Winona with Kids: Spend 2 Exciting Days Exploring as a Family

This post, featuring my 2-day itinerary for Winona, Minnesota, with kids, may contain affiliate links. It was also sponsored by Visit Winona. All opinions are my own. For more, please read my Disclaimer & Disclosure Policy.

A father and his young daughter walk along a paved path in Winona.

Looking for a great weekend getaway that feels a little different (and definitely underrated) in Minnesota? Spend the weekend exploring Winona with your kids! I promise, you’ll be impressed with what this river town in Southern Minnesota has to offer (we were!). Just about two hours from Minneapolis, Winona is packed with fun things to do with kids. Spot soaring eagles atop scenic bluffs. Meander through beautiful art galleries along the river. And, get ready for a truly hard-to-beat food scene. You also can’t miss strolling the walkable downtown (it’s filled with cute shops!).

Winona is the perfect mix of outdoor adventure and relaxed exploring. Here, you can take things slow and focus on what really matters-the time spent together. And, this itinerary will have you doing it all! I’ve included all of our favorite stops, plus plenty of the best places to eat and where to stay in Winona for families!

Day 1 in Winona with Kids

Get ready for a fun mini road trip to Winona with your kids! This destination in Southern Minnesota is so charming and fun. After you check into your hotel, get acquainted with Winona’s beautiful trails and dynamite food scene. This itinerary has you arriving mid-day (after lunch, but before hotel check-in). If you’re wondering how to spend a weekend in Winona, Minnesota, this is where to start!

Explore the Flyway Trail

A man and his young daughter walk along the Flyway Trail.

Start your Winona adventure on the multi-use Flyway Trail with your kids. This scenic, easy path is perfect for walking or biking. Along the way, enjoy beautiful water views, tons of birds, and even huge snapping turtles (if you’re lucky!). We saw about 5 or 6 snapping turtles in the water! They were absolutely massive!

A father and his young daughter look at the water while walking along the Flyway Trail in Winona.

The trail starts in downtown Winona (near Levee Park). If you want a shorter, more contained (car-free) trek with your kids, you can limit your exploration to the Flyway Trail Winona Connector (there is street parking inside Aghaming Park Preserve). Either way, it’s an easy trail to make, as long or as short as you have the stamina for during your visit!

Kids will love crossing the bridges and looking to see what birds and critters they can find. Plus, you can also watch any passing trains, too! The friendly energy from the other bikers, hikers, and bird watchers also makes this local spot feel lively and fun the whole way! No wonder this is one of the most family-friendly things to do in Winona.

Post Hike Drink from Blooming Grounds Coffee House

Three hands hold out refreshing drinks from Blooming Grounds Coffee House in downtown Winona.

After your hike, head downtown to Blooming Grounds Coffee House. One of the best restaurants in downtown Winona with kids, it’s super cute! And, a very popular spot. Expect a bit of a wait, but the stop is well worth it! You can select from coffee, refreshers, or a quick post-hike snack. We loved the refreshers, which come in tons of fun flavors! The bakery case was still pretty full in the afternoon, too, so you’ll have lots of snack options.

With plenty of seating and an extensive menu, it’s the perfect place to relax or kill time before hotel check-in. If you’re hungrier than just a quick snack, they also offer a great all-day menu filled with sandwiches, wraps, salads, and more.

Check into Hotel 44° North

Cozy beds in a suite in Hotel 44° North.

Check into Hotel 44° North for a stay that makes exploring Winona with kids feel even easier and more fun. This new-ish, very comfortable hotel has an unbeatable, walkable downtown location and beautiful river views. I highly recommend booking your weekend stay here!

Our Double Queen Suite with Kitchenette even had a semi-seperate living space, which gave us plenty of room to spread out. It included a small table and a couch with a TV area. And, the balcony was such a bonus! Add in the complimentary breakfast and the cozy bar for a nightcap, Hotel 44° North really felt like a home base you’ll actually want to hang out in.

The indoor pool area with a hot tub and sauna at Hotel 44° North.

The amenities are a big win for families, too. The indoor pool is large and perfect for kids to burn off any extra energy after a day of exploring. If parents don’t join in on the pool action, they can relax on one of the many loungers. Or, sneak into the sauna or hot tub. All three are in the same space. There is also a nearby fitness room. Hotel 44° North is undoubtedly one of those hotels where both kids and adults are equally happy (which is always a win on a family trip!).

A Few More Kid-Friendly Hotels in Winona, Minnesota

Looking for more kid-friendly hotel ideas in Winona? Here are a few fantastic alternative places to stay in Winona for your upcoming family visit!

Grab Takeout from Heirloom Seasonal Bistro + Enjoy Live Music at Two Fathoms Brewing Company

For one of the best places to end your first day and eat in Winona with kids, grab takeout from Heirloom Seasonal Bistro in downtown. It’s just a quick, easy walk from the hotel. It’s casual with a fresh, thoughtful menu. And, you can order ahead online if you want to do takeout, like we did. You can absolutely dine in, too, but we loved the flexibility of taking it to go for a more laid-back evening at a nearby brewery with live music.

