These Charming Towns Turn Tourists into Residents

Three idyllic communities near Madison, WI, ooze small-town charm while being an easy drive away from big-city amenities.

By Brittany Anas on July 29, 2023

In Columbia County, Dr. Mary Rose Strickland’s family lives in the country, and her kids can run about and ride their bikes without traffic. Her family has chickens, a large garden and, together, they stay active by biking scenic loops and swimming at Silver Lake Park and Beach in the summers. This small town near Madison has schools, offices, churches and grocery stores within a 15-minute radius, and Madison and its amenities are reachable in 45 minutes.

“You can truly obtain quiet, country living with the conveniences of larger cities,” says Strickland, a wife, mother to two children ages 5 and 4 and a doctor of physical therapy who co-owns and is president of New Life Physical Therapy. The private practice has locations in Portage, Baraboo, Reedsburg and Westfield. 

The eight-county Madison Region indeed offers rich outdoor resources, growing business communities and local traditions. With Madison in its backyard, small to mid-sized communities are attracting newcomers, who benefit from a lower cost of living, ease of access to a growing city and the truth behind the idea that you can be a big fish in a small pond. Close-knit communities with residents eager to volunteer is a bonus, Strickland says.

From the bucolic hiking trails at Governor Dodge State Park to the waterparks in the Wisconsin Dells, it’s no wonder that the region’s smaller communities have a knack for turning tourists to visitors and drawing residents who want to live the good life.

Discover three communities that are small in population, but have a ton to offer.

Portage, WI

Neil Shortreed, owner of Neil’s Wine House, says downtown Portage has a small-town charm and a unique mix of businesses.

“In our community you can find an old-fashioned soda fountain, stop in at a billiards hall, meet the artists at our art gallery, find that perfect new outfit you’re looking for and get an ice cream all within a couple walkable blocks,” says Shortreed, a Wisconsin native.

Set in a historic house, his wine bar is located just at the end of the residential area within the downtown area. There’s an outdoor deck and locals and tourists alike gather for not just wine, but also craft beer, cocktails and meals. “We are a community that is friendly, kind and hard working,” he says.

Portage residents also have access to some spectacular outdoor amenities, Shortreed says, including access to the Wisconsin and Fox rivers and the National Ice Age Trail. Plus, Cascade Mountain, one of the Midwest’s largest ski areas, is not too far either.

Other small, nearby communities like Lodi and Wisconsin Dells, also have charming downtown areas with thriving locally owned businesses. With its many parks, lakes, galleries and resorts, Columbia County has established itself as a beloved Midwest travel destination.

Baraboo, WI

Sauk County has become one of the region’s fastest-growing areas, yet it still retains small-town character.

Known for its scenery and natural wonders, outdoor lovers are especially drawn to Baraboo, another great small town near Madison that is home to Devil’s Lake State Park, Wisconsin’s largest and the Midwest’s most visited state park. Visitors can take in panoramic views from 500-foot quartzite bluffs that overlook the 360-acre lake. The park has 30 miles of hiking trails, plus lakeshore picnic spots and swimming beaches.

Baraboo also has plenty of museums, restaurants and shops to enjoy, plus community traditions that bring neighbors together – like the “Concerts on the Lawn” summer music series, a holiday light parade and a wine walk and shop event.

Dodgeville, WI

Katie Mosley opened Kate’s Bait & Sporting Goods in Dodgeville a decade ago, inspired by the family trips she took as a kid and fond memories of walking into bait shops and feeling like vacation had commenced. Her latest addition to her own shop is a seasonal ice cream parlor.

Mosley says she loves answering questions for tourists just as much as she likes bringing locals together in a laid back setting. She enjoys hosting and participating in community events like a Winter Ice Fishing Derby, a Fall Festival and a Chili Cook-Off.

The region, she says, is home to several unique attractions, from esteemed architect Frank Lloyd Wright’s architectural masterpieces (Taliesin, Wright’s famed home and studio is in nearby Spring Green) to the hills, bluffs and waterfall in Governor Dodge State Park. 

“My house sits on the outskirts of the park and my husband and I can take a walk on one of the many trails and feel we are miles away,” she says. “It’s such a beautiful area.”