Itinerary Ideas

Bloedow Bakery: If your day in Winona doesn’t start with a Bloedow Bakery donut, you’re doing it wrong. It has been voted not only the best bakery in the state, but also one of the best in the entire country. Whether you go for the largest, most sprinkle-filled donut in the case or the classic maple long john, any item available is a good choice. Most people have to stop and enjoy right then and there at the exterior bench near the iconic Bloedow chef mural.

Garvin Heights Overlook: Easy to access and incredible to behold—the towering overlook showcases impressive views of the entire city of Winona, the Mighty Mississippi, the nearby Wisconsin bluffs and beyond.

Minnesota Marine Art Museum: This renowned museum on the banks of the Mississippi River showcases all “art inspired by water” and includes a beautiful permanent collection as well as unique traveling exhibits from paintings to sculptures to photographs and more.

Heirloom Seasonal Bistro: Elegant and casual American fare takes on epicurean twists in this farm-to-table Winona legend. The menu changes often to reflect the freshest seasonal items available and the creative whims of its two well-known chefs. 

No Name Bar: Probably the coolest, most authentic place in town that also happens to serve a delightful drink alongside live music! Taking in local jazz or the biggest touring act in the Midwest, the audience enjoys experiences unlike any other. Drinks like the Gold Rush, Pirate Cider, and the Pineapple Basil Rum Fizz are sure to satisfy all tastebuds. No Name’s got tons of N/A options as well! 

Hiking trails along the newly updated front side of our iconic Sugar Loaf Bluff offer adventure seekers a unique vantage point to see the city. Talk about Insta-worthy! In fact, the entire bluffs are crisscrossed with beautiful hiking and biking trails that range from gentle slopes to adrenaline-infused descents. 

If you’re visiting in the winter, you HAVE to try your hands at our Winona Ice Park—these man-made walls in the bluffs make up the second-largest ice park in the country, and enthusiasts travel thousands of miles just for this one-of-a-kind climbing. If you’re not quite ready to strap in, onlookers are welcome anytime.

After you’ve explored our land trails, it’s time to hit up the water version. Head over to Prairie Island Campground for the easiest access to Mississippi River backwater trails than you have ever seen. Didn’t bring your canoe/kayak? No problem—you can rent them for a few hours or the whole weekend at the campground store.

Grab a bite to eat to-go at the Bluff Country Co-op right downtown—their hot bar selections will take you to exotic places—and picnic at Levee Park.

The new Flyway Trail Winona Connector is perfect for a post-lunch walk or bike ride and includes use of the Highway 54 Interstate Bridge across the Mississippi River, and the John A. Latsch Historical Wagon Bridge near Winona’s unique boathouse community. Watching train traffic from above the Burlington-Northern Santa Fe railroad is a must-see for kids and adults alike.

Bicyclists of all skill levels enjoy nearly 6 full miles of paved pedestrian-only paths along East and West Lake Winona. Stop for rest while the kids continue to burn off energy at the newly-opened Every Child’s Dream Playground near the historic Band Shell.

In the summer, stop over to Lakeview Drive Inn for a classic ice cream treat, homemade root beer and smiley fries that make diners of all ages grin.

Between its culture-rich arts and its incredible outdoor recreation, Winona is a legendary playground for grown-ups. But families with kids from 2 to 20 are finding plenty of ways to indulge in perfect summer days here too, with an abundance of family fun available no matter what tickles the family fancy. Here are six things families love to do when they are in Winona:

Bike and Paddle to Your Heart’s Content 

Winona and the surrounding area are crisscrossed by a couple hundred miles of biking and water trails, including everything from scenic Lake Winona bike paths to exciting single-track trails through the bluffs, to Mississippi River backwater channels. If you want to get a little fresh air while you’re here, load up those bikes and watercraft or, better yet, travel light and rent equipment while you’re in town from Lake Lodge Recreation Center, Prairie Island Campground or Adventure Cycle & Ski.

Make a pit stop at the Winona Visitor Center to shop for a commemorative t-shirt or Winona coloring book to help the kiddos remember their epic visit to Winona. 

Reach for New Heights 

Climbing--in general--may be a no-go at your home, but here in Winona, we welcome it! From new outdoor bouldering rocks at Levee Park open 24/7 year-round, to the Winona State University Indoor Climbing Center open to the public, climbers of all ages can test their endurance and grit. WSU’s Outdoor and Education Recreation Center also offers free climbing sessions at Sugar Loaf and the Winona Ice Park, all equipment provided, seasonally.

