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Winona, Minnesota: Where Fun and Adventure Collide – Our Top Picks for the Best Things to Do and Places to Visit!

The festival calendar in this city runs across almost the whole year. Frozen River Film Festival takes February, the Art Walk takes May, Steamboat Days takes June, the Great River Shakespeare Festival takes July and August, and Boats and Bluegrass takes September. The scenic drives work in any of those months without exception. Fall is the one people plan around, because the bluffs turn and the Great River Road turns with them. Pick a month. Winona will already have something running that weekend.

Welcome to Winona, Minnesota, a small city set in the bluffs of the Mississippi River. With a population of just over 27,000, this town runs well above its weight for fun and adventure. A local after something new or a visitor working through the area, Winona takes you either way.

Artistic Winona is the reason to come for anybody who follows the arts. The Minnesota Marine Art Museum holds a serious collection of artwork inspired by water, while the Great River Shakespeare Festival brings the works of the Bard to life outdoors. If you want something more hands-on, check out the many art classes and workshops running across the city.

Outdoor Adventures are plentiful in Winona, with miles of hiking and biking trails, river views and chances to kayak and canoe. Historical Highlights include the Winona County Historical Society, the Watkins Heritage Museum and the Garvin Heights Overlook, which gives you the city and the Mississippi River from above. And do not forget the Food and Drink scene, which runs everything from farm-to-table cuisine to craft beer and cocktails.

Key Takeaways

• Winona, Minnesota offers a variety of activities for all ages and interests.
• Artistic Winona features the Minnesota Marine Art Museum and the Great River Shakespeare Festival.
• Outdoor Adventures, Historical Highlights, and Food and Drink are just a few of the many things to explore in this charming city.

Artistic Winona

Winona is a hub of creativity and artistic expression. From museums to galleries, there are plenty of places to work through and appreciate art in this city. Here are the two places to make time for if you follow art:

Minnesota Marine Art Museum

If art and the sea are your thing, the Minnesota Marine Art Museum will hold you. This museum houses a serious collection of marine art, including works by famous artists such as Winslow Homer and Claude Monet. The museum sits on the bank of the Mississippi River, which means the scenery does its own work while you look at the paintings.

Polish Cultural Institute and Museum

The Polish Cultural Institute and Museum is the stop for anyone interested in Polish art and culture. The museum runs exhibits covering the history and traditions of Poland, including folk art, traditional dress and religious artifacts. You also find contemporary Polish art on display, which gives you the country’s modern artistic scene alongside the older material.

A lifelong art enthusiast or somebody simply after something different to do in Winona, these museums hold up. So grab a friend, put on your most stylish beret, and go and work through the artistic side of this city.

Outdoor Adventures

You are in Winona, Minnesota, and you want some outdoor fun. You are in luck, because there are plenty of options to choose from. A leisurely picnic or a hike with some effort in it, Winona has you covered.

One of the places to start is the Mississippi River. This river runs right through Winona, and there are plenty of ways to use it. You can take a canoe or kayak out on the water, or you can sit back and take the view from one of the many scenic overlooks.

If you are more of a landlubber, do not worry. Winona has plenty of parks and hiking trails to work through. Great River Bluffs State Park, just across the river in Wisconsin, looks out over the Mississippi River Valley. Closer in, Lake Winona and Sugar Loaf Bluff are both strong options for a day hike.

For a more relaxed outdoor experience, head to Lake Park or Memorial Park. Both parks run picnic areas, playgrounds and plenty of green space to stretch out in.

If you want a rougher outdoor adventure, check out Prairie Island Campground or John A. Latsch State Park. Both run camping and hiking, and Mount Trempealeau in nearby Wisconsin is a strong spot for serious walking.

And do not forget the Frisbee golf course at Garvin Heights Park. It is a good way to spend a summer afternoon with friends.

Whatever time of year it is, Winona has something running. The fall colors, the winter snow or the summer sun, there is always an outdoor adventure waiting. So get out there and use it.

