Awesome Fall Things to Do in Winona, Minnesota

Winona Stuns in the Fall
If you’re coming from the Twin Cities area, I recommend you take the scenic route on Highway 61 south, on the Minnesota side, on your drive to Winona. Then, on the return trip, take highway 35 on the Wisconsin side so you’ll get great views of the Minnesota bluffs. Read on for a roundup of some of our favorite things to do in Winona!


1. Kick Off Your Day with Coffee
To get the day started,d visit Blooming Grounds Coffee House, located in the heart of Winona. They have a great selection of cappuccino, lattes, chai tea, and smoothies. If you’re hungry, try a breakfast burrito, quiche, scone or bagel! They have a large indoor space with tables and chairs, and there is a small outdoor seating area as well.


2. Visit the Minnesota Marine Art Museum
We kicked off the day with the Minnesota Marine Art Museum. It’s a gorgeous building next to the Mississippi River with pretty gardens. The museum had many different rooms and included a chair from the Titanic as well as handwritten letters from a survivor. Another room had incredible photographs of animals underwater, like alligators, sharks, and whales. My favorite room had colorful paintings from Picasso, Mattise, Renoir, Degas, Monet, Van Gogh, and other infamous artists. I highly recommend this museum, which costs only $9! It also had a very cute gift shop in the front entrance.


3. Grab Lunch at Acoustic Cafe
After the museum, we drove over to the Acoustic Cafe. They serve sandwiches, soups, smoothies, and coffee. Order you soup and sandwiches at the counter, and either eat inside or order it for takeout and bring it over to Island City Brewing, which is just one block away.


4. Enjoy Beer at Island City Brewing
Island City Brewing has a great selection of beer! My favorites are the Octoberfest and red ale. They also have plenty of indoor and outdoor seating, and the outdoor area has a large tent, which was nice because it did drizzle for a little bit.



5. Hike Sugar Loaf Bluff and Garvin Heights
If you can only do one thing in Winona, it should be Sugar Loaf Bluff. It takes about 45 minutes round trip, including time for photos and stopping to enjoy the view along the way. The fall colors were so pretty and the view is expansive.
Pro tip: It’s really hard to find on Google Maps and the Sugar Loaf Historic Site is not the right spot. There is an Edina Realty at the trailhead, so search for that and you’ll find plenty of street parking. Once there, it will be clear where to go and you’ll see signs for the trailhead.
Another very popular hike with fabulous views of the river is Garvin Heights, just down the road from Sugar Loaf Bluff. This hike is also extremely steep on the way up the bluff, but the views make it worth it! While the hike is extremely steep, there is an easier option. If you prefer to drive, take the winding 1.5 mile road to the top of the bluff to the Garvin Heights Scenic Overlook.

6. Enjoy Donuts and Pastries
For an afternoon pick-me-up, you’ll want to check out Bloedow’s, a bakery that’s been in business since 1924! In the early 2000’s Krispy Kreme tried to set up a shop in Winona. But locals had no interest in the chain and remained loyal to Bloedow’s, sending Krispy Kreme packing two years later. Bloedow’s has remained an important staple in the community for generations, and they’ve even won an award for the best donuts in Minnesota!

7. Take a Stroll Through Lake Park
Walk or bike around Lake Park, which gives stunning views of Lake Winona. You’ll also find picnic tables, playgrounds for children, disc golf courses, ice rinks, and plenty of benches to relax and enjoy the view. The Winona Visitor Center is on the north end of Lake Winona. They’re open seven days a week from 10 am to 4 pm and can help answer all your questions about Winona. You can also purchase a day pass, which gives you access to kayaks, canoes, lawn games, and stand-up paddles boards.


