13 FUN Things To Do In Winona, Minnesota

Winona is an undiscovered treasure in the Midwest, known for its stunning river valley landscapes and charming small-town vibe. 

This travel guide to Winona, Minnesota explores some of the top attractions and activities that make Winona an attractive destination.

 So, whether you’re planning a weekend trip or just curious about what Winona has to offer, keep reading to discover the best things to do in Winona, Minnesota and all this charming Midwest town has to offer. 

About Winona, Minnesota

view of Winona Minnesota with a statue in the foreground
Winona, Minnesota is a cute small, lakeside town. | Photo by Tom Fisk from Pexels

Located in southeastern Minnesota along the banks of the Mississippi River and just across the river border from Wisconsin, Winona is a small town with just over 25,000 residents. About a 2 hour drive from Minneapolis-St. Paul, you can easily get to Winona from Minnesota’s largest city, as well as La Crosse or Rochester.

Founded in 1851, Winona was once a booming lumber and milling town. The town’s historic Main Street district is known for its well-preserved, early 20th century buildings housing unique shops and businesses. 

Winona is a great place for outdoor enthusiasts to spend a day exploring the picturesque hiking and cycling trails and taking in the views of the Mississippi River Valley.

Whether you’re looking for a low-key vacation in a small town or just passing through on your way from Minneapolis to Milwaukee and want to take the scenic route, Winona will win you over with its small-town Midwestern charm.


The best things to do in Winona, Minnesota

While we live in California, we have family who live in Winona and visit during the summers. We immediately fell in love with this scenic town. If you’re planning a Midwest road trip to visit some of the incredible national parks in this part of the United States, and find yourself in Winona, here are 13 fun things to do in Winona, MN.

1. Hike Up To Sugar Loaf Bluff For Panoramic Views 

a hiking trail up Sugar Loaf Bluff in Winona MN
Taking a hike up Sugar Loaf Bluff is one of the best things to do in Winona, MN. | Photo by Adam Bouse from Unsplash

Sugar Loaf Bluff in Winona is a must-visit landmark, named for its resemblance to a cone-shaped sugarloaf. This impressive rock formation stands 500 feet above Lake Winona, with its peak rising an additional 85 feet. It’s not only a great hiking spot but also offers a section for rock climbers. Dogs with a leash are welcome here, as well.

Head to Sugar Loaf Bluff for its stunning panoramic views of the lake and town. Make sure to wear sturdy shoes and keep an eye on trail markers. Don’t miss capturing the breathtaking scenery from the top, so bring your camera along!

the view from the top of Sugar Loaf Bluff, one of the best things to do in Winona MN
The view from the top of Sugar Loaf Bluff. | Photo by Shreeyeh Rajan

2. Look at Marine-Themed Art at Minnesota Marine Art Museum

If you enjoy unique art, head to the Minnesota Marine Art Museum. This museum showcases a mix of classic and contemporary paintings and sculptures inspired by the water. Plus it has a beautiful garden. 

The museum has a 7-acre campus that’s located right on the banks of the Mississippi River. It has 6 galleries, educational spaces, and a retail shop. But the museum isn’t just for showing off marine art. It’s to help us understand how we connect with water and to think about marine art in new and different ways.

The museum is open from 10 am to 5 pm, except on Mondays and holidays. Admission is free for members, $10 for general admission, $8 for seniors, $5 for students, and free for kids 5 and under. Plus, students get in free on Thursdays!

3. Spend Time in the Outdoors On Lake Winona

lae winona in summer time
Lake Winona is great for outdoor recreation such as hiking, walking or water activities. | Photo by Amy Torbenson from Unsplash

If you love the outdoors, go to Lake Winona for its scenic hiking and walking trails. Enjoy the lake views and keep your eye out for the Sugar Loaf Bluff peeking out of the mountain.

If you’re up for some water activities, head over to the Lake Lodge Recreation Center where you can rent bikes, kayaks, canoes, or stand-up paddleboards during the warmer summer months. 

For those planning a family outing or a party, the Lions Shelter Gepner Pavilion is ideal. It’s a lakeside pavilion with multiple picnic tables set in a park-like setting near a playground. 

For the kids, there’s a huge playground named Every Child’s Dream Playground. It’s accessible-friendly, with plenty of parking and bathrooms. My niece loves this park and can spend hours here! 

4. Discover Winona’s Kashubian Roots at the Kashubian Cultural Institute & Polish Museum

Step into the heart of Winona’s cultural tapestry at the Kashubian Cultural Institute & Polish Museum. This unique museum celebrates the rich Polish and Kashubian heritage that has shaped Winona, known as the Kashubian Capital of America. 