Historical Highlights

You cannot visit Winona, Minnesota, without working through its history. From the town’s founding in 1851 to its current standing as a working community, Winona has a great deal to tell you. Here are the historical highlights you do not want to miss:

Winona County Historical Society

If you are a history buff, you will want to visit the Winona County Historical Society. This organization is dedicated to preserving and sharing the history of Winona County, and it runs a museum, archives and a research library open to the public. You can learn about everything from the area’s prehistoric past to its more recent history.

Historic Sites

Winona holds many historic sites worth visiting. You can check out the National Register of Historic Places, which includes more than 30 buildings and sites in Winona. The highlights include the Winona County Courthouse, the Polish Cultural Institute and Museum, and the Historic Bunnell House.

Rural Heritage Museum

If the history of rural America interests you, the Rural Heritage Museum will hold you. This museum sits in the heart of bluff country, and it runs exhibits covering everything from farming to transportation. You see antique tractors, wagons and other equipment, alongside displays on rural life and culture.

A history buff or somebody simply after a good day out, Winona has plenty of historical highlights to work through. So grab your camera and get ready to step back in time.

Food and Drink

Winona runs a varied food and drink scene that will handle whatever you are craving. From local legends to family-friendly restaurants, the range covers everybody.

If you want a night out, head to Downtown Winona. This area is filled with bars and pubs where you can get a cold brew or a proper cocktail. Island City Brewing Company is a popular spot for beer, while Garvin Heights Vineyard runs a strong selection of wines with the Mississippi River in view.

For a classic American meal, check out Lakeview Drive-Inn. This family-owned restaurant has been serving burgers, fries and shakes since 1938. Winona Family Restaurant is the other option for a hearty breakfast or lunch.

If you want live music while you eat, head to Acoustic Cafe. This small spot runs a good room and food that holds up. Their menu covers vegetarian and gluten-free options, alongside a range of sandwiches, salads and soups.

For a dining experience you will not get elsewhere, try Blacktop Trail. This restaurant sits inside the Bud King Ice Arena and runs a menu of classic American dishes with a twist. You can eat while watching a hockey game or skating on the rink.

If you want waterfront dining, head to the Boathouse or Port 507. Both of these restaurants look out over the Mississippi River and run a menu of seafood and other classic dishes.

And no visit to Winona is complete without trying some Mississippi Sippin’. This local specialty is a mix of lemonade and vodka and turns up at many bars and restaurants in the area.

So a casual meal or a proper night out, Winona has plenty of options to handle your appetite.

Festivals and Events

Winona is known for its festival scene, and there is always something happening in this city. Here are the festivals and events to check out:

Great River Shakespeare Festival

If you follow the Bard, do not miss this annual festival. Held in July and August, the Great River Shakespeare Festival runs professional productions of Shakespeare’s plays alongside other classic works. A seasoned Shakespearean or a newcomer to iambic pentameter, you will get on with this festival.

Frozen River Film Festival

Held in February, the Frozen River Film Festival is a celebration of documentary filmmaking. The festival runs screenings of documentaries from around the world, alongside workshops, panel discussions and other events. If nonfiction cinema is your thing, do not miss it.

Winona Steamboat Days

This annual festival, held in June, is a celebration of Winona’s riverboat heritage. The festival runs live music, food vendors, a carnival and other activities. And do not miss the parade, which is one of the highlights of the whole thing.

Boats and Bluegrass Festival

This festival, held in September, is a celebration of bluegrass. The festival runs live music from some of the strongest bluegrass bands in the country, alongside workshops, jam sessions and other events. If bluegrass is your music, do not miss it.

Winona Art Walk

Held in May, the Winona Art Walk is a celebration of the city’s arts scene. The event runs open houses at local art studios and galleries, alongside live music, food vendors and other activities. An art lover or somebody simply after a good day out, the Art Walk is a strong choice.

Whatever time of year you visit Winona, you will find a festival or event that suits. From Shakespeare to bluegrass to documentary film, this city covers a genuine range. So pack your bags and get ready for it.

The North Shore Scenic Drive runs 145 miles from Duluth to Two Harbors. The Root River Trail runs 60. The Great River Road follows the Mississippi the whole way from Lake Itasca down to the Gulf of Mexico, which puts Winona somewhere near the top of it. Sugar Loaf is 85 feet of sandstone. Garvin Heights is a winding road with the whole city waiting at the end of it. None of that is a detour, because in Winona the driving is the thing itself.