Take out and live music at Two Fathoms Brewing Company.

Then head over to Two Fathoms Brewing Company. It’s one of the most fun, family-friendly things to do in Winona at night. You can bring your food right in, grab a table, and enjoy live music (especially on weekends) or another event. We got to enjoy music from Jackie Treehorn & The Malibu Sheriffs over dinner, which was such a hoot! They are phenomenal.

Kids will also love the games and small play area. They also offer a small pizza menu and snacks if you prefer to order on-site. With a patio, rotating events, and a cool historic setting, it’s an easy win for everyone. Be sure to check the events calendar to see what’s on before heading to Winona!

Then, it’s a quick walk back to Hotel 44° North to end your first day in Winona.

Day 2 in Winona with Kids

After a good night’s sleep, here’s how to spend day 2 of your visit to Winona with kids. Today is all about enjoying uniquely local experiences, eateries, and downtown Winona. Feel free to take the morning slow! There’s no reason to rush. Everything is located within close proximity.

Start Your Day with Coffee + Pastries from Cafe Sapori di Sicilia

A family picks out pastries from Cafe Sapori di Sicilia.

Start your day at Cafe Sapori di Sicilia. This low-key spot has a timeless feel, with incredible coffee and some of the best pastries we’ve had in Minnesota-flaky, buttery, and absolutely delicious (the blueberry cream cheese one was my favorite!). It’s the kind of place where you’ll want to linger, but it also works great for a quick, easy start to your morning if preferred. When we were there, there was even someone playing the piano. The whole experience was just lovely, and I truly think this is one of the best places to eat in Winona with kids.

A table with pastries from Cafe Sapori di Sicilia.

Everything is made in-house, staying true to their authentic Sicilian roots. Beyond pastries, the menu includes sandwiches, salads, and even gelato, making it a great option any time of day. Whether you’re grabbing a quick breakfast or planning to come back for lunch, it’s a delicious stop in the heart of Winona.

See the Water-Themed Galleries at the Minnesota Marine Art Museum

A family looks at paintings at the Minnesota Marine Art Museum.

After breakfast, head to the Minnesota Marine Art Museum. It is one of the most beautiful and kid-friendly art museums we’ve been to. It genuinely felt designed for families to have fun and enjoy the galleries together.

A young girl completes the bingo program at the Minnesota Marine Art Museum.

Set right along the river, the views alone are worth it-but inside, it’s just as impressive. The galleries all connect to water, maritime history, and marine life in creative ways. And, they’re thoughtfully curated so it feels engaging, not overwhelming (even for littles). The bingo program was a huge hit for our family (and came with fun prizes!). There are even three levels of difficulty to choose from, so everyone can participate. The friendly staff made the experience even better. They provided such incredible insights and were so kind to my daughter.

Beyond the art pieces, there are interactive areas and cozy kid spaces with books and small toys. Once you visit, you will quickly see why this is one of the most fun indoor activities for kids in Winona. Plus, the museum has a fantastic gift shop to browse before you leave.

We also loved grabbing lunch on-site (that’s next!).

Lunch at the Waterbar Cafe

A BLT for lunch from the Waterbar Cafe in Winona.

Enjoy lunch together at the Waterbar Cafe. It’s one of the best places to eat lunch in Winona with kids-especially if you’re already visiting the museum. Tucked inside the Minnesota Marine Art Museum, this intimate spot offers beautiful river views and a relaxed, welcoming atmosphere that makes it easy to take a break with kids. They can even get up and wander a bit while you eat if they need to move.

The menu is small but mighty, with a few sandwiches, soups, and pastries. Plus, they offer a mix of coffee, tea, and even wine or beer for adults. I highly recommend the warm roast beef. It was SO good, and perfect after a morning of exploring. It’s an easy, delicious stop that feels a little elevated without being fussy.

Explore Downtown Winona

A family walks along historic Downtown Winona.

Spend some time exploring downtown Winona. You’ll love the historic charm, with brick buildings and wide streets. There is plenty to discover around every corner in downtown Winona. It’s super walkable and filled with local shops that make browsing feel like part of the adventure.

A dad and his young daughter walk along the sidewalk in Downtown Winona.

We especially loved popping into Yarnology (a must if you have a little knitter like I do!). Then, Chapter 2 Books is a cozy used bookstore packed with everything from kids’ books to graphic novels. You’ll also find cute boutiques, plants, and unique gifts throughout downtown.

Downtown also has tons of eateries nearby and easy access to Levee Park for river views and a shopping break. It’s a perfect way to slow down and explore more of Winona’s vibrant community with your kids.

Grab an Afternoon Treat from Nate and Ally’s

A girl spoons ice cream out of a cup from Nate and Ally's.

While downtown, grab an afternoon treat from Nate and Ally’s. This ice cream joint is bright, fun, and an instant hit with families. Whether your kids love frozen yogurt, custard, or something in between, there are tons of options to choose from. If you’re looking for the best places to get ice cream in Winona with kids, add this one to your itinerary!

