- Exploring the hidden gems of Western Wisconsin—curating unforgettable stays and sharing the places locals love most.
The first time I drove to Pepin in the dead of winter, I almost turned around. It was gray and cold, the radio said more snow was coming, and I figured everything would be closed. Then the road came around the bend below Maiden Rock, the whole Mississippi valley opened up white and silver in front of me, and three bald eagles lifted off a tree right beside the car. I pulled over, sat there with my coffee going cold and thought, why doesn’t anybody come down here this time of year?
That’s the secret about Pepin in winter. The summer crowds are long gone, and what’s left is a quiet village on the river, a winery that looks like it was lifted out of the Italian hills, and the snowy clearing where the author of the Little House books was born. It’s about an hour south of Prescott on Wisconsin’s Great River Road, and it makes for one of the best winter days I know.
Here’s exactly how I’d plan it if you called me and said, “We want to get out of town for a day. Where should we go?”
Pour the coffee into travel mugs and head south out of Prescott on Highway 35. For most of the hour, the road traces the Mississippi, with limestone bluffs on one side and the wide, frozen-edged river on the other. You’ll pass through Bay City and Maiden Rock, two tiny river towns that look like they’ve been sitting exactly where they are for a hundred years.
As you come into Maiden Rock, look up at the bluff above town. It rises about 400 feet over the river and runs for nearly a mile. The name comes from an old Dakota legend about a young woman named Winona who, rather than marry a man she didn’t love, leapt from the cliff. Explorers were writing the story down as early as 1805, and it still gives me a little chill every time I drive under that rock.
Winter is when the bald eagles come to this stretch of the river. They gather wherever the water stays open, and it’s not unusual to count a half dozen in the bare trees along the road. Early morning and late afternoon are best. Bring binoculars, take your time and only pull over where there’s a safe spot to do it. Nobody’s behind you anyway.
If you fall in love with the eagles (and you will), keep going past Pepin to Nelson and cross the river to the National Eagle Center in Wabasha, Minnesota. They have rescued eagles you can see up close and a live eagle program every day at 1 p.m.
Ten minutes before Pepin, you’ll roll into Stockholm, a village of fewer than a hundred people that happens to be home to one of the most famous pie shops in the country. Stockholm Pie & General Store was voted the #1 pie shop in America by USA Today readers, and Food & Wine has called it one of the country’s most iconic pie shops. It lives up to every word.
The crust is the secret. The recipe traces back to a friend of the family in rural Kansas, and it’s flaky in a way that makes you slow down. The Montmorency cherry is the slice people drive for. In winter, look for the seasonal pumpkin pecan and, from November through December, the eggnog custard. If you need something savory to justify dessert, the chicken pot pie or the Swedish hand pie (beef, potato and cheese) is a meal on its own.
Here’s my tip: order the pie shake. Yes, it’s pie in a milkshake. It’s ridiculous, and you should absolutely do it.
Before you leave, wander through the general store side. It’s three connected storefronts full of Wisconsin cheese, local wine, private-label jams, vintage candy and old-fashioned toys, with a little reading nook tucked in the corner. Pick up a whole pie for later, too. Just know they’re closed on Tuesdays and Wednesdays.
Pull into Villa Bellezza at the edge of Pepin and you’ll feel like you took a wrong turn somewhere around Rome. Owners Derick and Julie Dahlen built it after years of trips to Italy and a friendship with a family in the little town of Zagarolo, outside Rome. The whole place is laid out like a small Italian village around the Piazza Bellezza, with a fountain in the center and covered porticos on three sides.
In winter, they heat the porticos and put fur covers on the chairs, so you can sit outside with a glass of wine while the snow falls on the piazza. It’s one of the most romantic spots I know in the whole region.
On Saturdays and Sundays from 10 a.m. to 2 p.m., Villa Bellezza serves a brunch buffet: egg strata, penne al forno, sausage and peppers, rosemary potatoes, fruit and, if you save room, biscotti and cannoli. The rest of the day, you order at the counter in Il Forno, the kitchen, and they bring it to your table. Get a wood-fired pizza to share (the spicy Italian with pepperoni, sausage and pancetta is my pick), and a bowl of the penne al forno, which never leaves the menu.
The chef behind it all is Antonio Cecconi, who learned to cook in his mother’s kitchen in Sardinia and wrote the Betty Crocker Italian Cookbook. If you’d like to make a weekend of it, sign up for one of his hands-on classes at La Scuola, the cooking school. This December, the lineup includes a Festa Italiana four-course holiday meal on December 12.
Villa Bellezza grows cold-hardy grapes on its own vineyards, and some of the wines have won serious awards. Their St. Pepin white took Platinum and “Best White Hybrid” at the Winemaker Challenge. Do a tasting, ask what’s new and take a bottle of something red home for the evening.
If you’re visiting before Christmas, plan your day around the Outdoor Christmas Market. It runs every Saturday and Sunday from 11 a.m. to 5 p.m., November 14 through December 20, 2026. The piazza fills with outdoor stalls, more crafters set up inside the Great Hall, and there’s mulled wine, pastries and pizza to keep you warm while you shop. It’s the most beautiful holiday shopping you’ll do all year.
Two more dates for your calendar: the Tree Lighting on November 13 at 6 p.m., and the release of their Pepin Nouveau wine on November 19, timed to the same day France and Italy open their young wines each fall.
About seven miles northwest of the village, on County Road CC, a small log cabin sits in a clearing in the woods. It’s a replica of the cabin where Laura Ingalls Wilder was born on February 7, 1867, built on the very spot she wrote about in the opening pages of Little House in the Big Woods.
In winter, with snow on the roof and the trees bare around it, it looks exactly like the illustrations you remember from the book. It’s a quiet stop. Read the signs, take a photo, stand there for a minute and let it sink in. Whether you grew up on the books or the TV show, it gets you.
One honest note: the cabin’s driveway isn’t plowed in winter, so this is a fair-weather stop. On a clear day after the roads are cleared, it’s worth the detour. After a fresh snowfall, save it for your next trip. The Laura Ingalls Wilder Museum in the village reopens for the season on May 1, so Wilder fans have a good excuse to come back in spring.
Head north on Highway 35 the way you came. The light on the bluffs changes as the afternoon fades, and the river turns pink and gold before it goes dark. By the time you’re back in Prescott, you’ll be ready for a warm dinner downtown and an early night.
Make downtown Prescott your home base and book direct with us: The Port of Prescott for boutique king suites steps from the river, Port After Dark for romantic suites made for couples, The Harbor Hotel for themed rooms and extended stays, and The Cove Guest House for downtown condos and group getaways.