8. Drive to Latsch Island
Winona has two islands that are part of the main city, so if you’re looking for a different perspective of Winona, you’ll want to check this area out. Drive across the Winona Bridge and into Latsch Island, where you’ll find a beach, picnic tables, and boathouses. Some of the boathouses are pretty basic, and some are quite elaborate. Most of them have been passed down for generations, and they certainly make for a unique site. Continue driving down the only road on this island and you’ll encounter the Historic Wagon Bridge, which gives way to beautiful views of the Mississippi River. You can walk or drive across this bridge. On the other side of that bridge, you’ll find another island and the entrance to Aghaming Park. This park is nearly 2,000 acres of floodplain forest and is a fantastic location for bird watchers!


9. Transport Yourself to Italy for Dinner
Winona has a lot of restaurants so it may be hard to choose a good dinner spot. However, if you’re looking for high-quality Italian food at a great price, and with a unique story, Sapori di Sicilia is the spot for you! The owner and chef trained in Italy and did a fabulous job bringing a slice of Italy back to Minnesota. All the kitchen equipment was brought in from Italy and the cafe is designed to replicate Italian cafes. They make fresh bread and pastries daily and offer wine from Italian vineyards. I enjoyed a delicious and light red wine from Sicily for just $5! The artwork is images of Italy from an Italian photographer, and even the music playing is streaming in from a radio in Sicily. It’s a very thoughtfully curated experience and one that I highly recommend.


10. Finish the Night at No Name Bar
No Name Bar is a quirky place that has literally never officially had a name, although if you do a quick Google search, you’ll find they sometimes go by Ed’s No Name Bar. There is no signage on the front of the building and it looks like an uninviting space from the street, but once you walk in, you’ll be greeted by live music and friendly bartenders. The owners work to get musicians that are otherwise just passing through the area to perform in larger cities. Because of the clever idea, they’ve ended up with internationally recognized musicians, some of who have even won Grammy’s. The vibe inside is laidback yet edgy with a hipster feel. You’ll find unique artwork, a stage for musicians, and antique pinball machines. Â It’s certainly a unique stop!


11. Rest and Unwind at Fairfield Hotel
While visiting Winona, we stayed at the Fairfield hotel across the street from Sugar Loaf Bluff. It’s clean and centrally located, and it offers free parking and free breakfast. While this hotel is not within walking distance of the downtown area, it’s just a short drive to the restaurants, hikes, museums, and parks mentioned above. It’s also surrounded by gas stations, fast food, and big-box stores, like Target, Walgreens, and Menards, so if you forgot to pack something, it’ll be easy to get what you need.

You Won’t Regret a Trip to Winona
There are so many great things to do in Winona, you definitely won’t regret visiting this small, beautiful town. While the bluffs are stunning in the fall, I think Winona is a beautiful town year-round. Those fall colors really provide an extra special experience. Looking for more ideas? Check out my post on epic things to do in Stillwater!


You May Also Like

18 Free Things to Do in the Twin Cities
July 26, 2022
9 Epic State Parks Along the North Shore
June 7, 2021
10 Comments
MK Dymock
The photos are so gorgeous. I love how green it is. What a fun place to visit.
Kristen Glazer
I can’t wait to go back, it is a beautiful town!
Josy A
Winona looks fabulous! I can see why you liked it, especially with the walk to Sugar Loaf Bluff! The long drive sounds really pleasant too (even if the trees had not yet changed colour completely!)
p.s. Is that your mum and dad with the beers? Yay for getting your parents involved with your blogging. 😀
Kristen Glazer
Those are my in-laws. Our daytrip to Winona was their idea! They have come up with some great ideas for my blog 🙂
Karen
When I lived in Minnesota, I never made it to Winona. This looks like a small city that would make a fun visit. Is this the city where they make Winona canoes?
Kristen Glazer
I’m not sure about the Winona canoes, but I do know Winona Ryder is from this town!
Tara
Such a cute town! I love the idea of taking day trips around the state. Also, I’d probably spend the whole day at the museum!
Kristen Glazer
It was a fantastic museum! I’d like to go back.
Susan
Winona is such a cute spot! Def need to spend more time and there and check out the Sugar Loaf hike!
Kristen Glazer
You would love that hike!