While there are hundreds of ways to entertain yourself in Winona, below is a shortlist of things a lot of people say they enjoy the most. Whether indoors or out, high-brow or high energy, you’re going to find things you love here.

1. Minnesota Marine Art Museum

Prepare to be blown away. Picasso, Van Gogh, Monet, Renoir, Matisse – name a master painter and chances are good they have original artwork hanging in the Minnesota Marine Art Museum. The hook behind the museum’s name? Every piece except for one in the 1,800-piece collection has water in it. Beyond that, the subjects are as diverse as the artists who painted them, from a moody O’Keefe to a brilliant Degas to a jaw-dropping original “Washington Crossing the Delaware” painting that came to Winona from the White House – visitors are completely shocked to find this incredible museum in Winona. Bonus: Bring a picnic and settle in on the museum’s river walk to watch barges and eagles pass by while prairie gardens sway nearby in the breeze.

2. The Great River Shakespeare Festival

If you are lucky enough to be in town between late June and early August, grab a seat at a performance by one of the finest Shakespearean theater companies in the country. With a national cast and an approach that aims to make Shakespeare fun for even non-theater lovers, The Great River Shakespeare Festival entertains more than 10,000 people annually who come from far and wide. Come to a show and you’ll see why.

3. Bloedow Bakery

Savour Magazine called it one of the 50 best doughnut shops in the country and WCCO fans have named it Minnesota’s best bakery more than a couple of times and there is a reason why. Secret recipes handed down for nearly 100 years create incredible goods that taste like equal parts of love, flour and magic. The maple long john is legendary – in fact, the whole bakery is. It’s no wonder that doughnut lovers started their OWN Facebook fan page for Bloedow’s and a line forms out the door nearly every day of the week.

4. Amazing Hike & Bike Trails

Being cradled by towering bluffs definitely has an upside. Our bluffs are crisscrossed by every kind of trail, from gentle slopes for the kiddos to teeth-gritting descents for adrenalin junkies. If road biking is your thing, roads leading into and around Winona are bike-friendly, unless you’re talking about Garvin Heights Road, that is. The steep climb is such a phenomenal test of ability that Greg LeMond used to train here and bike races have used it for their toughest competitors. For a leisurely peddle, East and West Lake Winona are rimmed with paved trails that anyone can ride.

5. All Things Sugar Loaf

That rock pinnacle sitting about 500 feet above the city is more than just a landmarked recognized for more than a century from miles away. It is also part of Winona’s storied past and today part of its very active present.

Chiseled away by original settlers for its distinctive limestone used in every manner of local building project (the variety is called, of course, Winona stone), Sugar Loaf Bluff was originally a smooth dome cap that many said resembled the cap worn by the area’s Dakota Indian Chief Wapasha. Once it had been quarried to its current shape, it more resembled a lump of sugar our ancestors called a sugar loaf. There you go.

But today the landmark is teeming with life and is a core part of Winona’s recreation jam. Professional climbers have installed routes with varying degrees of difficulty all over the rock pinnacle, and a new hiking trail to its base offers sweeping views of the Mississippi River Valley.

6. History, History, History

From a sandbar in the Mississippi River to a bustling river port where more than 1,000 steamboats were docking each year by the turn of the century, Winona is steeped in the kind of history that left this town beautiful and keeps the stories fun.

Our extremely lovely Winona County History Center has our story on display in all its glory, and the Bunnell House, Watkins Museum, and Minnesota Polish Museum add to the richness of the tale with their own unique twists. And walking down the street is one of the best ways to see the past’s glamor, wealth and artistry still on display in our magnificently Victorian downtown. Grab a map from the History Center and take a self-guided walking tour through our streets to learn more about some of Winona’s stunning architecture.

winona, minneosta, entertainment, boats, bluegrass, festival7. Music and More Music