Play for All 

Families of all abilities can enjoy the newly-opened inclusive playground at Lake Park: “Every Child’s Dream,” created as a joint project between all three Winona Lions Club groups. In addition to specialized play equipment for all, over 16,000 square feet of No Fault Safety Surface provides a solid and slip-resistant base, making it easy for children who use mobility devices to enjoy moving around on the playground.

Make A Splash 

The Bob Welch Aquatic Center is a mighty fun way to while away a summer day, with zero-depth kiddie pools, big-kid pools with diving boards, a playground, and one wicked slide to bomb for the brave among you. For a nominal daily fee, the Aquatic Center is open daily to visitors and locals alike and has plenty of green space for a picnic you tote along or a cute grub stand if you’d rather grab a snack while you’re there.

Culture Up 

Even the Minnesota Marine Art Museum has activities for youngsters, including an I-Spy game that entertains kids and teens during their time browsing the museum's galleries. For grown-ups and kids alike, the art – which spans all mediums – is mesmerizing, and a couple of hours here will fill you with wonder.

Get some Eats 

During the summer months, order a Sugarloaf Mountain burger, smiley fries, and a frosty mug of homemade root beer at the iconic Lakeview Drive-Inn for lunch or dinner.

In the Winter, grab a great wrap or panini and smoothie at Blooming Grounds Coffee House in downtown Winona.

Nate & Ally’s Frozen Treat Creations is the dream of every child and child at heart. Dozens of fro-yo flavor combinations await you, plus you get to add sweet toppings like Oreo pieces, gummy worms and whipped cream until your cup overfloweth. That’s an actual word—right?

Winona County History Center: Located in historic downtown district—also majorly worth exploring on a self-guided walking tour!--the Winona County History Center houses three floors of exhibits, The Museum Shop, the Laird Lucas Library and Archives and more. Explore the area’s past through interesting and fun exhibits, both permanent and traveling.

Watkins Museum & Store: 150+ years means they must be doing something right! Free admission to the Watkins Museum offers visitors a view into the Company’s history with displays of vintage products, advertising, pics and other memorabilia. The museum is connected to the Watkins Store that sells over 350 different Watkins products including classic Vanilla and Liniment as well as new products like Sprinkles and Bitters.

Kashubian Cultural Institute & Polish Museum: This former lumber company building is now a showcase of our area’s rich, Polish immigrant history. (Stop into St. Stanislaus Basilica to learn even more.) The upper floor of the museum also houses archives of the Diocese of Winona, complete with a collection of priest cassocks and confessionals salvaged from churches.

Stained Glass of Winona: Winona was once dubbed the “stained glass capital of the world”, and we can see why. The opulence of the lumber baron era can be seen in businesses, banks and churches throughout Winona, but the real showstopper is WNB Financial’s historic downtown building, bejeweled with stained glass shipped over from Tiffany & Co in New York City. Winona is also home to a handful of well-known, stained-glass manufacturing and restoration companies including Associated Crafts-Willet Hauser.

Windom Park Historic District: Surrounded by lovely Victorian-era homes, many of which are on the National Register of Historic Places, this city block is adorned by bright perennial gardens, a gazebo, and a historic sculptural fountain where park visitors can bask in the sunlight alongside famous Native American royalty, Princess Wenonah. The fountain’s center is a turn-of-the-century bronze statue of Princess Wenonah (“firstborn daughter”), the Dakota Indian chief’s daughter who legend says is the namesake of Winona.

Treasures Under Sugar Loaf: Where history and shopping meet! Treasures Under Sugar Loaf is a three-story antique mall featuring collectibles, crafts, and home decor. Located in the historical Bub’s Brewery building and nestled under Sugar Loaf, this unique shop cannot be missed—literally. It’s huge and red and is very visible from one of Winona’s most heavily trafficked intersections.

Two Fathoms Brewing is Winona’s only craft brewery in town, and it is absolutely worth the stop. The Two Fathoms team is unafraid to get crazy with their flavors, especially in their hard and NA seltzers that are reminiscent of drinks like a Paloma.

Cross the bridge and head into nearby Fountain City, WI to enjoy a flight at Wilbur Schmitt's Draught House, home of the Fountain City Brewing Company. Located in the Monarch Public House’s "cellar" area, this recently-renovated space still offers character galore, plus tasty beverages!

While in Fountain City, stroll over to Seven Hawks Vineyards to sample their award-winning, locally-produced wines as well as wood-fired pizzas and other sharable nibbles.

About a dozen or so Winona restaurants and bars offer unique and regionally-inspired craft beers on tap; some of our favorites include:

Brewski’s Pub & Grill: Check out their nightly Happy Hour featuring beer, wine and liquor from 4-7pm. Stay for the Maple Fire or Bison burger—all served on a Bloedow Bakery bun.

