A Chicagoan’s Guide to Visiting Winona
Influencer and photographer Craig Hensel called Winona home for ten years and returned from the Windy City for a late-summer weekend in 2026, reconnecting with the outdoor adventures, good food, art, and community that make Winona special. Check out his Winona weekend itinerary below that is perfect for adventure and food-lovers alike!
A Big Small Town
After checking in to Hotel 44 North located along the river and with all-modern amenities, Craig made his way (across the parking lot) to The Old Tiger for happy hour and dinner. Winona’s latest upscale restaurant to open, The Old Tiger offers steak, seafood, a full bar with craft cocktails, and rentable breakfast, lunch, and dinner space. The Patio at The Old Tiger is shared with their breakfast concept, Cafe Zorya. Freshly-brewed coffee, teas, and pastries are available daily.
Hotel 44 North Lobby
Oysters at The Old Tiger
A River Runs Through It
Craig attended Bluffs2Backwaters while in Winona — one of Winona’s signature festivals that is all about the river, watercrafts, and love of the great outdoors. Hosted at Prairie Island Campground, the festival hosted Dam to Dam canoe and kayak races, hot dog cook outs, craft beer pop-ups, and campfire concerts.
Open through end of October, Prairie Island Campground offers rentable camp sites, watercraft rentals, community gardens, food truck pop-ups, bike rentals, and so much more all summer and early fall.
There are over 50 ways to paddle, float, and boat in Winona! Maggie Sather pictured at Prairie Island Campground.
Mike Munson at Campfire Concert Series
We’ve Got More Than A View
After a morning of paddling and an afternoon of sunning, we suggest cooling off at the Minnesota Marine Art Museum (MMAM). With six rotating exhibitions and Waterbar Cafe + Provisions, you can enjoy a carefully curated meal and museum tour.
MMAM is located on the banks of the Mississippi, a short drive from downtown Winona.
Dance The Night Away Downtown
Ready to roll back downtown? Across multiple dates in summer, the Dancing in the Streets events brings live music, dance lessons, and community to downtown Winona. Peruse 3rd Street for cute boutiques, local coffee shops and bars, and swingin’ in the streets. The best brick fire pizza is found at Muddled Thyme, every trinket imaginable is discovered at Heart’s Desire, and there are more plants than people at Green Thumb Artistry.
Line Dancing in the Streets in Downtown Winona
All Photos By: Craig Hensel / Instagram: @thecraighensel
We welcome travelers from all over the globe to our humble home. Each event, business, and city block is crafted with care. Whether you want to spend fall with us lazing all day looking out over the Mississippi or jump right in and explore the backwaters, Winona welcomes you to our awesome abode.