Racing through June 🚴

Inside: Shorewood Criterium, Strawberry Fest, Summerfest, Fun before the Fourth, Rock the Fox

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It's a big week on the calendar. Summerfest rolls into its second weekend, the Cedarburg Strawberry Festival takes over Cedarburg, and Tours of America’s Dairyland races through Shorewood, Rock the Fox returns and it’s already time for Family Fun before the Fourth.

If you find these useful, you can assist North Shore Family Adventures continuing to bring you these events with a premium membership of just $5/month. Thank you for your support!

Know the North Shore: Shorewood Criterium

The 22nd Annual Shorewood Criterium Classic returns Friday, June 26, bringing a full day of bike racing, food, drinks and family fun to the streets around Lake Bluff Elementary.

Part of the Tour of America’s Dairyland, the free event features races for juniors, amateurs and pros, plus kids races, the Dairyland Mile, bike decorating, face painting and free frozen custard from Culver’s after the kids races. New this year, families can enjoy a food court near the Lake Bluff baseball diamonds, along with drink stations from Draft & Vessel, Scout Wine Merchants and Three Lions Pub near the start/finish line.

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Summerfest Rolls Into Weekend Two

The Big Gig keeps going with its second weekend, Thursday through Saturday, June 25–27, before wrapping up over the July 2–4 weekend at Henry Maier Festival Park. If you haven't made it down yet, this is a great week to go — especially with kids. We pulled together guides on how to get into Summerfest for free, family-friendly shows at Summerfest, and how to get to Summerfest from the North Shore.

For the full summer festival calendar, bookmark our Milwaukee Summer Festivals 2026 guide.

Cedarburg Strawberry Festival

Cedarburg Strawberry Festival

The Cedarburg Strawberry Festival returns Saturday and Sunday, June 27–28, turning historic downtown Cedarburg into Wisconsin's sweetest weekend — and it's completely free. Expect strawberry shortcake by the thousands, more than 300 artists along Washington Avenue, and a dedicated kids' zone at Cedar Creek Park with a live mermaid, a petting zoo, bounce houses, and the CedarQuacker 500 duck races. It's about 25 minutes north of Milwaukee and entirely stroller-friendly. Read our full Cedarburg Strawberry Festival guide.

A few tips: parking is the hardest part, so use one of the free remote lots with a shuttle and arrive before 10:30 a.m. on Saturday, bring cash for the strawberry vendors, and note that pets aren't allowed. For families, Sunday morning is the sweet spot — start with the all-you-can-eat strawberry pancake breakfast at Cedar Creek Settlement, then explore before the afternoon crowds build. Here are 15 things to eat, drink, and do while you're there.

Family Fun Before the Fourth

Celebrate Independence Day early at Family Fun Before the Fourth on Saturday, June 27, at Thiensville Village Park. The parade steps off at 10:30 am, followed by free ice cream, all-day entertainment, Little League All-Star games, water ski shows, face painting, music, food vendors, and family fun throughout the park. Bring blankets and chairs, stay for dinner, and cap off the celebration with fireworks at dusk.

Rock the Fox Returns

Fox Point’s free concert series Rock the Fox is back for 2026, bringing live music, lawn chairs, dancing, and neighborhood fun to Longacre Pavilion. The 2026 schedule kicks off TODAY, Wednesday, June 24, with Boys & Toys. New for 2026, the Wisconsin Athletic Club will lead free fitness classes, including yoga and Zumba, from 5:45–6:30 p.m. before the concerts.

Summer Camps!

Keep your kids active and engaged. Sign up for classes at The Little Gym and make summer one to remember!

See you out there,
North Shore Family Adventures

P.S. Forward this to anyone still asking, “What should we do in June???”

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