17 Fun & Best Things to Do in Winona, Minnesota

Planning to visit Winona? Here’s a list of the best things to do in Winona that guarantees a memorable vacation for you, your family, or your friends.

Winona is a charming old town in the Mississippi River Valley is located in southeastern Minnesota near the border with Wisconsin. The town offers you limitless opportunities to have fun whether you are alone or with your family and friends.

It may be a small town with just over 1,056 but there’s a ton of fun things to do in Winona, likely more than you can imagine. From its picturesque bluffs to its mighty rivers and beautiful and varied cultural places, Winona has that perfect blend of indoor and outdoor fun mixed with that old Midwestern charm.

Things to Do in Winona, Minnesota

It is a great place to visit in Minnesota. There are so many things that you can do while visiting Winona. Here we’ve picked the best things to do in Winona, Minnesota.

1.  Go Kayaking and Canoeing

With its many water bodies and sloughs, Winona offers many opportunities for kayaking and canoeing. You can explore Winona’s sloughs using canoes made locally in the town by a company called Wenonah Canoe.

One of the most serene routes to canoe is along the Prairie Island sloughs as you join the Mississippi River. This route allows you to interact with the prairie winds as you paddle past the islands to the Dakota winter homes.

You can also paddle up the river as you take in the breathtaking backwaters and views of the beautiful and thick green scenery along this giant river. You will also get a chance to see the towering bluffs that line the river’s edge on both sides in the background. And, there is a visitors’ center, at U.S. 61 and Huff Street, where you can buy maps of the area.

If you want a canoe or a kayak, you can rent one at Lake Lodge Recreation Center, located around the east end of Lake Winona. It usually opens at noon, and you can enjoy its services by getting yourself a $22 yearly pass or paying $11 for a daily pass.

Alternatively, you can check out Prairie Island Campground, which also has canoes, kayaks, and even paddleboards.

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2. Attend The Great River Shakespeare Festival

This festival was started by three theater directors back in 2002 when they realized that there was a need for a Shakespeare festival in Minnesota. Winona lobbied to get the hosting rights and duly got the opportunity to do so. Visitors come from all the states for this six-week-long festival that is hosted at Winona State University.

The festival calendar includes plays, concerts, lectures, art exhibits, and even walking tours for new visitors facilitated by the Winona County Historical Society.

You could also have a unique chance to participate in coffee house discussions with cast members and experts. There are plans to build a permanent theatre for the same. This year’s festival is slated to take place between mid-June and early August.

See Related: Best Things to do in Fergus Falls, Minnesota

3. Go Hiking and Camping at Sugar Loaf Bluff

If you love the outdoors, you cannot leave Winona without hiking Sugar Loaf bluff. Being one of the most iconic attractions in this town, it should be on your list of what to see in Winona. Sugar Loaf is 85 feet tall, and you can see it towering high above downtown Winona and the rest of the sprawling scenic bluff country.

You can access the summit via two trails at Sugar Loaf. One is on the south side, where you go through a steep climb to get to the top, while the other is via a path on the northern side that is more favorable. It will take you about an hour to get to the summit.

Both trails are challenging, but the views at the top will be worth the effort. From the top, you will be able to see the entire town of Winona spread out below you, etched between the Mississippi River and Lake Winona.

And you don’t need any specialized equipment or clothing – even with just your tennis shoes, you are good to go. But if you are visiting during the rainy season, getting some hiking boots with good tread is advisable, as it might get muddy in some places.

However, if you plan on climbing the rock itself, you are advised to use climbing equipment, and you also need to be a technical climber to hack it.

See Related: Best Family Vacations in Minnesota

4. Go for a bike tour of Winona and the Mississippi River Valley

Winona is very bike-friendly, and this is one of the cheapest things to do in Winona. With its low traffic and clean streets lined with trees, you could spend hours riding as you enjoy the beautiful architecture of the houses in the town.

If you’re in the mood for adventure, you could leave the comfort of the paved streets and head into the biking trails. There are several popular biking trails that you can explore besides the bike-friendly streets. One of the most popular trails is the Mississippi River trail.

Another popular route involves riding along Prairie Island Road. This road takes you away from heavy traffic and into quiet streets with scenic views of wetlands and backwaters. You can take a breather on Prairie Island, stop for a picnic, or just watch birds.

There is also a water fountain near the picnic shelter and another handy addition – a portable toilet. It is also possible to bike up the Sugar Loaf following the trails used by hikers, but this requires a lot of stamina.

See Related: Fun & Best Things to do in Minnesota

5. Take on winter sports

Winona Forest offers excellent skiing opportunities, especially in winter. There are more than 50 miles of groomed, track-set trails for skiing, skating, and striding. The trails are friendly to skiers of all ages and different levels of skill.

