- Exploring the hidden gems of Western Wisconsin—curating unforgettable stays and sharing the places locals love most.
Okay, so next time you come to Prescott, we’re eating outside. No debate. This town sits right where the St. Croix meets the Mississippi, and nearly every good table on Broad Street has either a river view, a sidewalk full of people-watching, or a freight train rumbling across the bridge while you eat. Sometimes all three.
Here’s where I’m taking you, and exactly what we’re ordering.
If you only have one evening, we’re going to Two Rivers. It’s got that rustic lodge meets sports bar vibe, but the real star is the patio. It’s multi-level, it has its own full outdoor bar, and it looks straight out over both rivers. Every time a train crosses the bridge, the whole patio stops to watch. It never gets old.
We’re starting with a round from the outdoor bar. The Two Rivers Signature Bloody comes loaded with a beef stick and a spicy pickle, but if it’s hot out, I’m getting the DragonBerry Mojito or a Coconut Lavender Margarita. And if you’re not drinking, just ask. They’ll turn any cocktail into a mocktail.
Food-wise, we’re splitting the Ellsworth cheese curds. They batter them in-house, and they’re the real deal. After that, you’ve got choices. The walleye dinner is honestly one of the best values in town. My friends who come here all the time swear by the Cranberry Turkey Brie Sandwich, and one of them told me skipping it is basically a sin. On a cold night, Mom’s Pot Roast is pure comfort.
And now my favorite part, because I’m a dessert girl. Two Rivers does a seasonal menu, and there’s almost always a seasonal dessert on it. This summer it was a Salted Caramel Ice Cream Sandwich. The Cookie Butter Pie is always a winner, and if you’re feeling brave, the Paul Bunyan Carrot Cake weighs a full pound. Bring a friend. Or two.
Insider tips:
For lunch, we’re grabbing a table at the Roadhouse’s sidewalk cafe on Broad Street. It’s the perfect spot to watch downtown go by. This is a true mom-and-pop place, and the owner does the cooking himself. Friends who stop in always tell me the same thing: this is not bar food.
I’m ordering the Everything But the Kitchen Sink Melt, like always. But you need to try the cheeseburger wontons. It’s a whole burger, pickles and all, tucked into crispy wontons with a tangy burger sauce. It sounds weird. It’s amazing. The brisket and ribs come off the smoker, and the shrimp and grits and street tacos are big hits too.
And here’s the surprise: the Roadhouse makes sushi, and it’s easily what people talk about most. Order the Roadhouse Roll, their best seller. It’s served Wednesday through Sunday, and it sells out fast on weekends, so don’t wait until late in the day.
On weekend mornings, we’re coming back for breakfast. The Roadkill Skillet and biscuits and gravy are the move. Pair it with their fruit sangria or a Bloody Mary. They now serve cocktails, too.
Insider tips:
The next morning, we’re getting breakfast at the Kitchen Table’s sidewalk cafe. Chef Aaron Wolf runs the kitchen, and the whole place has a sense of humor. Inside, there are hundreds of cheeky signs on the walls, and the staff will toss a joke right back at you.
You have to order the Lobster & Asparagus Benny. It was featured on America’s Best Restaurants, and it’s ridiculously good. If you like a little heat, get the Hot Mother Clucker, a Nashville hot chicken biscuit Benedict, with extra gravy. The Hangover Hash has a serious fan club, and if you want something sweet, the Birthday Cake Pancakes or the cornflake-crusted Apple French Toast will make your morning.
Then we’re doing it right: a Bloody Flight or a Coffee Flight for the table, and a round of Breakfast Shots. The Breakfast Shot is a Kitchen Table tradition. You’ll see tables raising them for birthdays and celebrations, and friends of mine toast a lost friend every single time they come in.
Insider tips:
If you’re in the mood for something laid-back, we’re heading to Prescott Tap. It’s a classic sports bar with about 25 TVs and 16 drafts of Wisconsin and Minnesota beers, served in frosted mugs. Out back, there’s a relaxed patio with bean bags and plenty of seating. It’s the kind of place where one beer turns into an afternoon.
