- Exploring the hidden gems of Western Wisconsin—curating unforgettable stays and sharing the places locals love most.
The first time I walked into the Sheldon Theatre, I actually stopped in the aisle. You come in off a regular downtown street in Red Wing, and suddenly you’re standing in a gilded jewel box from 1904: a painted proscenium, ornate balconies, warm light everywhere. It’s small enough that there isn’t a bad seat, and grand enough that it feels like an occasion.
It’s about 35 minutes from Prescott, which makes it one of my favorite date nights to recommend to guests. Here’s how to plan the whole evening, from the drive down to the nightcap after.
The Sheldon opened on October 10, 1904, with a comic opera called The Royal Chef. It exists because of one man’s will: T.B. Sheldon, a Red Wing businessman who died in 1900, left a large share of his estate to the city for a public purpose, and Red Wing chose to build a theater. That makes it one of the first municipally owned theaters in the country, and the city still owns it today.
It has had a dramatic life. A fire in 1918 led to a refurbishment and a projection booth. In 1936 it was remodeled for movies. In 1988 it was restored as a performing arts theater, and a major renovation finished in 2018 brought back the original proscenium murals, the decorative paintings and historically accurate floors. One of its directors likes to joke that the Sheldon “has burned twice and exploded once.” You’d never know it now.
The architecture is Renaissance Revival, designed by Lowell Lamoreaux, and the theater seats 468. It’s on the National Register of Historic Places, and about 30,000 people come through its doors each year.
Insider tip: Arrive early enough to spend five minutes just looking at the ceiling and the proscenium. Ask an usher about the murals. They love talking about the restoration.
The Sheldon books a little of everything: touring musicians, comedians, dance, magic and holiday shows. Shows announced for the 2026–27 season include Continental Ballet’s The Nutcracker in mid-December, comedy from Tommy Ryman at the end of January, Black Angels Over Tuskegee in late February, and Minnesota favorite Dessa in early March. Schedules change, so check the Sheldon’s own calendar before you plan your trip.
The box office is open Wednesday through Friday afternoons and Saturday midday. Book ahead for anything popular. With 468 seats, the good ones go quickly.
The prettiest way is the river. Take Highway 35 south along the Mississippi to Hager City, then cross the bridge on Highway 63 into downtown Red Wing. It’s about 35 minutes, with the bluffs on one side and the river on the other.
For the drive home in the dark, take Highway 61 north on the Minnesota side to Hastings, then Highway 10 east back into Prescott. Both routes are easy and about the same time.
The St. James Hotel, built in 1875, is a short walk from the theater and feels like it belongs in the same story. Scarlet Kitchen and Bar has river views and a menu from an executive chef and a dedicated pastry chef, so save room for dessert. If you’d rather keep it casual, Red Wing Brewery is known for its beer and pizza.
After the curtain, walk back to the St. James. The hotel’s cocktail lounge is romantic and historic, with cocktails, charcuterie and small plates, and it’s the perfect place to talk about the show.
Red Wing is also home to the second shop of Stockholm Pie, the little Wisconsin pie shop that’s been named best pie shop in America. Pick up a slice for breakfast tomorrow, or better yet, a whole pie for your room.
The Sheldon is a perfect Saturday night inside a bigger river weekend. Spend Saturday morning on Prescott’s Broad Street, take the river road south in the afternoon, catch a show in Red Wing, and come home to Prescott for a slow Sunday. On Sunday, walk up to Freedom Park where the St. Croix meets the Mississippi, and finish with brunch at Prescott Tap or a long breakfast at The Kitchen Table.
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.
