Winona is a hidden gem of a small town for those looking to safely get out of the city for a weekend. With beautiful scenery, year-round outdoor activities, a charming downtown dining and shopping scene, and southeastern Minnesota’s best donut shop, Bloedow’s, there’s something for everyone. (I live in the Twin Cities now, but I grew up in Winona and still head back to visit family. This story is based upon a trip earlier this year.)
A peak trip to Winona starts with the drive. If you’re coming from Minneapolis or St. Paul, the fastest route is Highway 52 south through Rochester. For a more-scenic trip, I suggest taking either Highway 61 through Red Wing or crossing over to Highway 35 in Wisconsin. Both routes run along the Mississippi River and offer beautiful foliage, especially in the fall.
Day 1: Historic Check-In
As far as accommodations go, Winona’s most-inviting option is the Alexander Mansion Historic Bed and Breakfast, built in 1886 by Minnesota Supreme Court Chief Justice Thomas Wilson. Located in the center of town, the 10,000-square-foot mansion is just a short walk from shopping, dining, cafés, Lake Winona, and the Winona Levee. The Victorian-style B&B boasts a large private yard, a wrap-around screened porch, a cozy library and fireplace room, three dining rooms, a tea room, and luxurious private suites. Each room is so beautifully designed, you might spend all weekend just exploring the mansion. Booking includes a delectable four-course breakfast made with local, organic ingredients.
Today, the mansion is owned and operated by Richard Grabow, a wonderful host with a deep knowledge of both the B&B and the town. Grabow also offers structured activities, both throughout Winona and at the mansion, such as winter movie nights by the fireplace, wine socials, and tea times in the Mad Hatter-themed tea room. As for social distancing protocols, the B&B hosts only eight guests at a time, giving everyone optimal room to spread out. Guests are split between the three dining rooms for breakfast to ensure safety.
When you arrive in Winona, you might want to spend your first night unwinding with a nice dinner. The new Nosh Scratch Kitchen offers local farm-to-table dining, a rotating seasonal menu, and the best cocktails in town. The dining room is modern and romantic, dimly lit with dark wood walls and local artwork displayed throughout. Indoor tables are well spaced for social distancing, and same goes for the garden-style patio, lit by string lights. Nosh also offers spectacular takeout for picnic-style dining at Lake Winona or the Levee.
End your evening with a glass of wine at Blooming Grounds Café in the center of downtown. On Friday nights, the city closes off streets to accommodate safe outdoor dining. Blooming Grounds has a nice setup, a great wine and beer menu, and live music.
Day 2: Sights and Snacks
Start your Saturday by taking in some of Winona’s natural beauty. The Garvin Heights lookout offers an exquisite panoramic view of the entire town, including both lakes and the river, and morning is the best time to see it. If you’re up for a hike, you can follow the Garvin Heights hiking trail from the bottom of the bluff to the lookout. There’s a more rugged hiking trail once you get up to the lookout, and the scenery is beautiful. To admire the view with a cup of coffee, just drive up the hill, park, and walk to the lookout.
To refuel, head to Bloedow’s Bakery, which has been around since 1924. Every Saturday morning, you’ll find a line of eager faces all the way down the block, waiting to pick up their favorite baked goods. The pillowy maple long johns are a town favorite, and you can also add bacon to the thick slather of creamy maple frosting. My favorite is the glazed croissant, but they sell out quickly. Pro tip: Skip the line! Call ahead and pick up your order at the walk-up window.
Any Winona native will tell you Mugby Junction brews the best coffee in town, from drip to specialty drinks. My favorite is the perfectly spiced and extra creamy dirty chai latte. (In pre-COVID times, I would urge you soak up the natural light and admire the art-lined walls and tin ceiling.)
At the Winona Farmers Market, pick up a jar of local honey, homemade jam, maple syrup, or other goodies. Castlerock Sourdough is a must-stop stand for the jalapeño cheddar and cardamom raisin breads. The Pop Up Peddlers sell handmade, reusable beeswax wraps to replace plastic wrap and sandwich bags in your home. On your way out, pick up some authentic Indian cuisine from Infuzn to heat up and enjoy later.
Next, stop into a couple of Winona’s best museums. The most popular is the Minnesota Marine Art Museum, which rotates exhibits regularly. If you’re a foodie, you’ll love the Watkins Heritage Museum, which shares the history of Watkins seasonings and extracts. The Winona County History Center offers a deep look into the origins of Winona.
Wind down for the night with dinner from Miya Japanese Bistro, serving sushi and hibachi. Be sure to pick up an order of Gyoza, they’re delightful.
Day 3: Shop Local
Spend Sunday exploring Winona’s historic downtown, which features beautifully preserved brick buildings hosting a variety of locally owned businesses. A-Z Collectibles is my preferred place to get lost for hours. It’s an antique jungle littered with everything from vintage dolls and clothes to teacups and records. For something unique and handmade, stop into Jovy Rockey Jewelry. Rockey creates and sells her own beautiful pieces in the store and shares the space with other local creators to vend everything from home decor to body care.
Just across the street is The Loft on Third, a boutique specializing in high-quality trendy, but distinct, women’s clothing. I stopped in for a pair of jeans and spoke with owner Lynn Nelson, who recently moved to Winona from La Crescent. She expressed her love for the town and community but felt that it needed a shop that complemented local style. I believe Nelson captured her vision well.
Grab some lunch at the cozy Acoustic Cafe. The coffee is great, and the warm hoagies are mouthwatering. I always order the garlic hummus hoagie and a cup of chili. Dining in offers intimate booth seating or opt for takeout and enjoy your lunch by the Winona Levee.
This itinerary features all of my hometown favorites, but Winona hosts several events throughout the year such as Beethoven Festival, Frozen River Film Festival, and Handmade Neighborhood. Check out Visit Winona’s website for information on upcoming events, as well as other year-round and seasonal activities.