Traveling almost as far south as you can get along the Great MN River Road, you’ll run into the fun town of Winona. This small town has a mix of fun hikes, community lakefront paths, epic playgrounds, scenic bluff country, and picturesque views of the Mississippi River. There are tons of fun things to do in Winona MN.
Come on the weekend and enjoy a farmers’ market in the downtown area and get a real feel for the town. You could easily spend a weekend exploring the many things to do in Winona.
My first recollection of Winona MN was from the Country Singer Wynonna Judd. While she got her name after the town of Winona AZ, it still put Winona on the map for me. I always wondered what was hiding in the riverside town a few hours southeast of Minneapolis.
The allure started to grow as I started to hear about the fun things to do in town, like the infamous Sugar Loaf Bluff and Mississippi River cruises. This Memorial Day, I had to experience it for myself.
Winona Minnesota located in southeastern Minnesota is called an island city because a good portion of it is an island on the Mississippi River. It was founded in 1851 by a steamboat captain and grew during the lumber mill days.
Today you’ll see many historic buildings as you go through town. This small Minnesota town is just minutes away from La Crosse and even his home to Winona State University.
Fun Things to Do in Winona Minnesota
Breakfast at Bloedow’s Bakery
There are some bakeries in town that everyone knows about. Bloedow Bakery is one of the best places to be in Winona MN. The bakery started in 1924 and has continued to use the same recipes.
The bakery is open Mondays – Fridays from 6 am-3 pm and Saturdays from 7:30 am-2 pm. The secret is definitely out in this place.
We scheduled our Day Trip to Winona MN specifically on Saturday to visit it. Unfortunately, we got there a few minutes after they opened to find a line around the block. We decided to try again later in the day only to find the same results.
Spend some time at Levee Park next to historic downtown Winona. One of the best things about visiting a river town is Levee Park.
Sitting along the Mississippi River in southeastern Minnesota, it’s the perfect place for a picnic, or just to chill with your morning coffee.
Levee Park in Winona also has a multi-use trail that is beautifully maintained. The Levee Park Boulders are perfect for letting the kids let loose. Located behind Island City Brewing Company, the two boulders are set up to test your climbing skills.
During the summer the park hosts an outdoor Farmers Market filled with all kinds of great treats, food, and music.
We were able to pick up breakfast at Go Boy Dough, Bread & Pastries, and fresh coffee at Carlson Roasting Co. In downtown Winona, this is the spot to be on a Saturday morning.
Garvin Heights Overlook
For a view of Winona from above, do the scenic drive to the Garvin Heights Overlook. The mile-and-a-half road takes you up the bluff side, to the scenic overlook of the Mississippi River Valley below Lake Winona.
If you are looking for a cycling challenge, Tour de France winner Greg La Monde trained on this road which climbs 540 feet in 1.15 miles with a grade of 9.2%. The overlook is also accessible by foot.
There is a gravel parking lot at the base of the park, along with some stairs taking you to the top. My original plan was to hike to the summit. But google maps took me almost all the way there. Great spot to show the kids the city of Winona from above.
Sugar Loaf Bluff
I’m not going to lie, seeing Sugar Loaf bluff off in the distance in Winona is a little intimidating. I wasn’t even planning on hiking it until my planned hike up Garvin Heights was a bust. With a few hours to spare, we decided to tackle it.
Sugar Loaf Bluff towers 500 over lake Winona below. The pinnacle rises more than 85 feet above the bluff. The limestone rockface makes for a popular destination for rock climbers.
Once you reach the summit, there are additional trails wrapping around the base. Take some time to explore this spectacular feature.
From up here, you’re looking at the best scenic views of Southeast Minnesota.
If you are only going to do one hike, this is the one to do. It’s a steep climb, but easy enough for the entire family to do.
Google Maps takes you right to the trailhead in front of Edina Realty. The trailhead is right behind the parking lot of the building. Make sure to park on the side of the road, and not in the business parking lots.
Give yourself an hour to hike up there, and explore and another 15 minutes to get down. It’s a must-see attraction.
I wished we had brought our trekking poles on this trip, they would have been helpful.
Winona Lake Park
Lake Winona is sandwiched between the Mississippi River and the bluffs, split in half by a land bridge. Around the lake is a 6-mile trail commonly used by bicyclists. The bike paths get a lot of traffic, so keep an eye out.
