Dinner and a Show: A Wisconsin Night Out

Though a movie on the couch may seem like a cozy option, the Wisconsin performing arts scene is sure to be a thrilling—and theatrical—way to get out on Saturday night. Reserve your seat for an evening of guaranteed entertainment. After all, what better way to get out and about than with some good ole show tunes.


Swap your night in for a night on the town with two Madison favorites: the Madison Opera and Forward Theater, both making their home at the Overture Center for the Arts. Whether you’re looking for a night of operatic classics or an evening of thought-provoking entertainment, both showcase the best creative talents in Madison, focusing on making the performing arts an exciting experience for all audience members.

Before the curtain goes up, start your artistic journey at the Madison Museum of Contemporary Art. Or, for those fans of the boozy persuasion, take a tour of the Capital Brewery in Middleton, where beer is their chosen art form. For the perfect pre-show meal we suggest one of the spectacular dining locations near the Overture Center, like The Icon, a deliciously simple Spanish tapas bar, or Cento, an Italian restaurant.

After the show, conclude your evening of entertainment by grabbing a basket of cheese curds at Tipsy Cow or ordering an Old Fashioned with a side of “The Piano Man” at the Ivory Room featuring dueling pianos.


Take to the streets of Wisconsin’s largest city, where homegrown performers, decadent dining and handcrafted cocktails set the stage for the perfect night out. Milwaukee is home to some of the oldest and most diverse performing groups in the state. Prepare yourself for an authentic take on classic and modern plays at the Milwaukee Chamber Theatre, where their casts are primarily made up of Wisconsin actors. Or, if you prefer to be dazzled by music and dance, be transported to another world by the lights, costumes and artistry of the Milwaukee Ballet.


Planning a day trip for pre-show exploring? Take a walk through the iconic Milwaukee Art Museum, or make a stop at the Pfister Hotel to chat with the artists in residence. After an afternoon out and about, warm your toes at one of Milwaukee’s fine dining locations. For a romantic night out, reserve your table at the Five O’Clock Steakhouse for a nationally-ranked steak dinner and glass of wine.

For a post-show munchies solution, retire to the Rumpus Room for a beer and late night snacks at one of the city’s finest gastro pubs. 

La Crosse

In recent years, La Crosse has greatly developed their art district that sits near the Mighty Mississippi River. Stop in to the Pumphouse Regional Arts Center where popular performances, exhibitions from three art galleries and even classes in art and music await.

Right across the street is the Weber Center for the Performing Arts, home to the La Crosse Community Theatre. Amateur theatre by definition, the shows put on here are nothing short of professional standards. Depending on the weekend you're in town, you may have the chance to catch a concert at the La Crosse Center If the kids are along, walk on over to the Children's Museum to play and learn!

You don't have to head far for creative entree or delectable dessert at Piggy's, which is right in the thick of the arts district. Dine in style at the Freighthouse for the most amazing steak and seafood. 

For a rustic, chic boutique stay with your hunny, book a night at the Charmant with views of Riverside Park. Or if the whole family's along, pop outside La Crosse for a northwoodsy stay at Stoney Creek Hotel. The kids will love being surrounded by wildlife.


Though Lake Michigan may be frozen, the art scene on the shores of Sheboygan is anything but cold. Located in a restored 1928 movie palace, the Stefanie H Weill Center for Performing Arts is a beautiful setting to see everything from big band music to ballet. Or enjoy a performance at the nationally acclaimed John Michael Kohler Arts Center.

Before the show drive through the Wisconsin country side to the American Club Resort in nearby Kohler for lunch at the classic Horse and Plow Restaurant. (Warm up with their beer cheese soup! It’s delicious!) After lunch, explore the exhibits at the Kohler Arts Center in Sheboygan or join in on one of the signature classes, ranging from family-friendly to grownups only.

If you’re looking to explore downtown Sheboygan, we suggest following your nose! Find the fragrant Olivü for an afternoon of personalizing your own natural, homemade lotions, soaps and beauty products.

For dinner before your show, we suggest that you take a trip to Il Ritrovo. Grab a slice of authentic pizza made from all natural ingredients and a wood fired oven. Between the art, food and scenery, you’re guaranteed a standing ovation after a day of exploration in the Sheboygan area.

Find more theater and performing arts venues or tell us about your favorites in a comment below.