TosaFest, a classic end-of-summer fest just west of Milwaukee, is coming up this weekend! On September 6-7, the annual staple in the charming suburb just 15 minutes from downtown has a little bit of everything to ensure you give summer a farewell toast. From a curd-crushing contest to Kidsfest, here’s how to get the most out of this Wauwatosa celebration.

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What to See and Do

While Wauwatosa is traditionally known for its outstanding boutique shopping and family-friendly atmosphere, there’s so much to do at TosaFest for every member of your crew. Here are just a few ideas:
 

Arté in the Street Painting Experience

Friday, September 6
5-7:30 p.m.

Try a different style of impressionism at Arté Wine and Painting Studio street painting experience. Unleash your inner artist and create a masterpiece worthy of hanging in any art gallery. Just choose one of Arté’s popular paintings, including Monet’s Bridge, then follow the instructions to bring the piece to life. Tickets are $40 and are available online here.


Curd Eating Contest

Saturday, September 7
Noon

Do you have what it takes to be Tosa’s Top Curd Crusher? Test your dairy-loving mettle against other contestants as you take down a pound of fresh, squeaky curds from The Village Cheese Shop. Or, if you’d prefer to take in the curd carnage from a safe distance, squeak on by for an afternoon of cheddar delight at the Underwood Experiences Tent. Just chew it!


Oktoberfest Stein-Holding Competition

Saturday, September 7
4:30 (Women’s) and 5 p.m. (Men’s)

Eins, zwei, g’suffa! A test of who can hold the most before the prost, the Oktoberfest Stein-Holding Competition in benefit of the Wauwatosa Historical Society is the ultimate feat of strength. Looking for a sign to try to hold the stein the longest? Look no further! Winners of the men’s and women’s stein-holding competitions get a Draft & Vessel gift certificate, and all participants earn a commemorative stein with discounted refills. Sign up today!


Pairings on the Park

Saturday, September 7
3:30 p.m.

Raise your glass of wine up for this dynamic cheese pairing lineup! Pairings on the Park features five wines expertly paired with five cheeses—including cheeses featured on “Top Chef: Wisconsin” earlier this spring—for a match made in Wauwatosa. Whether you’re a wine and cheese connoisseur or a beginner looking to learn more, after your informal pairing experience, you’ll walk away more knowledgeable about the tasty duo. Get your tickets here!
 

Live Music

With music all weekend long, drop in and enjoy the tunes of local bands at three stages throughout the TosaFest grounds. Check out headliners, including JOE 2.0, Landline, The Hungry Williams, and so much more great entertainment throughout the three-day celebration. See the full lineup here.

 

Shopping

The boutique shopping around Wauwatosa is sensational any time of year, but this weekend, you can shop the cute artisan and specialty shops alongside a wide selection of vendors showcasing their talents and wares amongst the festivities with Marketplace vendors all over the TosaFest grounds. Peep the participating vendors here.

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Bites to Eat and Chew

Would it really be a festival in Milwaukee without vendors selling food so good that you have to go back for seconds? Here’s a little sampler of the restaurants, food trucks and stalls serving a slice of Tosa fresh for you.

See the full list of restaurants, food trucks and vendors here.

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Spaces for a Drink or Two

We may have a few weeks until the official first day of fall, but with the kids back in school, the return of football and almost perfect weather for a day out on the town, there’s no better setting to enjoy a beverage or two during this pre-autumn preview.
 

Wherever you wander during TosaFest, an ice-cold brew is never far away from you. There are five beer gardens spread across the TosaFest map for Draft & Vessel’s Oktoberfest celebration, along with a SpritzGarden with The Village Cheese Shop and wine by The Ruby Tap. Grab a beverage of your choice as you explore, or kick back and enjoy your pour.

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Family Fun for the Whole Crew

Of course, TosaFest is a family-friendly atmosphere, with plenty of fun for everyone. Here’s just some of the family fun you can find throughout The Village of Wauwatosa this weekend.


Kidsfest

Saturday, September 7
11 a.m. – 8 p.m.

On Saturday, TosaFest is also Kidsfest, with nine hours of activities and fun for the whole family, including inflatable bounce houses and slides, games like cornhole and activities sure to ignite every kid’s excitement.
 

Tosa Bike Garage Balance Bike Village

Saturday, September 7
11 a.m. – 1 p.m.

Also on Saturday, at Hart Park across the street from TosaFest, the Tosa Bike Garage is hosting a gathering of balance bikes, with an agility course for kids ages 3-6, along with helmet fittings and family fun. Designed to help kids build confidence and hone their balance skills, the event will take place in a grassy field, creating a safe and fun environment for all. Load up your kid’s balance bike and helmet for an exciting afternoon of cycling. More here!
 

Want to experience more of Wauwatosa’s wonders? Plan your trip today, or make it a weekend-long getaway and extend your stay!