You can also stop at the park’s bandshell and catch a concert and let the kids go to the park, aptly named ‘Every Kids Dream Park’. This was such a great place to let the kids get their energy out. It was hard to pry the kids away.
While they were playing, my husband and I meandered over to Memorial Park. Almost every town has a Memorial Park but few have truly inspired me. This particular one had some of the best monuments, one for each of the different wars.
Minnesota Marine Art Museum
The Minnesota Marine Art Museum may be the best museum in MN. The Museum features collections that emphasize water themes but are more than boats.
There are two collections you gotta see. First is the American Collection. It features Washington Crossing the Delaware, and Commerce of Nations Rendering Homage to Liberty. The painting was used to help generate funds for the base of the Statue of Liberty.
In the European Collection, there were works by Vincent Van Gogh, Claude Monet, Pierre Auguste Renoir, and Pablo Picasso.
There was also a Landscape, “Seated Man”, a study piece for “A Sunday Afternoon on the Island of La Grande Jatte” by Georges Seurat.
Never had I seen so many famous works of art all in the same room. I had to scour through the rooms at the Smithsonian, of only a few of them.
If you have kids, I recommend picking up their free Overboard Scavenger Hunt at the main desk. They have it for all difficulty levels. It kept my kids engaged in finding specific elements in the paintings.
They can turn in their bingo sheet for a prize. The museum is open Monday – Sunday from 10 am – 5 pm. Admission is $9 for adults and $3 for students.
I highly recommend stepping inside. While everything may have a water theme, it by no means is a bunch of paintings of boats!
Lunch at Lakeview Drive-Inn
Lakeview Drive-Inn is Winona’s oldest restaurant, opening in 1938. Pulling up, you get the feeling you’ve gone back in time, minus the poodle skirts.
The homemade root beer is served in old-fashioned frosted mugs. Food is made to order and sits window side. Outside are tables to dine on and the service is exceptional.
Behind you is a view of Sugar Loaf Bluff and the shore of Lake Winona. This place is truly a fun experience.
Lock and Dam No. 5
Just north of Winona is Lock and Dam No. 5. There is actually one closer to town (Lock and Dam No. 5a) but is on the Wisconsin side.
My fascination with Lock and Dams started sometime last year. I’m not sure what fascinates me most about them. The raw power they produce or the ingenuity of people.
One day, I might get on a canoe and finally paddle my way down the Mississippi River as Eddy Harris did in his book Mississippi Solo. For now, I’m sticking with watching them from the viewing platforms.
The Lock and Dam are accessible from Highway 61 northbound. The viewing platform puts you right next to the action. The lock is 110 feet wide by 600 feet long.
On a busy weekend day, the lock is in constant use with recreational boats making their way down the river. It takes about 15 minutes to fill or empty a lock chamber.
There are a couple of other great Lock and Dams You can view:
Mississippi River Lock & Dam Number 2 in Hastings MN
Things to do at or near Mill Ruins Park in Minneapolis
Hike John A Latch State Park
Are you ready to hike 585 steps, up 450 feet to the most rewarding overlook? John A Latch State Park is where to go. The park is 12 miles northwest of downtown Winona in the city of Minnesota City.
Unlike most of the MN State Parks, this is just a blip but sits on an exceptional piece of property. The park has a parking lot for about 8 cars. Onsite is a single picnic table and firepit, with no overnight camping. But the real reason for going is the hike.
The only trail in the park is 98% stairs. All the way up the side of the bluff. At the 100-step mark, you’ll get to a set of benches. During the exceptionally steep sections, you’ll find handrails to give you a helping hand.
Don’t be surprised to see a few people stopped in place on the assent. At the top, you’ll be rewarded with the best view of the shore of the Mississippi River.
Consider spending the night. There are a number of great hotels in the area. You can book one by clicking here.
Paddle the Backwaters of the Mississippi River
Experienced paddlers will love the opportunity to paddle through some of the backwaters of the Mississippi River. Thymically speaking it’s a floodplain forest. There are plenty of islands to paddle through. You can also take the Verchota Canoe Trail.
It’s 11.3 miles through some stunning areas of the Upper Mississippi River National Wildlife & Fish Refuge area. If you are looking to rent a watercraft, check out Prairie Island Campground. You don’t have to stay there to rent equipment.
Garvin Heights City Park
Garvin Heights City Park is a large public park. The park includes a basketball court, a playground, a baseball diamond, a picnic area with grills a pond, and a football field.
