- Exploring the hidden gems of Western Wisconsin—curating unforgettable stays and sharing the places locals love most.
Maiden Rock is a village you could miss if you blinked: a few blocks of old storefronts tucked between the bluffs and the river, about 45 minutes south of Prescott on Highway 35. In summer, it’s a stop on the way somewhere else. In winter, it’s the destination.
The crowds are gone, the river road is quiet, the bluffs are dusted with snow, and eagles sit in the trees along the open water. This is the winter day I’d plan for you if you were staying with us in Prescott: a slow drive, a warm drink, a snowy walk to a 400-foot bluff, and a stop in Pepin for a Christmas market or a glass of wine under a heated portico.
Don’t think of the drive as the part before the fun. Highway 35 south of Prescott follows the Mississippi through Diamond Bluff, Hager City and Bay City, and then the bluffs close in as you reach Lake Pepin, the wide stretch of the river. In winter you can see the shape of the land in a way you can’t in summer: every ridge and coulee, every limestone face. Watch the trees along the open water for bald eagles. They gather wherever the river stays open, so keep a passenger on eagle duty.
Insider tip: Stop at Sunrise Coffee on 35 in Bay City for a Bomber (espresso, chocolate, peppermint and vanilla). Winter weekend hours are 8 a.m. to 2 p.m.
In the middle of the village, Maiden Rock Mercantile is a locally owned shop and coffee counter. They pour espresso with Peace Coffee beans and serve local baked goods, sandwiches and wraps, and the shelves are full of goods from local makers and food producers. It’s a good place to find a gift you won’t find anywhere else, and the kind of place where the person behind the counter will tell you what’s going on in town.
Insider tip: The Mercantile is closed Tuesdays and Wednesdays, and winter hours can shift. Check before you go.
Just outside town, Maiden Rock Bluff State Natural Area protects 263 acres around a limestone bluff that rises about 400 feet over the river and stretches nearly a mile. A 1.5-mile loop leads through prairie and oak woods to a string of clearings and an overlook at the edge of the cliff. In winter, with the river frozen at the edges and the Minnesota bluffs white across the water, the view is something else. The area is open for hiking and cross-country skiing.
The bluff is named for a legend about a young woman who leapt from the ledge rather than be forced into marriage, and it’s also one of the few natural bluffs in Wisconsin where peregrine falcons nest. In winter, look for bald eagles and, if you’re very lucky, a golden eagle riding the wind along the face.
Insider tip: The DNR doesn’t generally plow natural area parking lots, so after a big snow the lot may not be accessible. There’s no fence at the cliff edge, and it’s icy in winter. Wear boots with traction, stay well back from the edge, and skip it if conditions look rough. The view from the river road is beautiful, too.
Up on the bluff between Maiden Rock and Stockholm, Maiden Rock Winery and Cidery makes small-batch, gluten-free hard ciders (the Honeycrisp and Red Hawk are my picks) along with fruit wines, apple strudel and jams. Their schedule is seasonal, so call ahead before a winter visit. If they’re open, a jar of their jam is the perfect thing to bring home.
Ten minutes on, Stockholm Pie and General Store is open year-round and has been named the best pie shop in America by USA Today readers. On a cold day, I go savory first, with a chicken pot pie or a slice of the apple sausage quiche, and then sweet: the Kentucky Bourbon Chocolate Walnut or the Lingonberry Lemon. Order a whole pie ahead if you want to take one home.
Finish the day ten minutes farther south at Villa Bellezza in Pepin, a winery built like a little Italian village around a piazza with a fountain. In winter they heat the porticos and put fur throws on the chairs, so you can sit outside with a glass of wine and watch the snow. Inside, il Forno serves wood-fired pizza and pasta.
From November 14 through December 20, 2026, the piazza hosts their European Outdoor Christmas Market on Saturdays and Sundays from 11 to 5. It’s free, and it’s one of the most charming holiday outings on the river. More ideas in my guide to a winter day in Pepin.
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.
