10 Coolest Small Towns in Wisconsin for a Summer Vacation
Wisconsin's vacation appeal runs well past the cheese-and-beer reputation. The ten towns ahead reach across the Door Peninsula, the Northwoods, the Driftless Area, and the Lake Superior shore. Some run on Swiss or Swedish founding history. Others draw on shipbuilding, road racing, or the Frank Lloyd Wright archive. Each one earns a summer-trip slot for a specific reason.
Bayfield
Bayfield sits at the north end of the Bayfield Peninsula on the south shore of Lake Superior with about 530 year-round residents. The town is the mainland gateway to the Apostle Islands National Lakeshore, which covers 21 of the 22 islands in the Apostle archipelago plus 12 miles of shoreline on the peninsula. Madeline Island, the largest in the chain and the only one with year-round residents, is the one island not in the Lakeshore. The Madeline Island Ferry leaves from the Bayfield ferry dock several times a day for the crossing to La Pointe.
Rittenhouse Avenue runs the small downtown grid up the hillside from the lake with independent shops, restaurants, and the working sailing fleet visible through every gap in the storefronts. Big Top Chautauqua, an open-air canvas tent venue on Mount Ashwabay south of town, runs about 75 concerts and shows every summer. The Bayfield Apple Festival on the first weekend of October draws roughly 50,000 visitors, the largest single event of the year for a town that normally has 530 residents.
Elkhart Lake
Elkhart Lake holds about 1,000 residents on the east shore of its namesake spring-fed lake in Sheboygan County. Road America, the four-mile permanent road racing circuit just outside the village, has run on its current 640-acre site since 1955. The track hosts NASCAR, IMSA SportsCar, IndyCar, and AMA Pro Racing events and remains one of the longest natural-terrain road courses in North America.
The lake water is among the clearest in southeastern Wisconsin, fed by underground springs that hold visibility down to about 25 feet in calm summer water. The Osthoff Resort on the south shore handles the larger lodging end. The Shore Club's Tiki Bar runs the lakeside cocktail-and-sunset routine in summer. The Paddock Club downtown handles fine dining, and Lake Street Cafe runs the morning breakfast crowd.
Fish Creek
Fish Creek sits in the middle of the Door Peninsula on the Green Bay side, with the limestone bluffs of the Niagara Escarpment rising directly behind the village. Peninsula State Park borders the village on the north and east and covers 3,776 acres of woodland, shoreline, and bluff. The park's Eagle Tower, rebuilt in 2021 as a 60-foot wooden observation tower with a 1,000-foot accessible canopy walk, is one of the most reliable Door County views.
The Eagle Bluff Lighthouse inside the state park has run continuously since 1868 and operates as a museum maintained by the Door County Historical Society. Northern Sky Theater (renamed in 2014 from its earlier American Folklore Theatre identity) performs original Wisconsin-themed musicals in an outdoor amphitheater inside the park and is the village's signature summer attraction. The downtown grid along Highway 42 runs about three blocks of independent shops, galleries, and restaurants.
Hayward
Hayward sits in Sawyer County in the heart of the Northwoods with about 2,600 year-round residents and a summer population that runs several times that. The Freshwater Fishing Hall of Fame on East 1st Street is the working anchor, with a half-acre walk-through fiberglass muskie that has been the town's signature photo stop since it opened in 1979. The muskie measures 143 feet long, four-and-a-half stories tall, and visitors can walk up through the body to a viewing platform inside the open jaws.
The Chequamegon side of the Chequamegon-Nicolet National Forest covers about 858,400 acres of the surrounding Northwoods and runs the fishing, hunting, and ATV routes that pull most of the summer crowd. Lac Courte Oreilles, a 5,000-acre lake just south of town, is one of the better muskie and walleye fisheries in the upper Midwest. The American Birkebeiner cross-country ski race in late February draws around 12,000 skiers across the 50-kilometer skate, 55-kilometer classic, and shorter Korte and Prince Haakon distances, with the finish line on Main Street in downtown Hayward.
Minocqua
Minocqua occupies a peninsula on Lake Minocqua in Oneida County, with the lakefront downtown connected by a bridge to the rest of town. The "Island City" tag goes back to the 1880s, when the village was reachable only by water until the railroad bridge connected it in 1887. The town runs about 4,400 year-round residents and triples that count during the summer water-recreation season.
The Thirsty Whale Restaurant on Front Street has run on the harbor since 1968 with a deck that fills the lake-facing side of the property. Rocky Reef Brewing Company on Highway 51 just north of downtown runs the local craft beer operation. The Northwoods Children's Museum on Oneida Street draws families with younger kids. Wildwood Wildlife Park on Highway 70 west of town is the seasonal zoo-and-petting-farm operation that has run since 1957.