The property also includes a 1.5-mile walking trail that leads to the top of Garvin Hill, which offers excellent views of the city and river valley.
Garvin Heights Vineyards
Garvin Heights Vineyards is located in Winona Minnesota, just north of the city. The winery is family-owned and operated, and its wine is made from grapes grown on its 160-acre estate. They offer a variety of wine tastings, as well as gift baskets and wines by the bottle.
The winery was started in 2000 by Bob and Lisa Rossetti. They grow their own grapes and make their own wine. They have a small vineyard with about forty acres. They produce fruit wines, sparkling wines, ports, and a few red wines.
Great River Bluffs State Park
Great River Bluffs State Park is a great park a few miles south of Winona. The park has a great hiking club trail, with miles of other hiking opportunities. There is a small river that runs through the center of the park, with plenty of sites for campers.
Polish Cultural Institute
The Polish Cultural Institute in Winona, Minnesota started in 1983.
It promotes Polish culture with events, education, and exhibits. It also helps Polish-Americans with language lessons, library services, and cultural resources.
Stop in and see what’s going on.
Great River Shakespeare Festival
The Great River Shakespeare Festival happens every summer in Winona, Minnesota. It’s a fun event that attracts theater enthusiasts from across the US.
The festival mixes classical and modern plays, delighting the audience with professional actors who perform Shakespeare’s works. Young actors from the Shakespeare Academy also perform.
Workshops, live music, and discussions with actors are some of the exciting events at the festival. It’s a chance for people to gather and enjoy the pleasures of theater.
C. A. Rohrer Rose Garden
The C. A. Rohrer Rose Garden in Winona Minnesota is one of the most beautiful and inviting rose gardens in the Midwest. The garden was designed by C. A. Rohrer, who was a noted horticulturist and rose breeder in the early 1900s.
The garden features more than 2,000 different roses, many of which are rare or hybrid varieties. In addition to roses, the garden contains peonies, lilies, Forget-Me-Nots, Statice, delphiniums, and other flowers. It is a peaceful place to relax and enjoy the beauty of nature.
Tews Corn Maze
Tews Corn Maze in Winona Minnesota is operated by The Family Fun Center and it is open from September through October.
The maze features over 20 acres of twists and turns and is sure to keep your family entertained for hours on end. There is also a farm, a petting zoo, and a Mini Golf course to enjoy while you’re there.
The Watkins Museum is a small museum that preserves the history of the Watkins family.
The museum has a collection of art, artifacts, and photographs documenting the life of the Watkins family from the 1800s to the present.
The museum also has an exhibit on the history of Winona and the Watkins family.
Cedar Valley Golf Course
The Cedar Valley Golf Course is a championship golf course that is sure to please any golfer. The fairways are wide and smoothly maintained, while the greens are true and offer plenty of opportunities to score well.
The clubhouse is excellently maintained and staffed, making it easy to get all the information you need before your round.
Big Valley Ranch Inc, Riding Academy
Big Valley Ranch Inc, Riding Academy offers horseback riding lessons for all levels of riders.
Offering both indoor and outdoor riding, the academy has a variety of horses and trainers to choose from.
Lessons are available for all ages, and members can also use the center’s facilities for group rides and private lessons.
International Owl Center
The International Owl Center in Winona, Minnesota is home to over 100 owls, including bald eagles, golden eagles, and great horned owls.
The center educates the public about owls and their importance to the environment.
They also provide wildlife rehabilitation services for injured and orphaned owls.
Ride the Paddle Boat American Queen Voyages
The paddle boat ride on the Winona River is a fun and easy way to spend a summer day. The river is wide and calm and there are no tides so you can go as fast or slow as you like.
The boat operators are friendly and will give you some history of the area while you are on the river.
Would I go back for more fun things to do in Winona MN?
I had such a great day trip to Winona MN, I wish I could have spent the weekend. Unfortunately getting a campsite on Memorial Day Weekend was next to impossible.
Winona is known for its picturesque views, and it didn’t disappoint. Thankfully I’ve got another trip lined up this summer to do some more exploring.
I would love to kayak on the Mississippi River when I visit Winona again. I also need to get down to Great River Bluffs State Park and do their hiking club trail.
If time permits you should also check out the Winona Tour Boat, for a ride on the Mississippi River. That is going to have to wait until this fall though.
We somehow timed our trip with perfect weather that let us do not one but three hikes. I will be back for more things to do on my next drive down the Great River Road. Have a great time!