The Minnesota Beethoven Festival, the Boats and Bluegrass Festival, the Mid West Music Festival, the Highway 61 Concert Series and the Page Theater musical performances – not to mention massive downtown concerts and street dances plus an abundance of venues that feature everything from mellow coffeehouse music to punk bands – Winona is killing it in the music scene. Kiiiiiiiling it. Our event calendar is rich with music events big and small

8. Other Cherished Festivals & Gatherings

Our Shakespeare and Beethoven festivals are national-caliber events that bring actors and performers from around the globe, but that’s not all we’ve got going on in the entertainment realm. We warm up winter nights with the Frozen River Film Festival, celebrate in the summer with Steamboat Days, honor this land’s heritage with the Great Dakota Gathering, tap our toes with a Dixieland Festival and soak in the beauty of movement with the Driftless Dance Festival. Collectible car shows, Polish celebrations, history events, here in Winona, we know how to entertain ourselves and we’re good at it.

9. Lake Park

Fun fact: East and West Lake Winona used to be the main channel of the Mississippi River. We aren’t kidding – we were pretty much an island at one point. The river changed its route, ultimately closing off the inlet and outlet to that stretch, and Winona was blessed with two gorgeous lakes right in the city.

And we would never let such a blessing go to waste, having enshrined the entire area around them as a huge park. A paved trail circles both lakes and playgrounds and pavilions dot them from one end to the other. On East Lake, Lake Park Lodge sells annual and day passes, which entitle the bearer to free access to anything in the lodge. Standup paddleboards, canoes and kayaks, log rolling (ahem – let us know if you’re going to do it because we want to watch), plus lawn games, hammocks and more – it’s all there waiting to make your Lake Park visit extra perfect.

10. The Mississippi River, of course

As it passes by Winona, the river meanders through a labyrinth of backwaters and islands, creating gentle waters for a leisurely paddle on one of the world’s mightiest waterways. Don’t have a boat to paddle? No worries – you can rent one down at Prairie Island Campground. On the river, watch shy turtles dip into the water while eagles soar overhead looking for lunch. Fish, relax, play in the sand – nothing cleanses the soul like a day on the river.

And here is what makes Winona’s stretch of rive extra special: A wonderful man named John Latch bought up every inch of it that he could a hundred or so years ago and he donated it to Winona plus some state and federal conservation programs. That means when you paddle our backwaters, you can pull up on any island more or less to sit for a spell because it’s all public land.  Imagine that.

11. Our Local Restaurants

Here’s why this is special: Aside from some requisite highway fast food, Winona’s restaurants are all of the homegrown variety and we love that. Bottom line is that you aren’t going to find exactly the same dishes done the same way anywhere else, and that makes Winona delightfully unique. But don’t confuse “homegrown” with unrefined – you’ll find that our palette is interesting, complex and sometimes downright sexy when you start touring our local eateries. Juicy burgers with fries? Sure, we have that. Handmade pizza so good it might make you weep? Yup, we have that too. But you can also find things such as Prince Edward Island steamed mussels in curried coconut, cedar-plank salmon, grass-fed ribeye and wine lists that will knock your socks off.  Get your taste buds ready – it’s going to be fun.

12. Arts on SteroidsHBC-Fence-Mural-Public-Art-Winona-Minnesota

Maybe it’s something in the water or maybe it’s just because artsy people love beautiful places, but whatever the reason, Winona is brimming with extraordinary artists and a deep public sentiment that the arts are fun. What does that mean? Our two universities, local theater company, and event company Hurry Back Productions fill a deep roster year-round of theater, dance and music, often featuring national and international talent. In addition, pop-up art fairs, colorful murals beautifying our spaces, gorgeous gallery finds and events that are just a little bit more fun than the way other communities do them. Street dance? How about with mass swing dance lessons first and the region’s favorite 12-piece swing band? A concert? Let’s float the musicians out into the lake on a raft and loan out boats for the audience. We do things differently here and it might seem a little bit odd to some, but it’s very Winona and we love it. Come feel the fun vibe for yourself.

Check out these fun videos that offer a glimpse of Winona’s favorite things.