For a moment, waves of upturned faces shimmer white, then glow pale pink, catching the changing hues of December fireworks. About 12,000 people, clustered shoulder-to-shoulder on a three-block stretch of downtown Red Wing, Minnesota, watch as the sky seems to burst with Christmas joy. Reds. Greens. Sparkling silver. The colors reflect in the Mississippi River like floating jewels.
It’s a fitting nightcap to the Red Wing Holiday Stroll and the generally festive spirit here, where discoveries both exciting and subtle unwind along a meandering 60-mile stretch of winter river and snow-dusted bluffs from Red Wing (55 miles southeast of Minneapolis) to Winona at the southeastern tip of the state. Along the Wisconsin side, tiny towns like Stockholm and Maiden Rock wedge between the frozen river and the towering bluffs, the clapboard shop exteriors lit like welcoming beacons amid foliage-stripped trees. All together, the route provides more than 100 miles of holiday exploration.
In the two-street village of Stockholm, you can almost hear the windows rattle when a freight train horn rumbles through the cold air. On the corner of the town’s only intersection, Janet Garretson prepares holiday pies amid a snowy swirl of flour and the lush scent of fruit. Plenty of new riffs on pie, such as eggnog custard and chocolate-peppermint cream, await within the canary yellow walls of the Stockholm Pie Company. But you’ll always find tradition at the core.
“I still use my grandmother’s pumpkin pie recipe,” she says. “My grandparents were honey producers, so we always put a little honey in our pumpkin pie.”
Honoring Stockholm’s Scandinavian heritage, Andrea Myklebust spins wool from her flock of Icelandic and Shetland sheep at rural Black Cat Farmstead. During the weekend of the 100 Miles event, families come to meet the sheep and buy her yarn displayed in the 19th-century farmhouse. “This is a really creative part of the world,” she says in her stove-heated studio, boasting of local artisans, bakers and innkeepers. She stops spinning, letting the bleating of sheep sift through her frosty window.
The weekend before, silent nights are in short supply during the Red Wing Holiday Stroll (held the Friday after Thanksgiving each year). Chestnuts roast in fire pits. A gaggle of local carolers belts familiar tunes, their voices competing with sleigh bell jingles coming from reindeer and horses pulling guests on sleighs and wagons. Strings of white lights turn downtown’s brick storefronts into a glowing pathway for the evening’s lighted parade. The crowd erupts as Santa waves from the top of a fire truck.
After the parade, a few groups stop by Red Wing Brewery, where longtime buds Scott Kolby and William “Norm” Norman serve homemade pizza on local Hanisch Bakery crust—a dash of brewing grains adds malty flavor—in the town’s first brewery since 1951. “We never imagined doing anything like this,” Scott says. “The more we delved into the history of Red Wing and its ability to support five breweries in the 1860s, the more excited it made us to revive the tradition.”
Downriver in Winona, during the 100 Miles of Christmas, gray-haired audience members who used to huddle around the radio with family smile as they hear familiar 1930s-era commercials for Pabst Blue Ribbon and Wheaties. “I remember that one,” someone whispers excitedly during the old-fashioned radio drama in downtown’s carpet-worn Masonic Theatre. Organ music swells, and one of the actors reads a letter from Santa to the town citizens. “Tranquility. You can feel it in the stunning bluffs that surround you and shield this place from the noise and busyness of the rest of the world.”
Under a canopy of stars, the rumbling motor of Trester Trolley briefly disturbs the tranquility. Riders sing along to holiday tunes as driver Clarence zigzags the Christmas-light-adorned trolley through Winona’s festively decorated neighborhoods. Like the 120-mile journey itself, the light tour changes a little each year, with a new burst of holiday color around every corner.
This journey starts in Fountain City on the Wisconsin side of the Mississippi River then heads 60 miles northwest to Hager City before crossing the bridge into Red Wing, Minnesota. From there, it’s 60 miles southeast on US-61 to Winona. Shop and restaurant hours may vary over the holidays; call ahead to check.
Gail Pommerening’s intricate pastels color the walls at Art and Soul in Alma. art-soul.org
Catch bird’s-eye views of Alma and the Mississippi River at Buena Vista Park before heading to Pier 4 Cafe and Smokehouse for tangy barbecue ribs. pier4cafe.com
It’s a 20-minute jaunt to Pepin, where Villa Bellezza winery’s Mediterranean-style complex stands out among small shops. The drier reds offer rich bouquets. villabellezza.com
Indulge in a large slice of Janet Garretson’s pie at Stockholm Pie Company. stockholmpieandgeneralstore.com
On top of the bluffs, Andrea Myklebust spins her sheep’s wool to create colorful yarns at Black Cat Farmstead. blackcatfarmstead.com
Across the river, five spacious guest rooms include whirlpool tubs at Round Barn Farm Bed and Breakfast outside of Red Wing. roundbarnfarm.com
The scent of oven-fresh bread fills tiny Smiling Pelican Bakeshop in blink-and-you’ll-miss-it Maiden Rock, Wisconsin (715) 448-3807. Next door at Cultural Cloth, longtime friends Jody Slocum and Mary Anne Wise sell textiles and other handcrafted items made by women in 17 countries throughout the developing world. culturalcloth.com.
You’ll see equally intricate handiwork at the new Pottery Museum of Red Wing across the river. The collection features more than 5,000 pieces of collectible ceramics. potterymuseumredwing.org
While in Red Wing, pair a malty pizza (the crust contains brewing grains) with the balanced Work Boot Red beer at Red Wing Brewery (redwingbrewing.com), then take a photo of the world’s largest boot—a size 638.5—inside Red Wing Shoe Store and Museum (redwing.redwingshoestore.com). (If you are in town during the Red Wing Holiday Stroll, enjoy reindeer-pulled sleigh rides, a lighted parade and fireworks at downtown’s annual holiday stroll.)
Condominiums at Willows on the River in Lake City come with fully furnished kitchens and spectacular views of Lake Pepin. willowsontheriver.com.
Kids love Lark Toys in Kellogg, but anyone can take a $2 spin on the hand-carved carousel. larktoys.com
Cute window displays at stores like Heart’s Desire lure shoppers to downtown Winona.
Take in landscapes by Monet and Van Gogh at the Minnesota Marine Art Museum (mmam.org) before snaking your way up Garvin Heights Road for sweeping city views at Garvin Heights Overlook and Park.
If you can stay for the evening, Signatures provides fine dining on regionally sourced entrees, such as pheasant and duck. signatureswinona.com Trester Trolley Christmas Light Tour shows off decorated homes. trestertrolley.com