Unique Architecture

You do not have to be an architect to appreciate the architecture in Winona, Minnesota. From the well-known Sugar Loaf to the historic Alexander Mansion Bed and Breakfast, the city is full of buildings worth stopping in front of.

One of the recognizable landmarks in Winona is the Sugar Loaf. This towering rock formation stands 85 feet tall and is made entirely of sandstone. It is a natural formation that has been holding visitors for years. You can hike to the top for the view over the city, but be warned, because it is not for the faint of heart.

If you want something more man-made, the Alexander Mansion Bed and Breakfast is the stop. This restored Victorian mansion is a real piece of Winona’s architecture scene. The intricate details and ornate design hold up to close inspection. And you can stay overnight and live in a bygone era for a night.

But the architecture in Winona is not limited to these two landmarks. The city is full of historic buildings worth checking out. Take a stroll through the downtown area and you see everything from art deco designs to Gothic Revival structures.

One building that stands out is the Winona National Bank. This well-known building carries a distinctive onion dome and is listed on the National Register of Historic Places. It shows what the city’s commitment to preserving its architectural heritage actually looks like.

So if you have a love for architecture, Winona, Minnesota is the place to be. From natural formations to man-made work of real quality, the city has all of it. So pack your bags, grab your camera and get ready for it.

Local Accommodations

So you are planning a trip to Winona, Minnesota, and you need somewhere to sleep? Winona has a range of accommodations to fit any budget and preference.

First up, we have hotels. Winona has a few chain hotels, including a Holiday Inn Express and a Days Inn. But why settle for a boring chain hotel when you can stay in a unique, locally owned hotel? Check out the Alexander Mansion Bed & Breakfast or the Carriage House Bed & Breakfast for a cozy and charming stay.

If you want a more urban experience, you might consider staying in Minneapolis and taking a day trip to Winona. Minneapolis has a broad spread of accommodations, from budget hostels through to high-end hotels. And you get access to all the attractions and nightlife Minneapolis runs.

If you are traveling with a larger group or staying longer, consider a vacation rental. Check sites such as Airbnb or VRBO for a range of options, from small apartments through to sprawling estates.

And finally, if you are in town for medical reasons or visiting the Mayo Clinic in nearby Rochester, consider staying in Rochester. There are plenty of accommodations to choose from, including hotels, vacation rentals and extended-stay options.

Wherever you stay, book early, particularly if you are visiting during peak tourist season. And do not forget to pack your sense of adventure.

Education and Learning

Who said learning cannot be fun? Winona runs a range of educational and engaging activities that will make you forget you are learning anything at all.

First up, Winona State University. If you want to further your education or simply walk the campus, WSU is the place to be. Take a campus tour and learn about the history of the university, or attend a lecture or event to widen what you know about a subject. You might even decide to enroll in something.

For a more historical angle, head over to the Winona County History Center. This museum is dedicated to preserving and sharing the history of Winona County. From exhibits on the Native American tribes that once lived in the area to displays on the early settlers and their way of life, there is a great deal to take in. The museum also hosts events through the year, including lectures, workshops and a haunted history tour during Halloween season.

But there is more. Winona also runs other educational opportunities, such as art classes at the Minnesota Marine Art Museum or cooking classes at the local culinary school. So widen your horizons and learn something new while you are in town. You might even turn up a new passion or a talent you did not know you had.

Scenic Drives

You are in for a treat if you like long views and open scenery. Southeastern Minnesota, and Winona in particular, holds some of the finer drives in the state. So buckle up, roll down your windows, and let us work through the scenic drives in the area.

First on the list is the North Shore Scenic Drive. Although not technically in Winona, this drive is worth making if you are in the area. The drive takes you along the rugged shoreline of Lake Superior and gives you the lake, the forests, the hillsides, the streams and the waterfalls. It is a 145-mile drive from Duluth to Two Harbors, and you will want to take your time over it. And stop at Split Rock Lighthouse, one of the most photographed lighthouses in the country.