It’s known for burgers and pizza, and both deliver. Build your own burger. Yes, peanut butter and bacon jam are options, and yes, you should try it. The handmade 12-inch pizzas are great too, especially the Deluxe. Whatever you do, we’re getting the smothered waffle fries with homemade queso. I’m telling you, the queso is insane. Friends swear by the BBQ nachos and the wings, which are brined in-house and absolutely massive.
Insider tips:
Muddy Waters has three levels of deck overlooking the river, and people around here call it the best deck in the area. It has a blues theme, a ton of history, and live music out on the patio all summer long.
On a warm afternoon, we’re heading down to the lowest level, the Backwaters. It’s an outdoor tiki bar right by the water with its own lighter menu. Grab a house red sangria, kick back, and watch the boats go by. If you ever get lost, just ask anyone in town where the Backwaters is.
For dinner, we’re heading up to the main restaurant. Start with Leon’s House Smoked Salmon. It’s my favorite, and they even sell it by the half pound. The “Bite Me” Beef Tips with béarnaise and the Baked Brie in puff pastry are musts, too. On Friday and Saturday nights, the house-smoked prime rib is the reason to come. Get the au gratin potatoes on the side, and finish with a Manhattan or a chocolate martini.
Insider tips:
This is pure vacation, right on the water. The Shrimp Shack has been family-owned since 1999, and it’s all about one thing: jumbo broiled shrimp, dusted with a secret seasoning and served with warm butter and house cocktail sauce. My go-to trick is to dip each shrimp in cocktail sauce first, then butter.
Grab a seat on the deck, or when the river allows, head down to the waterside tables with bright Caribbean chairs and tiki umbrellas. You can literally kick off your shoes and put your feet in the water. Pair your shrimp with a Key West Margarita or a Dirty Banana. Kids love the mocktails, especially the Shark Attack.
Insider tips:
Pier 500 sits right on the riverfront in downtown Hudson, and the patio views are some of the best on the St. Croix. On a warm evening, it’s the kind of place where one drink turns into dinner and dinner turns into dessert.
A friend brought her husband here for their anniversary and couldn’t stop raving about the lavender martini and prime rib. The lobster bisque is another favorite.
What to order: The lavender martini, prime rib, and rotisserie chicken are house specialties.
Good to know: In winter, they set up cozy outdoor igloos, so patio season never really ends. Watch where you park downtown. Tickets are common.
With its log-cabin interior and outdoor decks overlooking the river, the Smilin’ Moose feels like a north woods lodge dropped into downtown Hudson. It’s lively, casual, and great for a group.
What to order: The pot roast with homemade mashed potatoes, and upgrade to the street corn.
The first restaurant you’ll pass on your way into historic downtown Hudson, LoLo has outdoor seating and a menu that punches above its weight.
What to order: The Kung Pao chicken rice bowl and a side of rosemary fries with aioli. Save room for a craft cocktail.
The Harbor View is a Great River Road legend, and the patio is half the experience. There’s almost always a wait, but friends say it hardly matters: grab a drink outside and watch the boats and trains roll by along the Mississippi.
What to order: The scallops. Everyone who’s had them raves.
Good to know: Open Thursday through Sunday only. Plan for a wait on weekends.
Sitting in the piazza at Villa Bellezza feels like a trip to Italy. String lights, Italian music, and a fountain in the middle of the courtyard make it one of the most romantic outdoor dining spots in the region.
What to order: A bottle of their wine and the smoked salmon pesto pizza. Save room for tiramisu or the flourless torte.
Good to know: Dog-friendly on the patio, with shaded seating under the loggia and umbrellas.
Not every patio needs a full menu. Grab a slice of pie and a coffee, then find a seat outside and soak in small-town Stockholm. The double lemon is perfect on a warm day.
Good to know: Closed Tuesdays and Wednesdays.
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.
