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

Winona is a charming old town located in southeastern Minnesota near the border with Wisconsin. Winona 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, as of the 2010 census, but there’re a lot of things to do in Winona 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.

It is an unforgettable place to visit.

There are so many things that you can engage in while visiting Winona.

Here we’ve picked 9 of the best things to do in Winona, Minnesota.

Top Fun Things to do in Winona

1.   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 their services by getting yourself a $22 yearly pass or pay $11 for a daily pass.  

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

2.   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 years’ festival was slated to take place between June 21 and August 2 but was canceled.

3.   Hiking Sugar Loaf

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 the town.

You can access the summit via two trails. 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.

4.   Biking

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 to 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.

5.   Cross-Country Skiing

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 the 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.

6.   Picnic and Camping

Winona has a 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.

7.   Dining

Another great travel destination indicator is the dining experience, and Winona offers excellent opportunities for eating and drinking. There is a local restaurant, the locals’ favorite, called the Winona Family Restaurant. Here you can experience the local cuisine, from breakfast treats to comfort foods, and it’s a good stopover after a long day hiking or sight-seeing.

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 of river-inspired dishes, and you can also opt for their 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: 12 Top Things to do in Edina, Minnesota

8.   Visit Museums

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. This means that there’re plenty of things to see in Winona, as these museums showcase paintings and art exhibitions, as well as offer educational programs to the public.

Firstly, you can visit the Minnesota Marine Art Museum for their art education programs, offered every second Saturday of the month. The museum also provides guided tours and gallery experiences for individuals and family, making it an excellent activity to consider if you’re looking for an activity you could do with your family.

Another great museum to visit is the Polish Cultural Institute and Museum. This museum has 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 are artifacts from Polish history, artwork, and rare books.

In case you visit during fall, you can take part in the annual Apple Festival for music, crafts, and delicious food.

The Winona County Historical Society is also worth a visit, especially for children. They are allowed to touch the displays as they get lessons on Winona’s logging history and the many inventions of the area.

9.   Man-Made Beach

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 little children, and bocce courts, among other entertainment facilities.

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