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Downtown Winona: Get Ready for the Sweetest, Craziest, Busiest Weekend of 2021

Wow what a summer we’ve had to this point in downtown! So many great events so far – Dine Out Downtown, Parade of Trucks, Steamboat Days, Swinging in the Street. It’s great to see so many awesome things happening again and bringing people to our beautiful, historic downtown!

We aren’t done yet though – this weekend might be the sweetest, craziest, and busiest yet. There’s Sweet Stroll on Thursday during normal business hours where you can shop at participating locations for some sweet deals and even sweeter treats. Friday and Saturday is Crazy Days, where you can “shop ‘til you drop” finding even more awesome deals at your favorite downtown shops.

But wait…. there’s more!!

Friday is also Dine Out Downtown on 3rd Street from 4-10 p.m. Island City Brewing Company is throwing a huge block party from 2:30-10 p.m. on Friday in partnership with Treedome and Boats & Bluegrass. Live music, great drinks, and fantastic fun awaits! Tickets are $25 and you can purchase them here. If live music isn’t quite your thing, you can also catch a Great River Shakespeare Festival show either Friday or Saturday. You can purchase tickets and learn more about the shows here.

Saturday is Steamboat Day’s “Show Your Ride” car show downtown on 3rd Street all day, and the first American Queen boat will be visiting from 7 a.m-6 p.m.

Long story short – if there was a weekend to spend time downtown it is definitely this one!

August is a bit more of a down month for the Main Street Program, but we are still plugging away at finalizing plans for Big Muddy Brew ‘N Que on September 4th and 5th! We are super excited to bring back our biggest event of the year after a hiatus in 2020. We’re going to have all the same fun activities we’ve had at the Que in years past – the Celebrity Rib Eating Contest is back again, along with the Bean Bag Tournament, Wine & Beer Tasting, Best in Area Grilling Competition, kid activities, and a bunch of great live music.

We also have something brand new this year in Axe Throwing (sponsored by Farmers Insurance Dave Jensen Agency). We’re super excited to have this popular activity at the Que. If you want to learn more about what else we have going on at this year’s event visit


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