- Exploring the hidden gems of Western Wisconsin—curating unforgettable stays and sharing the places locals love most.
Every couple has the same conversation sooner or later. “We need a weekend away.” Then someone pulls up the map, and the options all start to look the same: two and a half hours to Duluth, two and a half to La Crosse, half of Saturday gone before you’ve even checked in.
Here’s the thing nobody tells you: the weekend you’re looking for might be 40 minutes from St. Paul. Leave work at four on Friday, and by the time the sun drops you can be sitting on a deck where the St. Croix meets the Mississippi with a drink in your hand, wondering why you didn’t do this sooner.
This is how I’d spend 48 hours in Prescott and along Wisconsin’s Great River Road if I were planning it for the two of you.
Save this one for your next free weekend.
Prescott is small enough that once you park, you’re done driving for the night. Everything that matters, the restaurants, the river, and the marinas, is a few blocks from Broad Street. Where we’d stay: The Port of Prescott, where every suite has a king bed and a fireplace, or one of the three Port After Dark suites across the street if this weekend is all about the two of you.
For the first night, I’d send you to Muddy Waters. It has three levels of deck right on the St. Croix, blues on the speakers, and a menu that’s better than it needs to be. Start with Leon’s house-smoked salmon, and on Fridays and Saturdays, the house-smoked prime rib is the move. Get the au gratin potatoes on the side. Here’s a local tip: if the deck is full, grab two seats at the bar. That’s where you’ll end up talking with locals, and that’s half the fun. They don’t take reservations, so don’t overthink it.
After dinner, walk it off. Head up to Freedom Park and the Great River Road Visitor and Learning Center, perched on the bluff above town, where you can see the clear water of the St. Croix meet the muddy Mississippi. Then wander back down along the water and watch the boats come in for the night.
Saturday is the reason to come. Head south from Prescott on Highway 35, and within half an hour the road starts doing something special: it hugs the river, climbs past limestone bluffs, and opens up to views where the Mississippi widens into Lake Pepin. Pull up the route on Google Maps, but don’t rush it. The whole point is to pull over.
Maiden Rock Bluff State Natural Area is the payoff of the whole drive. A short hike takes you out to the edge of a bluff with a sweeping view over the river valley. Bring a light jacket, because it’s breezy up there, and give yourselves time to just stand and look.
Stockholm has about 65 residents and more art galleries than seems possible for a town that size. It’s also home to Stockholm Pie & General Store, a nationally awarded pie shop that also does a real lunch of soups and sandwiches. Order the double lemon, and take a whole pie home for later. You won’t regret it. Then spend an hour wandering the galleries and shops.
Keep going to Pepin, where Villa Bellezza looks like it was lifted out of the Italian countryside, with a stone piazza and a glass of wine waiting. Or stop at Maiden Rock Winery & Cidery for hard cider made from apples grown right there. For more options along the way, see our Wineries & Wine Tastings guide.
On your way back north, stop in Bay City, 15 minutes south of Prescott, for dinner at Chef Shack. It’s a 40-seat room in a 1920 building with a vintage bar, run by chefs who earned a James Beard semifinalist nod. The menu is short, seasonal, and changes constantly, and the honeycomb ice cream is the dessert people talk about all the way home. It’s open for dinner on Friday and Saturday, and reservations are a must.
Prefer to stay south? The Harbor View Cafe in Pepin has been cooking from scratch across from the harbor since 1980, and people drive from the Twin Cities just for dinner. It’s open limited days and closes for the season in late November, so check before you go. You’ll find both in our Romantic Restaurants guide.
Sleep in, then walk to The Kitchen Table on Broad Street. The walls are covered in a few hundred cheeky signs, the staff is quick with a joke, and the Lobster & Asparagus Benny got the place featured on America’s Best Restaurants. If you’re feeling festive, order the Bloody Mary flight. It’s walk-in only, so go earlier if you’d rather skip the wait.
Browse the shops along Broad Street, grab a coffee for the road, and take one more look at the river. You’ll still be home by early afternoon, with plenty of Sunday left.
The best weekends don’t need a long drive, a flight, or a packed itinerary. They need a river, a good meal, and nowhere else to be. We’ll leave the light on. đź’™
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.
Celebrating something special? Our guide to romantic getaways in Wisconsin maps out date stops all along the river road.