With a significant number of Kashubian immigrants settling here in the late 1800s, their descendants continue to preserve and honor their unique culture. The museum offers an interesting look into this community, showcasing exhibits on Polish cultural heritage and the history of immigration from Poland.

If you’re interested in cultural history and genealogy, this museum is filled with stories and artifacts. Admission is free and it’s open Monday to Saturday from 10 AM to 4 PM. 

Don’t miss the gift shop for unique souvenirs. If you’re curious about Winona’s diverse roots, this museum offers a compelling reason to explore the lesser-known chapters of American immigration history. Keep an eye out for special exhibits and events that bring this rich heritage to life!

5. Enjoy Aerial Views of Winona at Garvin Heights City Park

the view from Garvin Heights City Park
Garvin Heights City Park also offers panoramic views of Winona. | Photo by Adrian Korpal from Unsplash

Garvin Heights City Park is a hidden gem in Winona, offering some of the most breathtaking views of the entire town. Surrounded by forested grassland, this bluffside park can be accessed by trail or road. 

From different vantage points, you get an expansive view of the Mississippi River and Winona’s picturesque setting along its banks. 

It’s amazing to see the whole town of Winona right before your eyes, and it isn’t hard to get there. Just a short drive and a very short walk from your car, and you’re there. When we visited, we were trying to spot familiar attractions from this view. 

Make sure to visit during autumn. The fall colors are stunning and transform the view into a vibrant tapestry of reds, oranges, and yellows.

6. Go Back in Time at the Winona County Historical Society

downtown Winona main street district
The Historic Main Street District in Winona is cute and worth exploring. It is also home to the Winona County History Center. | Photo by Amy Torbenson from Unsplash

The Winona County Historical Society is a charming little museum that’s filled with neat Winona artifacts and takes less than an hour to explore. They also offer historical tours, which are a great way to dive deeper into the local history. 

The Winona County History Center is the main attraction, featuring engaging exhibits and an art gallery that showcases regional artists. For those interested in research, the Laird Lucas Library & Archives are available by appointment. 

And don’t forget to check out the Museum Shop for some local souvenirs. Admission is $5 for adults and $3 for students, and it’s free for museum members, kids under 7, and students doing research. The museum is open daily, except on holidays.

Another part of the Historical Society is the Bunnell House, open from June to August, where you can step back into the 1850s. 

Also, don’t miss the Rural Heritage Museum, open during the Winona County Fair and Gladiolus Days. Here, you can explore the Gainey-McCarthy Schoolhouse, the Hill sisters’ log house, and an early log barn, getting a feel for the agricultural heritage of Winona County. Admission here is free with a $5 suggested donation.

7. Watch a Performance at the Great River Shakespeare Festival

The Great River Shakespeare Festival (GRSF) is a popular summer event for anyone who loves theater. Set against the stunning backdrop of Winona’s bluffs, the festival offers 3 shows; but it’s not just about the plays.

There are ice cream socials, talkbacks, and various events that make it perfect for a fun weekend with friends. 

The actors at GRSF are incredibly talented, and every detail of the performances, from costumes to lighting and sets, is carefully crafted for an amazing experience. 

GRSF is an important part of Winona’s arts and theater scene. The plays and performances are stellar, and the festival also has a variety of music, art and other events, including an annual global sonnet contest.

GRSF is open during the summer season only, so plan your visit accordingly.

8. Bike the 5-Mile Trail through Lake Park

a walking trail in Lake Park in Winona
Walking along the trail at Lake Park is one of the most relaxing things to do in Winona. |Photo by Amy Torbenson from Unsplash

If you love biking or walking, Lake Park is the go-to spot with its 5-mile leveled trail. The trail goes around the lake and through Lake Park, giving you views of the park, the nearby bluffs, and other parts of the town. 

It’s a popular place, so you’ll see walkers, cyclists, and even in-line skaters, so keep an eye out! If you’re walking your dogs, please note that dogs are allowed in West Lake Park but not in East Lake Park. 

9. Relax on the Winona Tour Boat

Hop on the Winona Tour Boat at Levee Park for an 1.5-hour journey that’s both fun and educational. As you cruise the Mississippi River, you’ll be treated to stories about Winona’s history and its connection to this famous river. 

Don’t forget your camera and binoculars – there’s a lot of wildlife to spot, including eagles, deer, turtles, and even beavers! The tour is guided by experts like former boat captains or wildlife authorities. 

You’ll learn about the river’s navigation channels, the lock and dam system, and see different types of boats and barges that use the river. 

Running from April through October, it’s perfect for all ages, with tickets at $19.95 for adults and $10 for kids aged 5-17. Little ones under 4 join for free. 