Hei ‘N Low Tap: A great variety of brews can be found in this cool, neighborhood bar. They’ve also got live music almost every weekend.

Peter’s Biergarten: Winona’s first outdoor beverage garden is located in the heart of downtown and open May-October, plus special events. Craft beer, wine and seasonally-inspired cocktails mix beautifully with the relaxed, yet big-city vibe.

Sliced: One of downtown’s newest restaurants offers rotating tap beers and unique takes on pub favorites like pizza, calzones, wings and more.

Ready to get your bike on? We’ve got everything from easy cruising to full-on marathon training. We’ll take you from 1 to 100:

Lake Winona Path Trail: The five+ mile blacktop trail runs along the south side of the city and circles both segments of the lake through Lake Park. The route is flat and easy—perfect for families or those who enjoy the chill, scenic route.

Flyway Trail Winona Connector: This non-motorized connector bridge/trail from Winona to The Flyway Trail in Wisconsin links the city to a scenic biking route via Aghaming Park, where one can see 1,950 acres of some of the best-preserved floodplain forest in the country, and catch amazing views of Latsch Island’s unique boathouse community.

Winona County Bike Loops: There are dozens of winding, off-road bike loops throughout the entire county, including many that connect to larger systems like the Mississippi River Trail and the Great River State Trail.

Holzinger/Bluffside Park: This trail is beautiful in any season, wildflowers abound in spring, and it is lovely in fall colors. These are single-track trails with a 9-mile loop, mostly expert off the ski trails and are rocky clay. Watch out for hikers and dog walkers as they are a favorite walking destination as well.

Garvin Heights Road: For the experienced cyclist who’s looking for a training challenge, the Garvin Heights climb is tough to beat. 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%. Think you’ve got what it takes?

Acoustic Café: Their Hoagie Sandwich is so epic that they have little else on their menu—besides amazing coffee drinks, of course. It’s all about those sweet yellow peppers and their “special sauce”. Don’t ask us what’s in it. All we know is it’s mouth-watering.

Signatures Restaurant: Signatures and theGrill at Signatures offer a wide variety of locally-sourced fare alongside stunning bluff views for lunch, happy hour, and dinner services. The vegetarian sandwich is good enough to convert any self-described carnivore out there. They had us at portabella mushrooms and brie cheese.

Beno’s Deli: This classic lunch joint is located in the heart of downtown in a historic building that used to be the Winona County Courthouse. Diners have been enjoying sandwich creations like the Ricky Ricardwich: Cuban pork, mustard, provolone cheese & coleslaw served on a ciabatta roll, for more than 30 years, and that description just told you why.

Heirloom Seasonal Bistro: One of Winona’s newest restaurants to open downtown changes their menu on the daily, but the recent delicacy dubbed the Smash Slider shows you everything you need to know—the burger is created using 100% local ingredients including melted red wine cheddar, bacon jam, roasted garlic aioli & arugula. Also, on a Bloedow Bakery roll. Of course.

Winona Sandwich Company: It’d be crazy of us not include this local favorite in our list. Now serving breakfast sandwiches—yum!—WSO also bakes all bread in-house, daily, and our lunchtime craving is the Spicy Turkey Melt with jalapenos and chipotle mayo.

No morning is a Winona morning without Bloedow Bakery donuts, but if you want a great omelet, (we recommend the Philly Cheesesteak!), to kick off your day, head to Anacabe’s Little Kitchen in the heart of Goodview, less than 1 mile out of Winona city limits on West 6th Street.

Stop at the breathtaking WNB Financial downtown to marvel at the Tiffany & Co. Stained Glass, marble, and surprising African Safari Exhibit on the third floor—a tribute to the bank’s founders who were hobbyist game hunters in the 1920s.

Don’t miss the historic Watkins Heritage Museum & Store. Free admission and filled with the company’s incredible 150-year-old story. Take home your own pepper, vanilla and cinnamon.

Enjoy lunch and a view at Signatures Restaurant in the bluffs, just a few miles from Highway 61. The property has dozens of signed memorabilia on the walls for you to check out as well—everything from a signed Elvis Presley yearbook, to a B.B. King guitar and more.

Please your college student by taking them to the Downtown Meat Market to load up on quality meat. Bluff Country Co-op, Hy-Vee and Midtown Foods are also staples for everyday grocery runs.

Drop your student back off at the dorms, or bring them along, and head to Prairie Island Campground where you can rent watercraft to explore the backwaters of the Mississippi River, with or without a guide.