So whether you are a novice or a seasoned skier, you will enjoy your experience in Winona. Apart from the groomed trails, you will also see different species of trees and wildlife.

St. Mary’s University, located at the foot of the bluffs at Winona’s edge, is also famous for its world-class skiing facilities. It has well-laid tracks that lead up the valleys and into the wooded hillside. You will pay a small fee to access the trail.

You can also check out Frontenac State Park, another popular place for skiers. It has over 10 kilometers of ski trails that are neatly groomed. The Great River Bluffs State Park, located in the bluffs southeast of the town, is also ideal for skiing with its 15 kilometers of trails.

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6. Go camping or take a picnic

Winona has great picnic and camping facilities. For example, after a long day hike in the bluffs, you can settle down for a picnic at the picnic tables, usually provided for hikers and tourists.

You get to experience both hiking and a picnic at Garvin Heights Park. And in case you did not pack for a picnic, you can order from the nearby Winona Family Restaurant.

If you would like to spend a night outdoors, there are many camping facilities in Winona. The Prairie Island Campground, for example, is popular with campers. They offer both tent camping and tiny house cabins depending on what you want.

Other campsites include Winona Marina and Plar-mor Campground. In most of these places, you will be provided with so much more than just a campground. You can get a chance to participate in morning yoga classes, live music performances, and even themed weekend parties.

The camping rates in Winona vary depending on the campground you’ve settled on and how long you intend to stay. Most places charge between $20 and $40 a night. You can even get custom packages in some places depending on the activities you would like to engage in besides camping.

If you have an RV, you can also find RV parks at campsites in Winona, but they tend to charge more compared to a campground stay. Rent an RV with RVShare, it’s like the Airbnb of RV rentals.

See Related: Best State Parks in Minnesota

7.  Grab a bit to eat at one of Winona’s classic restaurants

Another great travel destination indicator is the dining experience, and Winona offers excellent opportunities for eating and drinking on Lake Street of historic downtown Winona. There is a locals’ favorite, called the Winona Family Restaurant, where you can experience delicious food featuring local Minnesota cuisine, from breakfast treats to comfort foods.

Another famous restaurant is Lakeview Drive-Inn. Founded in 1938, it’s undoubtedly the oldest restaurant in Winona. They serve their famous root beer, and visitors get to see the historic barrel that is carved into an elm tree stump using a chainsaw.

In case you are not sure of things to do in Winona at night, there are several restaurants and sports bars, open even during the late hours. The BoatHouse, for instance, is a riverfront restaurant that offers a perfect setting for an evening romantic dinner. Its menu comprises river-inspired dishes, and you can also opt for its cocktails as you watch the flow of the Mississippi.

Some venues also schedule evening concerts for the public. If this is something you would like to explore, you can check out Theatre du Mississippi at the Historical Centre located on Main Street. St. Mary’s University, located at the foot of the bluffs, also hosts concerts from time to time.

See Related: Things to do in Edina, Minnesota

8.  Visit the Minnesota Marine Art Museum

When it comes to culture and history, Winona is also not left behind. There are multiple cultural places in the town that focuses on preserving Winona’s heritage and history as well as featuring top-rated art from around the world.

First, and probably the most important of all, is the the Minnesota Marine Art Museum, one of the best museums in Minnesota and likely the most underrated of all art museums in the Midwest. Nestled along the banks of the Mississippi River, this nonprofit art museum offers enjoyable visual art experiences through education and exhibitions.

Among the numerous masterpieces displayed are works by Monet and Picasso, making it one of the most unique and significant collections of marine art in the Midwest.

Minnesota Marine Art Museum also provides guided tours and gallery experiences for individuals and families, making it an excellent activity to consider if you’re looking for an activity you could do with your family.

If you’re in town for a weekend, visit the Minnesota Marine Art Museum for their art education programs, offered every second Saturday of the month.

9. Lake Park

Winona is known for its stunning natural landscapes, and one of the best ways to experience it is at Lake Park. This primary city park surrounds the beautiful Lake Winona, offering guests a biking and walking path, playgrounds, boat fishing, bandshell, a beach, rose garden with gazebo and picnic sites.

Outdoor sports can rent equipment from the nearby Lake Lodge Recreation Center, such as kayaks and canoes for exploring the lake or bikes for cycling around the five-mile blacktop trail which encircles it.

10. Polish Cultural Institute and Museum

Another great museum to visit is the Polish Cultural Institute and Museum. It has exhibits on everything from immigration to language preservation, as well as an archive of Polish books and newspapers. Polish Cultural Institute and Museumhas scheduled festivals and activities all year round, so there will be something for you and your family to enjoy whenever you visit.