Plus, there’s a service bar on board where you can buy snacks and drinks. It’s also available for private parties. 

10. Admire the Architecture at The Basilica of Saint Stanislaus Kostka

the exterior of Basilica of Saint Stanislaus Kostka
The Basilica of St. Stanislaus Kostka is a prominent landmark in Winona, and a nod to the town’s Polish heritage. | Photo by Tom Fisk from Pexels

The Basilica of Saint Stanislaus Kostka is not just a church; it’s a masterpiece of architecture in Winona and designed in Polish Cathedral style.

When you step inside, you’ll be stunned by the stained glass and the giant pipe organ that fills the space with music.

It’s the oldest Catholic Church in the city, steeped in history, and it’s been recognized nationally since 1984. 

Whether you’re into history, architecture, or just looking for a peaceful place, this basilica is a spot you can’t miss.

11. Travel to Europe at the Garvin Heights Vineyard

Next on the list of the best things to do in Winona MN is Garvin Heights Vineyard. Here  you can taste the rich wine traditions of Europe with a local twist. Set on a bluff above Winona, this vineyard offers great views of vineyards and rolling ridges. 

It’s the perfect place to enjoy award-winning wines and ports made from locally grown grapes, along with delicious local cheeses. The vineyard’s friendly atmosphere makes it ideal for family gatherings, meetings, or social events.

At Garvin Heights Vineyards, you’ll experience wines produced from cold climate grapes grown right on their farm, adding a unique local flavor. 

They offer wine tastings in flights, allowing you to sample 4 wines of your choice from their weekly selection. The tasting fee is $8.00, but it’s free if you purchase 3 bottles of wine. This vineyard is a great place to relax, enjoy good conversation, and savor the taste of local wines. 

12. Learn about the Legacy of J.R. Watkins at Watkins Heritage Museum & Store

The Watkins Heritage Museum & Store that takes you through the 149-year history of the Watkins Company. It’s a great spot to learn about the company’s journey to become a household name in personal care products, with displays of old products, advertising, and photographs. 

Admission to the museum is free! Connected to the museum is the Watkins Store, where you can buy over 350 different Watkins products, including their famous Vanilla and Liniment.

The museum is very informative, and the store offers a great selection of products to purchase. Don’t miss the company timeline, which highlights best sellers from different decades. It’s a glimpse into a company that has been a part of American homes for generations.

The museum and store are open from 10 am to 4 pm Monday through Friday, and 10 am to 2 pm on Saturday, but they’re closed on Sundays. Keep an eye out for special items and historical tidbits that tell the story of Watkins’ evolution over the years.

13. Step into the Past at the Pickwick Mill

Built between 1856 and 1858, the historic Pickwick Mill, is one of the oldest flour mills in southeast Minnesota. It’s recognized as being the 1st commercial flour mill west of the Mississippi River. 

Constructed from locally quarried limestone, the mill initially served as a sawmill before transitioning to a flour mill. During the Civil War, the mill operated 24/7, producing 100 barrels of flour daily for the Union Army. 

Post-war, it became a key flour-milling center for southern Minnesota and parts of Iowa and Wisconsin. A visit here is like stepping back in time. 

The mill charges $10 for adults and $3 for children, but note that it doesn’t accept credit cards. It’s open from 12 pm -5 pm, Wednesday to Sunday, from May through October, and you can also visit by appointment on non-operating days. 

When you visit, look out for the mill’s original features and machinery, which provide a rare look into the 19th-century milling technology.

Final Thoughts: Best Things To Do In Winona MN

an overview look at Winona Minnesota
Winona maintains its small-town, Midwest charm, which makes it a great place to stop on a Midwest road trip. | Photo by Tom Fisk from Pexels

Winona is a well-kept secret that offers a blend of natural scenery,  history, and family fun. 

Explore the past at the Winona County Historical Society, enjoy the arts at the Great River Shakespeare Festival, or admire the unique exhibits of the Minnesota Marine Art Museum. From the stunning vistas of Sugar Loaf Bluff to the activities on Lake Winona, this small town is big on adventure.

So, if you’re traveling around Minnesota, make sure to make a stop at this charming town, because there are surprisingly a lot of things to do in Winona, MN!

Do you have a question or comment about any of these things to do in Winona MN? We’d love to hear from you! Leave your thoughts in the comments below.

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About the author of this guide to the best things to do in Winona MN: Based in the San Francisco Bay Area, Shreeyeh Rajan runs a California travel blog that focuses on a variety of California destinations. She provides helpful travel tips, guides and itineraries, making trips easier for her readers.

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