefront downtown.

Of course, there is plenty of green space right at Eastcastle Place. From our spacious interior courtyard and gardens to our gazebo courtyard on the corner of Bradford Ave and Downer Ave, residents can soak up the sun in their own backyard.


Senior couple enjoying a fair ride


The Wisconsin State Fair Is a Summer Spectacle You Can’t Miss

Held annually at the Wisconsin State Fair Park in the nearby suburb of West Allis, the Wisconsin State Fair is worth marking on your calendar. With a week and a half of events and attractions, the fair is well attended for good reason.

Popular attractions at the fair include rides, games, agricultural exhibits, places to grab a drink such as the Wisconsin Wine Garden, and a smorgasbord of fair food, most notably the Iconic Original Cream Puffs. It is no surprise attendance numbered over 1 million back in 2019.

If you’re feeling adventurous, or have thrill-seeking grandkids, the fair’s Spin City offers a variety of games and rides including the Sizzler, the Freak Out, the Stratosphere (a 200-foot-tall swing ride), and Comet 2, a forty-foot roller coaster.

Classic Fair Food for a Culinary Adventure

For many others, the Wisconsin State Fair begins and ends with THE FOOD. Each year, vendors surprise attendees with new and inventive takes on old favorites.

Yes, you’ll be able to buy the usual fair food like burgers, brats, pizza, pasta, tacos, popcorn, nachos, pretzels, and chicken wings, but you’ll also see these and other everyday foods reimagined by vendors. Attendees should look forward to many different food options, both traditional and new, and inventive takes on old favorites.

There will be a fair share of battering, deep-frying, and putting it on a stick. Fairgoers on the go can reach for options such as deep-fried mashed potatoes on a stick or a beer-battered brats on a stick for an easier way to walk and eat, but there will still be plenty of seating for sit-down dining.

Did someone say CHEESE CURDS?

Whether you like them served cool and “squeaky” or battered and deep-fried, cheese curds are a must-have snack at the Wisconsin State Fair. If you haven’t had your squeaky cheese curds or their deep-fried variety this year, you’ll have a great opportunity at the fair.

Celebrating a Century of Sweetness

The same can be said about the iconic Original Cream Puff. Head to The Original Cream Puff Pavilion where you will be able to enjoy a giant cream puff, sold single, in three-packs, and six-packs.

Watch as the cream puffs are baked and filled to burst through the row of windows in the pavilion. First sold at the State Fair in 1924, an average of 400,000 of these desserts are consumed yearly.

This year marks the 100th “Birthday” of the Cream Puff at the Wisconsin State Fair. This year also marks the 8th year the Wisconsin State Park Foundation is putting on the Annual Cream Puff 5k. Join the In-Person 5K Run/Walk or support the fundraiser virtually.

This year, the Wisconsin State Fair runs from August 1st to 11th.

Learn more at

Going to the fair? Follow this link to get there:

Unique Ways to Enjoy Milwaukee Summers

The city of Milwaukee has something for everyone to enjoy, and summer offers both unique indoor and outdoor activities. For every stadium or grandstand, there is a theater or club. For every bar, a café, for every food truck, a gourmet restaurant.

If you’re looking to get lost in a crowd and join the cheering or look forward to attending an evening with the author at Boswell Books on Downer Ave, Milwaukee, Eastcastle Place’s great location on the Eastside puts your next Milwaukee adventure at your doorstep.

Other activities and events include:

  • Petfest
  • Bastille Days
  • Church Festival
  • Milwaukee Night Market
  • Lavender Fest
  • Sculpture Milwaukee
  • Chill on the Hill
  • Brewery tours
  • The Milky Way Drive-In


For dates and locations of these and many other events, follow this link:

There are many ways to enjoy your retirement free time this summer, and year round. While the Milwaukee area has a plethora of events, activities, and local businesses to explore, what matters most in the end is that you are spending time doing the things that make you happy and with the people you love.

At Eastcastle Place, you will have access to the Eastside of Milwaukee, and the Greater Milwaukee area, with a comfortable elegant home waiting for you at the end of the day.

Small-Town Friendliness in the Heart of a City

Live your best life on the Eastside. Our residents enjoy the small-town feel of a friendly community in the quaint Downer Ave neighborhood while having access to the Greater Milwaukee area and big city life.

Our community offers events, activities, trips, opportunities to socialize, and fine dining, all under one roof. Step outside your front door and explore the Greater Milwaukee area, knowing you have a maintenance-free home waiting for you at the end of the day.

Whether you are out in the community, taking a day trip, or traveling to another country, living in our community provides peace of mind and abundant opportunities to design and live the retirement lifestyle you have always wanted.

To learn more or schedule a tour, visit or call 414-219-1398.