Just because the weather is getting colder doesn’t mean the wild adventures have to end. In fact, fall is the best time to see the Driftless Area in all its jaw-dropping glory. Peep the changing of the leaves from over 500 feet above the Mighty Mississippi and explore our historic downtown for some unique boutique finds. Whatever gets your wild side going, you’re sure to find it this fall in Winona, MN.
Scroll through the gallery below to find ideas for the perfect itinerary in Winona.
1. Bloedow Bakery
Photo Courtesy of Visit Winona; Kickstart your fall adventure with a world-famous donut from Bloedow Bakery. A Winona staple since 1924, Bloedow Bakery delights with drool-worthy donuts—including the legendary maple long john—bread, and sweets that will make your eyes roll back in bliss.
2. Garvin Heights Overlook
Photo Courtesy of Visit Winona; With your sweet tooth satisfied, hike the 378 steps at Garvin Heights Park. At the top, catch your breath and marvel at the spectacular view below of Winona, the surrounding bluffs, and the trees showing off their glorious fall colors. It’s a workout with one unforgettable reward.
3. Watkins Museum & General Store
Photo Courtesy of Visit Winona; After taking in the fall foliage, head to Watkins General Store & Museum in downtown Winona. Step back in time while browsing the company’s more than 150-year history, then stock up on spices and extracts for holiday baking, pick gifts for loved ones, and taste an iconic piece of Winona history.
4. Yarnology
Photo Courtesy of Visit Winona; Roll over to Yarnology to restock your knitting supplies and browse knitted, one-of-a-kind finds that will keep you cozy throughout the colder months. This is a great spot to get a jump on your holiday shopping for the knitter in your life or discover a new hygge hobby.
5. Winona County History Center
Photo Courtesy of Visit Winona; As you wander through downtown, step inside the Winona County History Center to discover the stories that shaped this river town. Explore exhibits and galleries and get a deeper look at Winona’s people, places and wild history. Don’t miss the newly opened River Gallery, complete with a nod to Winona’s boathouse community.
6. Old Tiger
Photo Courtesy of Visit Winona; Keep the nostalgia going at The Old Tiger, one of the city’s newest restaurants, housed in the beautifully preserved 1882 Winona & St. Peter Railroad Company Freight House. Enjoy classic American fare with a fresh, locally sourced twist, plus oysters and handcrafted cocktails overlooking the Mississippi River.
7. Hotel 44° North
Photo Courtesy of Visit Winona; After exploring Winona’s fall beauty, settle in at Hotel 44° North, just steps from the Winona Freight Collective in downtown. Unwind in the pool, soak in the hot tub or enjoy a session in the sauna. Sip prosecco on tap with Mississippi River views and wake up to a complimentary hot breakfast.

VisitWinona.com
924 Huff Street Winona, MN 55987
(507) 452-2278




