The largest of Minnesota ’s river towns below St. Paul was founded as Montezuma in 1851 by Orrin Smith, captain of the steamboat Nominee, who needed a location between Galena and St. Paul to load fuel wood. Within two years it had grown into a town of 300 and was renamed Winona (“firstborn daughter” in the Dakota language).
Not only did steamboats resupply themselves here, but when the local land office opened, settlers heading west poured in to secure farms and purchase provisions for a new life on the prairie. By the end of the decade nearly a dozen sawmills were turning, and the town thrived.
Flour mills also went up in the 1850s, and the settlers who had previously passed through town continued to enrich it by shipping their harvest back from as far west as South Dakota, first by oxcart and then, in 1862, along the Winona and St. Peter Railroad.
Ironically, by the 1880s this treeless, barren plain had become one of Minnesota’s greatest lumber towns and the fourth-largest grain market in the country, reportedly producing more millionaires than any other similarly sized city in the nation.
By the late 19th century, cities to the west had appropriated much of the flour business, and around the turn of the 20th century the surrounding forests had largely been cleared. As the old industries died out new ones, such as brick-making, dairying, meatpacking, sauerkraut-making (at one time Winona produced more than any place west of Chicago), and quarrying, arose to keep the city prosperous.
Sugar Loaf Mountain, visible from across the city and well beyond, is a 500-foot-tall monument to the latter industry. The 85-foot pinnacle at the top appears natural, but is, in fact, the remains of an 1880s quarry. If you want to climb it, a well-worn trail leads up the south side of the peak from the redbrick building (West Burns Valley Rd.) serving the city’s water reservoirs. Today, despite a population of over 27,000, it is a fairly sleepy town most of the time.
The Amtrak (65 Mark St. E., 507/452-8612 or 800/872-7245, www.amtrak.com ) Empire Builder service arrives from St. Paul about 10 a.m., and the western service comes through at 7:50 p.m. A walk-up return ticket from St. Paul costs $20.
Go Carefree Shuttle (608/781-5181, www.gocarefreeshuttle.com , $45 one-way, reservations required) vans go to the Twin Cities  from the Quality Inn (956 Mankato Ave.), St. Mary’s University (400 Terrace Heights), Winona State University (264 Mark St. W.), and the Amtrak Station (65 Mark St. E.) five times a day.
Locally, Winona Transit (507/454-6666) has a limited bus service available weekdays until around 6 p.m. The city also has two cab companies: Economy Cab (507/454-7433) and Yellow Cab (507/452-3331). Hertz (275 W. 2nd St., 507/454-2888, www.hertz.com , 7 a.m.–5 p.m. daily) and Enterprise (1111 Service Rd. W., 507/454-4462, www.enterprise.com , 7:30 a.m.–5 p.m. Mon.–Sat., 9 a.m.–noon Sun.) are the national car rental agencies in town.
There is public dockage for short-term visitors on Front Street downtown. For overnighters there is the Winona Yacht Club (24 Laird St., 507/454-5590) near downtown and Dick’s Marine (507/452-3809) over on Latsch Island—both are full-service facilities.