10 Wisconsin Small Towns With Big Shopping Appeal


There is a way to enjoy holiday shopping rather than stressing over it, and it’s called the “shop-cation.” Wisconsin’s version of the shop-cation includes quaint small towns you’ve always wanted to visit with streets lined by charming independent shops, cozy restaurants and boutique inns. Also included are two urban neighborhoods that provide a taste of small-town charm inside the big city. Here are 10 top destinations to put on your list.

Cambridge: Originally settled by Scottish and Norwegian farmers, today this small town has a strong artistic community.

Mineral Point: This was the first city in Wisconsin to be listed on the National Register of Historic Places. The list of art studios and galleries would be impressive even for a big city.

Spring Green: Known for Frank Lloyd Wright’s Taliesin, the American Players Theatre and the quirky House on the Rock, it also has some real hidden gems of shopping.

  • SHOP Arcadia Books is an independent bookstore with a café and coffee shop. The Opal Man jewelry boutique is the only independent opal dealer in the U.S. The visual merchandising at Convivio will make you want the home décor items even more.
  • EAT An espresso at Driftless Depot is a good way to start the day, and don’t pass up the scones. The General Store is a 1910 converted cheese warehouse serving old-school comfort food with a twist. Finish up with a slice of pie at Bird of Paradise Tea.
  • STAY The Round Barn and The Usonian Inn were both designed by associates of FLW. The Silver Star B&B is a lodge with original fine art and photography throughout.

Baraboo: Shop fronts haven’t changed much since the city bustled with the excitement of being the winter home for the Ringling Brothers circus. Today, the historic downtown county courthouse square is a pleasing potpourri of shops and galleries.

Washburn and Ashland: Just 15 minutes apart on Lake Superior’s Chequamegon Bay, these make for an easy pair. Washburn is a secluded community on the north shore of Chequamegon Bay on Lake Superior and the nation’s first eco-municipality. Ashland is the “historic mural capital of Wisconsin.”

Hudson: Set on the banks of the St. Croix River, this quaint river town used to be called Buena Vista because of the beautiful views.

Green Lake Country: This is actually five pretty little cities – Green Lake, Ripon, Princeton, Berlin and Markesan – each with their own unique charm.

Viroqua: This laid-back little community, with a downtown big on arts, sustainable goods and surprising finds, lies in the center of one of the greatest organic farming regions of the U.S.

Madison’s Monroe Street: In the shadows of storied Camp Randall Stadium, this neighborhood exudes independent charm and a hip vibe.

  • SHOP Orange Tree Imports is the “it” spot for cookware, kitchen gadgets and home entertaining finds. Velvet Button Boutique has stylish apparel and one-of-a-kind handmade jewelry and handbags. Art Gecko is known for its clothing and textiles from around the world hand-sourced by the owner. Wild Child has natural fiber clothes for babies and tots and super-cute toys. Maurie’s Fine Chocolates, need we say more?
  • EAT Savor every sip of the pour-over coffee at Crescendo. For lunch, Gates & Brovi is the casual restaurant project from two James Beard nominees.
  • STAY HotelRED is an ultra-contemporary boutique hotel and restaurant. Mendota Lake House B&B is a model for using locally sourced fresh and organic products.

Milwaukee’s Third Ward District: Once a warehouse district and now known as Milwaukee’s arts and fashion district, this neighborhood is bordered by the Milwaukee River, the Lake Michigan harbor and Milwaukee’s downtown.

SHOP Stephanie Horne Boutique, Lela Boutique, and Stella's Trunk specialize in women’s apparel. Hot Pop has quirky toys and gifts. Embelezar has an incredible mix of home pieces, plus 3rd Ward Jewelry is right next door. Wrap your gifts with paper and ribbons from Broadway Paper.

EAT Bella Caffe has great coffee and “exquisite desserts.” Holey Moley Coffee + Doughnuts is the city’s only craft doughnut shop. Grab lunch at Milwaukee Public Market.

STAY The Pfister Hotel is a historic icon with an expansive Victorian art collection. There’s also the Art Deco boutique property Hotel Metro with roomy suites.


How about even more shopping suggestions? Try these boutiques around the state.