Winona

Winona, Minnesota, is a city sculpted by the mighty Mississippi River and framed by towering limestone bluffs, a striking landscape in the heart of the Driftless Area—a region famously untouched by ancient glaciers. This unique geography has created a visually captivating environment, where the river flows west to east and dramatic bluffs rise 500-600 feet, offering expansive views unlike anywhere else in Minnesota. The city itself lies on a sandbar of the Mississippi, surrounded by river bottoms and wooded bluff lands.

Beyond its natural splendor, Winona presents a rich array of history and culture. Once the ancient homeland of the Dakota Nation, led by generations of Chiefs Wapasha, the area’s Indigenous roots run deep. Later, European immigrants settled the area in 1851, transforming it into a bustling river town fueled by trade, particularly in wheat and lumber, and by the constant flow of steamboats. This era of prosperity is reflected in Winona's exquisite architecture, with grand buildings and elaborate cornices lining downtown streets, many of which are listed on the National Register of Historic Districts.

From Dakota Homeland to Lumber Boomtown

The Winona region's history stretches back millennia, with archaeological evidence indicating human habitation in the valley as early as 9500 B.C., and a Woodland period site dating from 800 B.C.-900 A.D. For centuries, it was the cherished homeland of the Dakota Nation, specifically the Mdewakanton band of the eastern Sioux, led by the Wapasha dynasty. The Dakota people, whose village of Keoxa was located at the site of present-day Winona, valued this area for its blufftop views, abundant wildlife, and access to the Mississippi River. The city's name, 'Winona,' derives from the Dakota word 'Winuŋna,' meaning 'first-born who is a daughter.'

European-American settlement began in 1851, following the Treaty of Mendota and the forced removal of the Dakota people to a reservation in western Minnesota. New arrivals, many from New England, were drawn by opportunities along the Mississippi. By 1856, Winona had rapidly grown into a bustling river town, with over 1,300 steamboats stopping annually. German immigrants also arrived in 1856, contributing to the city's growth. Winona quickly became a significant hub for wheat and lumber, even ranking among Minnesota's largest cities within a few decades.

The late 19th and early 20th centuries saw significant industrial development and the growth of Winona's port. This era of prosperity left a lasting architectural legacy. Charles G. Maybury, a prominent architect from 1865 to 1905, designed many of Winona's churches, schools, courthouses, and commercial buildings in various styles, including Italianate, Queen Anne, Richardsonian Romanesque, and Gothic Revival. Notable examples include the Basilica of St. Stanislaus Kostka, designed in a Polish Cathedral style, and the Winona County Courthouse, a highpoint of Richardsonian Romanesque architecture in Minnesota. The downtown area features Minnesota's largest collection of Victorian commercial architecture on the Mississippi, with many buildings in the Italianate or Queen Anne styles. Architects like George W. Maher also left their mark, designing the J.R. Watkins administration building and the Egyptian Revival Winona Savings Bank, which features Tiffany glass and fixtures.

Winona offers a blend of natural beauty and architectural grandeur. Begin with the iconic Sugar Loaf Bluff, a distinctive rock pinnacle offering scenic views and hiking opportunities. For panoramic vistas of the city and the Mississippi River Valley, head to Garvin Heights Park overlook. Explore the unique boathouse community along the Mississippi riverfront, a colorful tradition unlike anywhere else in the Midwest.

Downtown Winona is a treasure trove of historic architecture. Take a self-guided Stained Glass Trail tour to witness the city's remarkable collection of antique stained-glass windows, earning it the title of 'Stained Glass Capital of the U.S.' Wander through the Winona Downtown Commercial Historic District, which displays Minnesota's largest collection of Victorian commercial architecture on the Mississippi. Do not miss the Winona Savings Bank with its Egyptian Revival design and Tiffany glass, or the impressive Merchants National Bank in the Prairie School style.

For a deeper dive into local history, visit the Winona County History Center and the Watkins Heritage Museum & Store, which tells the story of J.R. Watkins, inventor of the 'money-back guarantee.' The Minnesota Marine Art Museum houses world-class art, including works by Picasso and Van Gogh, alongside marine-themed exhibits. For a unique historical experience, the Bunnell House offers live theatrical performances that transport visitors back to the 1850s. Outdoor enthusiasts can enjoy paddling the backwaters of the Mississippi River, hiking trails behind Holzinger Lodge, or exploring the multi-use trail at Levee Park.

Winona is beautiful year-round, but for comfortable weather and outdoor activities, the best time to visit is from mid-June to early September. July and September generally offer the most optimal weather conditions. Fall is particularly striking, with bursts of orange, red, and yellow foliage on the bluffs, especially from the third week in September to the second week in October. Summers are warm and wet, while winters are freezing, snowy, and windy, with January being the coldest month.

Winona is accessible by car, with scenic drives along Highway 61. Amtrak offers daily train service to Winona's historic station, connecting to St. Paul, Milwaukee, and Chicago, with free overnight parking available. Jefferson Bus Lines also provides routes from Winona State University to regional destinations, including the St. Paul-Minneapolis Airport.

Within Winona, public transportation is available through the Winona Transit Bus Service, operating Monday through Saturday with routes covering Winona and Goodview. Single rides are $2 cash, with options for route deviations and Dial-a-Ride service. The buses are wheelchair accessible and equipped with bike racks. Lyft rideshare service, Bird e-scooters (seasonally), and bicycle rentals are also available.

Parking in downtown Winona includes public parking lots and on-street parking. Be aware of alternate side parking regulations in effect from November 15 to March 15; vehicles must be parked on the even-numbered side of the street on even dates and the odd-numbered side on odd dates between 12:01 AM and 6:30 AM. Vehicles cannot be parked on city streets or public lots for longer than 20 consecutive hours.