- Exploring the hidden gems of Western Wisconsin—curating unforgettable stays and sharing the places locals love most.
There’s one week every October when the bluffs above Prescott seem to change color overnight. You go to bed with green hills and wake up to gold, rust and red stacked all the way up the river valley. The air gets that crisp, apple-cider edge to it, the orchards are heavy with fruit, and every bend in the Great River Road looks like a postcard someone forgot to mail.
Prescott is only about 40 minutes from St. Paul, which means you can leave work Friday afternoon and be sitting on the river with a glass of sangria before dark. If you called me and said, “We want one perfect fall weekend, plan it for us,” this is exactly what I’d tell you.
Check-in is at 4 p.m. Drop your bags, pull on a sweater and walk to dinner. Everything downtown is just a few minutes away on foot, so the car can stay parked until morning.
On a cool fall night, I’d send you to Muddy Waters, right on the St. Croix. If the deck’s too chilly, grab two seats at the bar inside. The stools are comfortable, the bartenders are great, you get the full menu and you’ll end up chatting with the regulars. Start with Leon’s house-smoked salmon, then order the house-smoked prime rib (Fridays and Saturdays only) with a side of au gratin potatoes. The house red sangria is the right way to kick off the weekend. They don’t take reservations, so don’t overthink it.
Start at Twisted Oak Coffee House on Broad Street. Order the Paul Bunyan, a latte made with organic maple syrup, and The General, a ham, egg, cheddar and sriracha sandwich on an everything bagel, to go. Then head south on Highway 35, with the Mississippi on one side and the bluffs on fire on the other.
About 35 minutes down the river, stretch your legs at Maiden Rock Bluff State Natural Area. From the little parking lot up on the bluff, the trail runs about a mile out and back through oak savanna and prairie, past red cedars that have clung to the rock for 250 years, to a limestone ledge about 400 feet above the river. In October, the whole valley below you is ablaze. Keep an eye out for peregrine falcons. This is one of only a handful of cliffs in Wisconsin where they nest on natural rock.
The bluff is named for an old Dakota legend about a young woman named Winona, who leapt from this cliff rather than marry a man she didn’t love. Standing up there, you’ll understand why the story has lasted more than 200 years.
A few minutes south, the village of Stockholm has fewer than a hundred residents and one of the most famous pie shops in America. Stockholm Pie & General Store was voted #1 in the country by USA Today readers, and from October through December, they bake pumpkin, pumpkin cream cheese and pumpkin pecan pies. Split a chicken pot pie for lunch, then a slice of Montmorency cherry for dessert. If you’re feeling silly, get the pie shake.
Walk it off along Spring Street, where the tiny downtown is packed with galleries and shops like Scandihoo, Indigo Swan and Great River Press.
Just outside Stockholm, Maiden Rock Cidery, Winery & Orchard sits on a hilltop farm where Herdie Baisden and Carol Wiersma grow around 50 kinds of apples. Do a cider tasting, then take your glass out to the gazebo and look out over the orchard. Take a bottle back for later. Hours change with the season, so call ahead.
Finish the day 10 minutes further down the river in Pepin, at Harbor View Cafe. It’s been serving dinner by the marina since 1980, and it’s one of those places people drive hours for. There’s no printed menu. Everything is written on the same chalkboard the original owners used, and it changes with what the local farms and the garden out back have that day. Shelves of books line the walls.
Ask your server what’s good tonight, and if the pan-fried halibut with black butter caper sauce is on the board, order it. Whatever you get, save room for the chocolate buttercream pie. It’s such a tradition that new staff members get a slice on their first day.
Good to know: Harbor View doesn’t take reservations, so arrive early and browse Pepin’s shops while you wait. Fall hours are Thursday 3 to 7 p.m., Friday 3 to 8 p.m., Saturday noon to 8 p.m. and Sunday noon to 7 p.m. It closes for the season before Thanksgiving and reopens in March.
Then drive back to Prescott along the dark river, full and happy.
Sleep in, then walk to The Kitchen Table on Broad Street. Order the Lobster & Asparagus Benny, the dish that got this little breakfast spot featured on America’s Best Restaurants, or the Hangover Hash if you need it. Add a Bloody flight if you’re feeling festive. It’s walk-in only, so the earlier you go, the shorter the wait.
On your way out of town, stop at Young Acres, just south of Prescott on Highway 35. This family farm has 17 varieties of apples, and in mid-October you’ll find Honeygold and Fireside on the trees. Pick a bag, then warm up with hot cider in the country store. Sunday hours start at noon.
Before you head home, drive up to Freedom Park on the bluff above town. From the overlook at the Great River Road Visitor and Learning Center, you can watch the clear St. Croix and the muddy Mississippi run side by side, framed in fall color. It’s the perfect way to say goodbye until next time.
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.
