The Twin Cities are a delightful place to celebrate the holiday season in, but sometimes we metropolitans pine for something a little more homey. For that, we need only drive a couple of hours southeast to the quaint town of Winona.

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Winona was settled by Yankees in 1851. The town has managed to preserve much of its original Victorian architecture, and indeed an entire 13 of its downtown blocks are on the National Register of Historic Places. When speckled by snow Winona becomes an especially whimsical place to celebrate the season in, very Dickensian yet unadulterated by ghastly workhouses or old women wearing yellowing, flammable wedding dresses.

Winona jokingly bills itself as “The Miami of Minnesota” because it’s so (relatively) warm there. A stretch of unfrozen Mississippi curls around it well into the wintertime, over which eagles may be spotted soaring in search of things that are good for eagles. Where you most want to walk in Winona this time of year is 3rd Street, because all of the merchants there deck out their windows and storefronts in full holiday regalia. What pastime is more Christmassy than looking at festive displays through store windows?

Winona’s main drag isn’t populated by run-of-the-mill stores. Their downtown has recently enjoyed a revitalization of sorts, and is now replete with lovely boutiques where you can find singular items to give as gifts (or keep for yourself). Pop into Urban Shoetique for gorgeous high-end designer footwear, see the treasures on display at Jovy Rockey Jewelry, or explore Pieces of the Past for goods from local Midwestern artisans that you simply couldn’t find anywhere else. The area around 3rd Street is also an embarrassment of riches when it comes to restaurants, which is good because shopping is second only to running the Iditarod in terms of the amount of exertion required. And if you can, be certain to visit one of the Winona Artisan Markets, weekend pop-up events where artists from throughout the area set up to sell their original pieces.

Winona becomes a town of music during the holidays. Throughout the place you can take in every sort of performance you could fathom, including The Nutcracker at Saint Mary’s University’s Page Theater, the medieval choir Blue Heron Consort at one of the town’s several historic churches, and the Highway 61 Concert Series at a quaint local theater. But perhaps nowhere in Winona is quite as well suited for your listening pleasure as Levee Park, where Live @ the Levee concerts are held by fire pits, a complimentary ice skating rink, and Winona’s Winter Holiday Market.

It’s quite the pretty scene, Christmas music resonating over the Mississippi as families glide around the ice rink. They’re moments like that which make Winona the perfect little day trip this time of year, and even the drive there is going to delight with its gorgeous riverside scenery. To learn more about what the Victorian refuge holds in store, please visit


By David Scheller