New Glarus
New Glarus sits about 25 miles southwest of Madison with a population of about 2,200 and a Swiss founding history that the town still actively celebrates. The village was founded in 1845 by 108 Swiss immigrants from the Canton of Glarus in eastern Switzerland and called itself "America's Little Switzerland" in tourism materials by the early 20th century. The Swiss Historical Village Museum holds 14 buildings on the original colony site.
New Glarus Brewing Company on County Highway W is the largest craft brewery in the country that distributes in only one state. The brewery's Spotted Cow farmhouse ale has been Wisconsin-only since the brand's launch in 1997. Volksfest the first weekend of August and the Wilhelm Tell outdoor drama on Labor Day weekend are among the longest-running ethnic festivals in the state. Maple Leaf Cheese and Chocolate Haus and the Glarner Stube restaurant round out the daily lineup.
Sister Bay
Sister Bay holds about 1,000 year-round residents on the Green Bay side near the north end of the Door Peninsula. Al Johnson's Swedish Restaurant on Bay Shore Drive runs goats on its sod roof during the warm months, a tradition that goes back to 1973 and is now a registered trademark of the restaurant. The Swedish menu inside has stayed largely unchanged since the restaurant opened in 1949.
The village runs one of the largest harbors on the Door Peninsula's Green Bay side, with a free public beach next to the marina. Door County Bakery on Highway 42 handles the morning pastry routine. The Sister Bay Fall Festival the third weekend of October is among the largest seasonal events on the peninsula. Marina Park hosts free concerts on the waterfront most Tuesday nights from June through August.
Spring Green
Spring Green sits in the Driftless Area along the Wisconsin River about 40 miles west of Madison. Taliesin, Frank Lloyd Wright's home and studio, covers 800 acres of the rolling country south of town and earned UNESCO World Heritage designation in 2019 as part of "The 20th-Century Architecture of Frank Lloyd Wright." Tours of the main house, the Hillside Studio, and the surrounding agricultural buildings run May through October.
House on the Rock, the 240-acre attraction east of town built by Alex Jordan Jr. between 1945 and his death in 1989, is the strangest large tourist attraction in Wisconsin. The site holds the world's largest indoor carousel with 269 animals, none of them horses. American Players Theatre on Spring Green's north edge runs classical theater in a 1,089-seat outdoor amphitheater on a wooded hillside through the summer and fall season.
Stockholm
Stockholm holds a year-round population of about 60 on the east bank of Lake Pepin, the 22-mile natural widening of the Mississippi River that separates Wisconsin from Minnesota. The town was founded in 1854 by Erik Peterson of Karlskoga, Sweden, who led one of the first organized Swedish settlement efforts in the upper Midwest.
The Stockholm Pie and General Store on Spring Street is the village's signature stop, named one of America's best pie shops by the Food Network in 2014. Maiden Rock Bluff State Natural Area on Highway 35 just south of the village covers 391 acres with a bluff-top overlook of the lake. The Great River Road, which Stockholm sits along, has been designated an All-American Road by the Federal Highway Administration since 2021.
Sturgeon Bay
Sturgeon Bay is the seat of Door County and the largest city on the peninsula with about 9,500 residents. The Door County Maritime Museum on Madison Avenue covers regional shipbuilding history with operating displays of small craft, navigation equipment, and a full-scale tugboat. Fincantieri Bay Shipbuilding on the east side of the harbor still builds and repairs Great Lakes commercial vessels and is the largest active shipyard on the western Great Lakes.
The Sturgeon Bay Ship Canal cuts across the peninsula to Lake Michigan and is bracketed by two working lighthouses, the Sturgeon Bay Pierhead Light and the Sturgeon Bay Canal Light. Potawatomi State Park on the bay-side edge of the city covers 1,200 acres of forest, shoreline, and a 75-foot observation tower. The Saturday Farmers Market downtown runs May through October on a third-street block above the working harbor.
What These Ten Have In Common
The ten split into rough regional clusters. Door County produces Fish Creek, Sister Bay, and Sturgeon Bay along the limestone peninsula. The Northwoods produces Hayward and Minocqua in the inland forest belt. The Lake Superior coast produces Bayfield and its island chain. The Driftless Area and Mississippi River bluffs produce Spring Green and Stockholm. Southern Wisconsin produces Elkhart Lake and New Glarus. Each town runs on a specific anchor that has held for at least 50 years and gives the summer trip a real reason to go.