Take advantage of the winter scenery in Winona and rent fat bikes or snowshoes from Adventure Cycle and Ski downtown, get recommendations on the best trails, and experience the beauty of the snowy bluffs. (Winter)

Dinner at Blooming Grounds Coffee House downtown is a relaxed affair, with small plates for sharing, artisan pizzas, draft and bottled beers and a great selection of wines.

Walk over to Winona’s brew pub and sip on a fresh craft beer at Two Fathoms Brewing. Depending on the night, you could participate in rowdy trivia, or kick back and listen to live music.

Not quite ready to retire to your bed for the evening? Stop by No Name Bar to enjoy a craft cocktail and additional live entertainment.

Winona’s legendary Bloedow Bakery, called one of the best in the country by Saveur Magazine, is a must-do on every foodie itinerary. The maple long john will make you weep with joy.

Blue Heron Coffeehouse is prized by locals for its innovative, made-from-scratch breakfast and lunch menus that offer vegetarian and vegan options among its mouthwatering array of frittatas, soups, sandwiches and more.

Lakeview Drive Inn is the perfect afternoon pit stop for a frosted mug of its secret-recipe root beer that has been pleasing palates since 1938.

For dinner, Nosh Scratch Kitchen offers epicurean fare, creative cocktails and a moody vibe, and nearby Heirloom Seasonal Bistro serves café-style farm-to-table freshness with an elevated flair that has people raving.

For a more international flavor, head to Norvary, a Vietnamese restaurant serving elegant, interesting dishes that consistently get 5-star reviews, or visit Miya Japanese Bistro for traditional Japanese cuisine that is artfully prepared. If the presentation isn’t enough to blow your socks off, the flavors definitely will. Sushi and hibachi dishes delight all palettes.

Sapori di Sicilia creates authentic Italian fare using ancient traditions from the region of Sicily thanks to its Sicilian-trained chef. The menu includes sumptuous house-made pastas and gelatos, daily baked goods, and Italian pastries to die for at this impeccable replica of an Italian cafe.

Muddled Thyme specializes in craft cocktails, gourmet brick-oven pizzas, and a swanky atmosphere in its beautiful downtown space, while Island City Brewing Company features local brews, live entertainment, and expansive indoor and outdoor seating along with a bookcase full of games to borrow.

Swing into The Lafayette for a next-level cocktail in a sumptuously elegant environment. The mixologists there take every meticulous step necessary to serve you the perfect libation in a beyond-perfect environment.

The cornerstone of any romantic weekend in Winona is a stay at the Alexander Mansion Bed & Breakfast, a spectacularly restored historic home that serves as a four-star bed and breakfast. Opulent décor and indulgent four-course breakfasts set the perfect tone for a romantic getaway.

Grab a picnic lunch from Bluff Country Co-op and find a spot in Lake Park to spread a blanket and soak in the day. After lunch, buy a day pass from Lake Lodge and try your hand at canoeing, kayaking, stand-up paddleboarding, or – the ultimate in romance – a bicycle built for two.

Treat yourselves to dinner at Signatures Restaurant, a fine dining establishment in what was once Winona’s historic country club on the outskirts of town. The clubhouse is now open to the public and serves gourmet and classic American fare along with incredibly good bottles of wine from the storied wine cellar.

Watch the sunset from atop the bluffs thanks to Garvin Heights Overlook - a city park that offers a sweeping view of the Mississippi River Valley. To sit a spell, hike down the footpath to the left of the overlook to a large, flat rock perched on the edge of the bluff, which offers a blissfully romantic spot to watch the world below go by.

Start your day downtown at Blooming Grounds Coffee House, Blue Heron Coffeehouse or Acoustic Café - where pieces created by local artists adorn the walls.

No trip to Winona is complete without a visit to the Minnesota Marine Art Museum, a stately building on the banks of the Mississippi River that houses an astonishingly global collection of artwork. Browse paintings from masters that belong to the permanent collection and contemplate the variety of traveling exhibitions that keep the museum fascinating and ever-changing.

The Great River Shakespeare Festival – a nationally cast event that runs from late June through July each year – boasts an array of different plays each season, and a weekday or weekend visit timed right could catch several of them. 

Visit in July to take in one of the world-class performances of the Minnesota Beethoven Festival – an annual event that brings in classical musicians from around the world.

A stroll through Winona’s downtown, where 13 blocks are on the National Historic Register thanks to beautifully preserved Victorian architecture, will fill you with wonder at the art of architecture, which includes incredible stained glass windows found in Merchants Bank and WNB Financial. 

Theatre du Mississippi and the Minnesota Conservatory for the Arts offer productions throughout the year, as does the Highway 61 Concert Series, which brings nationally touring musical performances to Winona.