A Guide To The Perfect Weekend in Iowa
When most travelers think of the Midwest, their minds often leap to Chicago’s skyline or Minneapolis’s lakes. Yet in the middle of America, Iowa’s towns and cities invite you to slow down and discover their unique charms. This isn’t a state you simply pass through; it is one you experience at the pace of a winding road trip. In Iowa, big cities feel welcoming instead of overwhelming, small towns overflow with character, and landscapes roll gently toward rivers and bluffs that surprise first-time visitors. A weekend here can be as diverse as it is refreshing: art-filled mornings in the capital, afternoons of historic bridges and wineries in a storybook county, and evenings spent overlooking the mighty Mississippi River. If you are ready to trade crowded tourist spots for a more genuine and laid-back adventure, then buckle up because Iowa has the perfect weekend waiting for you.
Day 1: Des Moines
Start your Iowa weekend in the capital city, Des Moines. This energetic yet approachable city is filled with art, history, and good food, making it the perfect launching point.
Ease into your trip with a visit to the John and Mary Pappajohn Sculpture Park, a 4.4-acre green space dotted with more than 30 large-scale contemporary artworks. It is free, easy to wander, and right in the heart of downtown. The park makes for a relaxing walk, where you can snap photos of quirky sculptures against the city skyline. On sunny days, you will often see locals lounging on the grass or picnicking nearby, which gives the park a lively, community feel.
Just a short drive away, the Des Moines Art Center showcases an impressive collection of modern and contemporary art, with pieces by legends like Georgia O’Keeffe, Edward Hopper, and Andy Warhol. Admission is free, and the museum’s architectural design alone is worth the stop, featuring buildings designed by three renowned architects: Eliel Saarinen, I. M. Pei, and Richard Meier. Spend an hour or two exploring the galleries, then venture off to the outdoor sculpture garden behind the museum, where tranquil landscaping complements the artworks.
For lunch and an afternoon of browsing, head to Des Moines’ East Village. Grab a bite at Zombie Burger, known for its playful takes on burgers and shakes, then grab a coffee and do a little shopping at Vibrant Coffeehouse plus Kitchen, which houses a retail shop inside. Afterward, take a scenic stroll along the Des Moines Riverwalk. This paved trail follows the river through downtown, connecting to several public art installations and the beautiful World Food Prize Hall of Laureates. It is a peaceful way to see the city from a new perspective.
Before leaving town, treat yourself to dinner at Centro, a local favorite for Italian-inspired dishes with a modern twist. Their wood-fired pizzas and house-made pastas never disappoint. If you are staying overnight in Des Moines, book a room at the Surety Hotel, a stylish boutique property set in a historic building downtown. With its cozy rooms, craft cocktails in the lobby bar, and walkable location, it is a great base before your weekend journey continues.
Day 2: Madison County and Winterset
On your second day, take a short, scenic drive southwest of Des Moines to Madison County. Known for its iconic covered bridges and literary fame, this area offers a picture-perfect slice of Iowa. Made famous by the novel and film, the covered bridges of Madison County are as romantic in real life as they are on screen. Six historic bridges remain, each with its own story. Roseman and Holliwell bridges are two of the most visited, and driving through the countryside to find them feels like stepping into another era.
The town of Winterset, the county seat, has a charming historic square lined with boutiques, cafes, and antique shops. Stop at the Madison County Courthouse, a beautiful 19th-century building that anchors the square, then wander into local stores for handcrafted goods. Don’t miss the Winterset Cidery, where you can sip locally made hard ciders in a relaxed setting, or Rosa’s Boutique, a local favorite offering thoughtfully curated gifts and home décor. The square often hosts seasonal festivals and markets, so check the local calendar when you visit.
Winterset also happens to be the birthplace of Hollywood legend John Wayne. Fans of classic Westerns will love touring the small but well-curated museum, which houses memorabilia, costumes, and personal items from the actor’s career. For an extra dose of nostalgia, step into the modest four-room home where Wayne was born in 1907.
If time allows, take a short detour to one of Madison County’s wineries, such as Covered Bridges Winery, which produces award-winning wines using locally grown grapes. It is the perfect place to unwind with a glass while admiring Iowa’s scenic countryside.
Cap off your Madison County visit with dinner at Urban on the Square, a delightful gem nestled in Winterset’s historic square. With its elegant yet approachable ambiance, this spot serves inventive American fare and offers a hint of upscale charm, making it ideal for both celebratory and relaxed dinners. For a place to stay, the Covered Bridge Inn offers a cozy, family-run retreat just outside Winterset.
Day 3: Dubuque
After exploring central Iowa, head east to the Mississippi River town of Dubuque. Known as one of the oldest cities in the state, Dubuque blends riverfront scenery with fascinating history and vibrant arts.
Kick off your day with a ride on what is often called the “shortest and steepest railway in the world.” The Fenelon Place Elevator is a funicular that carries visitors up a steep bluff, rewarding them with panoramic views of downtown Dubuque, the Mississippi River, and even neighboring states on a clear day. At the top, you will find quiet residential streets that feel far removed from the busy riverfront below.
Dubuque’s connection to the river runs deep, and the National Mississippi River Museum and Aquarium is the best place to experience it. Interactive exhibits highlight the ecology, history, and culture of the Mississippi River, while aquariums feature native species and touch tanks for families. The museum also includes a historic dredging boat and outdoor exhibits that bring the river’s story to life.
In the afternoon, wander through the Historic Millwork District. Once home to thriving lumber and millwork companies, this area has been revitalized with art studios, restaurants, and breweries. Grab a meal or a craft beer at 7 Hills Brewing Company before continuing your exploration. For those who love architecture, the district’s restored warehouses and brick streets provide plenty of photo opportunities.
For a quieter moment, make a stop at the Dubuque Arboretum & Botanical Gardens. This community-run garden showcases a wide variety of plants, from rose gardens to hostas, and it is free to visit. It is a lovely way to spend an hour outdoors, especially during spring and summer when the gardens are in full bloom.
As your weekend winds down, head to the riverfront for a peaceful sunset stroll along the Mississippi. The riverwalk offers benches and overlooks where you can pause to take in the view. If you choose to stay the night, the Hotel Julien Dubuque is a historic and elegant downtown hotel known for hosting guests like Abraham Lincoln and Mark Twain. Its spa, restaurant, and river views make it a wonderful place to end your Iowa road trip in comfort.
Wrapping Up The Perfect Weekend In Iowa
A weekend in Iowa is proof that the best adventures don’t always require crossing oceans or chasing neon lights. Here, art and architecture stand proudly in the capital city, while covered bridges and small-town squares bring literature and history to life in Madison County. By the time you are watching the Mississippi River glow at sunset in Dubuque, you’ll realize Iowa’s magic lies in its variety and warmth. It is in the easy smiles of shopkeepers, the quiet beauty of the countryside, and the simple joy of finding unexpected treasures at every stop. Whether you came for culture, scenery, or just a new place to explore, Iowa sends you home with a sense of discovery.
