Wisconsin's Charming City Near Madison Offers A Walkable Downtown, Shops, And Restaurants

Although most people visit South Central Wisconsin for the more popular state capital of Madison, the region is also home to quieter destinations that showcase history and community in their spaces. After exploring the hot tourist spots, why not set your sights on the smaller cities such as Dodgeville in Iowa County? Nestled in the heart of Wisconsin's Driftless Area, Dodgeville is about a one-hour drive from Madison and Dane County Regional Airport. You'll still be in proximity to the amenities of the bigger city while also enjoying the homey city.

With a 2025 population of about 5,000 (via World Population Review), Dodgeville is the largest community in the county. Learn the ins and outs of the city by taking a walk through the city's historic downtown. Main Street includes the Iowa Street Historic District, listed on the National Register of Historic Places, where you'll find historic buildings. You can take a walking tour of downtown for an opportunity to see these houses, plus the Iowa County Courthouse, the oldest courthouse in Wisconsin.

Beyond its rich history, downtown is filled with personality from the shops and boutiques to the local eats. You'll find some of the top eats on North Iowa Street are neighbors and across the street from each other. On the same stretch, the boutiques surround the restaurants, food trucks, and cafes. If you want to go beyond North Iowa, like White Rose Annex 328 for your souvenirs, it's just a 10-minute walk away.

In the downtown area, you'll find most of your dining options on North Iowa Street. The spots are all close to each other, so you can take your pick depending on the mood or go on a foodie adventure, hopping from one locale to another. The 2025 Dodgeville Visitor Guide recommends Cathryn's Market as the place to go for the true taste of Dodgeville. The market is a hodgepodge of various items, ranging from coffee and breakfast to baked goods and ice cream.

Start your day with a coffee and a sandwich at the Cook's Room Cafe. They offer specialty coffees, salads, and sandwiches that come in a variety of combinations you can do. For lunch or dinner, Corralejo Mexican Grill and Bob's Bitchin BBQ are great options downtown. The first spot is all about festive interiors and generous portions of Mexican cuisine, while Bob's Bitchin BBQ serves up all kinds of barbecue, eight original sauces, and some of the best cheese curds, as one Yelp review says.

If you're doing a spot of shopping, there are antique stores like BPA Boutique across the street from Cook's Room Cafe. Next door is Sprinkled With Style that also doubles as Steph's Sweet Treats Bakery, a boutique and bakery all in one. Both shops have an assortment of clothes, accessories, and even some home goods. For more home decor and antiques, Roots to Branches may be your best bet.

Whatever season you visit, there's something to do in the city. In April, there's the annual Wisconsin Grilled Cheese Championship. Celebrating all cheese lovers, the event features the highlight grilled cheese competition, vendors and exhibitors, entertainment, and more food that's not cheese. If you missed the event, you can still pop by Schurman's Wisconsin Cheese to sample the local cheese. The Dodgeville Farmers Market is also open from May to October and takes place on Saturdays from morning to noon. Looking to sample more of Wisconsin's foodie scene? Dane County Farmers' Market, America's largest producer-only farmer's market, can be found in Madison. To round out the summer, July has the Dodgeville Town Square festivities. The whole thing spans two weeks with a lot of different events you can join. There's live music, entertainment, and events hosted by different local downtown businesses.

Beyond the downtown area, Dodgeville is also home to numerous parks and the Governor Dodge State Park. The state park is 4 miles from downtown and is great for anyone looking for outdoor adventures in the area. On land, you can go hiking, biking, or horseback riding. There are also lakes where you can get in the water for swimming, boating, canoeing, or kayaking. Don't miss out on the other nearby destinations in South Central Wisconsin. Down South, there's Mineral Point with its Cornish cottages, bluffside trails, and a thriving arts scene. North of Dodgeville, you'll find Spring Green, known as the "Wisconsin Desert,'" full of unique attractions.