A man serves his own ice cream selection at Nate and Ally's.

When you arrive, you can select a cup size and then your preferred flavor. Choose from frozen yogurts, custards, and other ice cream types. There are tons of flavors to choose from! Kids will love the chance to dish their own cups, each with an individual handle for its flavor. The real highlight, however, is the topping bar-with over 50 choices! Kids can build their own frozen masterpiece (which is half the fun). My daughter is still talking about this place!

You can also try their Mix-It creations or even edible cookie dough for something different. It’s the perfect sweet stop while exploring downtown Winona (and a guaranteed crowd-pleaser!).

Walk Around Lake Winona

A couple walks together on the paved path around Lake Winona (the big lake).

Get out of downtown for a bit and walk around Lake Winona. Locals call it “the bike path,” but it’s perfect for walking, scootering, or biking, as you prefer. The route is a smooth, paved trail with beautiful views the entire way.

A man and his young daughter stand on a dock, taking a break while walking around Lake Winona (the small lake).

You don’t have to do the full loop (about 5.5 miles). You can easily just pick a section that works for your family and enjoy the fresh air. If you start at the Visitor Center, there is a small parking lot, and you can easily walk around the small lake or the big lake. That said, there are parking options on both sides of Lake Winona, making it easy to choose routes and experiences.

Along the way, you’ll find playgrounds, docks, a rose garden, and plenty of spots to stop and take it all in. The views of the bluffs are incredible! And, there’s always something to see, from boats on the water to families out enjoying the day. Keep an eye out for eagles and other birds, too! No matter how old your kids are, this is undoubtedly one of the best outdoor things to do in Winona with kids.

Drive Up to Garvin Heights Park for a Scenic Lookout

A woman enjoys a scenic lookout at Garvin Heights Park.

Drive up to Garvin Heights Park for one of the most memorable, family-friendly things to do in Winona. The blufftop views are absolutely stunning! You can see across the river valley, with Lake Pepin and even Trempealeau Mountain on a clear day. Keep your eyes open, because this is also one of the best places to see eagles soaring above Winona. It’s an easy stop with kids since you can drive right up to the overlook. I hear it’s even better at sunset!

If your crew has a little energy left, there are short trails to explore, including a stair climb and paths winding through the park. Even a quick visit feels special, with sweeping views of Winona below. It’s the perfect way to wrap up your trip on a high note (quite literally!).

Dinner at Miya Japanese Bistro

Sushi and gyoza from Miya Japanese Bistro.

End your visit to Winona with dinner at Miya Japanese Bistro. Located right downtown, this casual, welcoming eatery has something yummy for everyone in your family. Their menu features a great sushi selection and flavorful hibachi options. It’s an easy win for families (especially if you have a mix of adventurous and picky eaters!).

Two hibachi dinners from Miya Japanese Bistro.

The staff is incredibly friendly and made the whole experience feel special. You can tell they really care about the food they serve and the community. Don’t skip the onion soup! It was so good. I’d honestly go back just for that. We also loved the gyoza and steak and shrimp hibachi.

As one of the best restaurants in Winona with kids, it’s a fun, relaxed way to end the day. Not to mention, a great opportunity to share stories and memories about your favorite stops in Winona from the weekend!

More Fun Things to Do in Winona with Kids

A man and his young daughter take in the views above downtown Winona.

Looking for a few more fun things to do in Winona, Minnesota, with your kids? If you are planning a full weekend trip to Winona or want to make some changes to this itinerary, here are a few more family-friendly things in the area to consider:

Levee Park
Aghaming Park Preserve (there is a beach here, too!)
Hike Sugar Loaf Bluff (The trailhead entrance is located behind the Edina Realty.)
Polish Cultural Center & Museum
Winona County Historical Society
Watkins Museum & Store (yes, like the spices and extracts!)
Bob Welch Aquatic Center
Bloedow Bakery is iconic! Unfortunately, we missed its opening hours during our recent visit, but it’s on our list for next time!
Great River Bluffs State Park and John A. Latsch State Park are both about 20 minutes from downtown Winona. And, Whitewater State Park is about 40 minutes away.

Keep Exploring Winona, Minnesota, with Your Kids

Antonia's family walks along part of the Flyway Trail in Winona.

Hopefully, this guide helped you answer the question of how to spend a weekend in Winona, Minnesota, with your family. I’m confident that you’ll quickly see why this charming river town is so special! And, one of my new favorite Minnesota destinations with kids. From scenic trails and eagle spotting to walkable downtown shops and easy, family-friendly eats, there are so many fun things to do in Winona with kids. To help you plan, I’ve included our favorite stops, along with some of the best places to eat and stay. Whether you’re planning your first visit or already dreaming about your next trip, Winona is the kind of place that keeps surprising you in the best way. I hope you have fun exploring Winona with your kids!

Unless otherwise noted, all images within this article were taken by and belong to the blog’s author, Antonia Grant. A reminder that this post may contain affiliate links. Please read my Disclaimer & Disclosure Policy for more information.

Spend 2 Exciting Days Exploring Winona, Minnesota, with Your Kids