While there, remember to check out Schulz House, which showcases Polish art and decor from over one hundred years ago. Other notable exhibits at the Polish Cultural Institute and Museum are artifacts from the immigration history, artwork, and rare books.

11. Great River Bluffs State Park

Great River Bluffs State Park is a must-see for nature lovers and adventurers. Located in Winona, Minnesota, this state park offers visitors 6 miles of hiking trails, 9 miles of mostly intermediate biking trails and spectacular views of the Mississippi River.

With the oak-hickory, maple-basswood forests, pine plantations, and goat prairies, Lake Park is a great spot for bird watching, sightseeing and exploring the diversity of the area.

12. Pickwick Mill

Located in Winona, Minnesota, the Pickwick Mill is a great place to explore the area’s history. Built between 1856 and 1858 by Wilson Davis and Thomas Grant, the mill was originally designed as a sawmill, but was soon converted into a grist mill. The mill is powered by operating millstones from the 1400s, making it one of the oldest water-powered gristmills in the state.

Visitors to the Pickwick Mill can explore its six-story stone building made from local limestone and learn about Minnesota’s flour milling history.

13. Winona County Historical Society

The Winona County Historical Society has been around since 1857 and has an extensive collection that includes historic artifacts and documents from the area’s past, as well as an excellent rural heritage museum on display.

The archives are another highlight at Winona County Historical Society. They contain more than 100,000 pieces of material relating to Winona County from its earliest days through present times–and there’s more being added all the time.

If you’re interested in learning about how this region came into being (and why), check out what these archives have for you. You’ll find everything from photographs taken during early exploration expeditions through papers written by local entrepreneurs who helped shape our community into what it is today.

The Winona County Historical Society is a great thing to do in town with kids, as it also features interactive displays regarding Winona’s logging history and development.

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14. Spend a day at the beach at Michael LaCanne Park

Our list of things to do in Winona won’t be complete if we fail to mention the beautiful man-made beach at Michael LaCanne Park. This is a good place for children, especially if you visit Winona during the weekends. They can spend an entire day as they swim, play in the sand, and even try their hand at the fishing pier.

The park has a playground and a picnic pavilion, thus ideal for anyone looking to spend some time by the water. Other places that offer water activities include the Bob Welch Aquatic Center.

It has a large 208-foot water slide, an Olympic-size pool, a pool for kids, and bocce courts, among other entertainment facilities.

15. Watkins Heritage Museum and Store

The Watkins Heritage Museum and Store is a great place to visit in Winona, Minnesota. Located in Minnesota’s bluff country, it features scenic bluff top views of the majestic Mississippi River valley offering. It is also home to a variety of historical artifacts that trace the company’s 147 year long history.

Here visitors can view old products, advertising, photographs and more. The museum offers free admission so it’s a great way to learn about the history of Winona without spending a fortune. Plus, the attached store offers over 350 different Watkins products including Watkins Vanilla and other goodies for visitors to take home.

16. Levee Park

Levee Park in Winona Minnesota is a great place to visit for outdoor recreation. The park sits along the Mississippi River and boasts some of the best views of the river, as well as providing plenty of activities to keep you busy. There are trails suitable for walking, biking, or jogging, playgrounds for children, and several picnic areas. Visitors can also take part in canoeing, kayaking, and fishing in the park.

The park’s natural beauty makes it an ideal spot for bird watching with many species of birds making their home here throughout the year. For those looking for a more leisurely activity there are benches to sit on and enjoy the scenery

17. Tour the Winona County Courthouse

Winona County Courthouse is one of the most impressive county courthouses you may ever come across. Originally designed by Charles G. Maybury, it is dressed in a Richardson-Romanesque design that has been beautifully preserved over the decades.

In particular, the sandstone buffs, brown stone trims and the twin towers bring about an influence from the Victorian period – just take a closer look at the carvings to discover its mysteries.

Formally placed on the National Register of Historic Places for its unique local significance since 1970, Winona County Courthouse is certainly worth visiting for both locals and travelers alike.

What is Winona, Minnesota known for?

Winona is a beautiful and vibrant Minnesota city that offers plenty of activities and attractions for visitors. Winona is known for its riverfront as it’s one of the best in the state, with a long stretch of green space, beautiful parks, and plenty of places to walk or bike on the banks of the Mississippi River in southeast Minnesota. The town is also the home to Winona State University.

Beyond that, the city has several top attractions from the Minnesota Marine Art Museum to the Garvin Heights overlook, so there are plenty of opportunities to explore the beauty of this small city. Kayaking and canoeing on the Mississippi River is a popular activity, as well as visiting the Watkins Heritage Museum and Store for some unique souvenirs.

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