Next, the Garvin Heights Scenic Overlook in Winona. This drive takes you up a winding road to the top of a hill, where you find a panoramic view of the city and the Mississippi River. It is where to watch the sunset or take the photographs you will actually keep. And if you are feeling adventurous, you can hike the trails around the overlook.

The other drive to make is the Great River Road National Scenic Byway. This drive follows the Mississippi River from Lake Itasca to the Gulf of Mexico, and the Minnesota portion of it is the part people talk about. You pass through small river towns, see historic landmarks, and get the river and the bluffs the whole way.

Last but not least, the Root River State Trail. This 60-mile drive takes you through the Root River Valley in southeastern Minnesota. You see forests, prairies, farms and small towns. And if you are feeling active, you can bike or hike the trail instead.

So there you have it, the scenic drives in Winona and southeastern Minnesota. Get ready for what the area actually looks like.

Family Fun

Looking for family-friendly activities in Winona, Minnesota? The small town character and the attractions here are the answer. Cooling off at the Bob Welch Aquatic Center or working through the Pickwick Mill gristmill, the city covers both.

If you want to beat the heat and make a splash, the Bob Welch Aquatic Center is the spot for family fun. With water slides, lazy rivers and kiddie pools, you can keep cool and occupied all day. And with affordable admission prices, a day at the water park will not break the bank.

For a more educational experience, head over to the Pickwick Mill gristmill. This historic mill runs tours and demonstrations showing how flour was made in the 19th century. It is a good way to learn about the history of the area while the family enjoys itself.

Looking for more things to do in Winona, MN? Check out the broad spread of family-friendly attractions in the city. From museums to parks, the range covers everybody. A day of adventure or simply time to slow down and take the small town character, Winona has all of it.

Frequently Asked Questions

What’s the best way to spend a weekend in Winona, MN?

You can start the weekend by working through the Great River Bluffs State Park. It is a good place to hike, bike and picnic. If you are feeling adventurous, you can camp there. And if you want some culture, check out the Minnesota Marine Art Museum, which holds artwork worth the trip on its own. And grab some grub at one of Winona’s many good restaurants.

Where can I find the most unique shopping experiences in Winona?

If you want shopping you will not get elsewhere, you are in luck. Winona runs a strong selection of local shops and boutiques. Check out the Blue Heron Trading Company for gifts and home decor. If you follow books, head over to the Book Shelf. And if you want new threads, check out the Green Closet. You will find something you want.

What are the top-rated restaurants in Winona, MN?

Winona has some genuinely strong restaurants, so narrowing it down is hard. But if we had to choose, we would point you at the Boat House for seafood, the Acoustic Cafe for coffee and live music, and the Blooming Grounds for brunch. And if you want pizza, check out the Jefferson Pub and Grill.

What quirky events can I attend in Winona, Minnesota?

Winona is known for its offbeat events, so you are in for a treat. Check out the Frozen River Film Festival for the documentaries. And if you follow music, do not miss the Mid West Music Fest. And if you are feeling brave, check out the Tews Corn Maze for some spooky fun. And do not forget the Great River Shakespeare Festival, where the performances are the reason people come back.

Frequently asked questions about Winona, Minnesota

Which Winona museum is worth building a whole morning around?

The Minnesota Marine Art Museum, which holds a collection of marine art including works by Winslow Homer and Claude Monet and sits directly on the bank of the Mississippi. Art classes run. The Polish Cultural Institute and Museum covers folk art, traditional dress and religious artifacts alongside contemporary Polish work. The Winona County History Center is the third one to consider.

Which Winona park suits a proper hike rather than a picnic?

Great River Bluffs State Park, just across the river in Wisconsin, which looks out over the whole Mississippi River Valley. Sugar Loaf Bluff is the climb inside town and it is not for the faint of heart. Prairie Island Campground runs camping alongside the walking. Lake Park and Memorial Park are the picnic answer.

Which Winona festival should you time the drive around?

The Great River Shakespeare Festival in July and August, which runs professional productions of Shakespeare and other classic works. Steamboat Days lands in June with live music, food vendors, a carnival and a parade. Boats and Bluegrass takes September and the Frozen River Film Festival takes February, which covers both ends of the year. The Art Walk is in May.

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