Small Towns With Real History and Character
The Driftless Region is known for preserved downtowns, early mining settlements, and towns that never got flattened into generic strip malls. Many of these places still have original buildings, walkable streets, and strong local identity.
These are some of the most historically interesting towns to explore in southwest Wisconsin and nearby areas.
Mineral Point, Wisconsin
Website
https://mineralpoint.org
One of the oldest communities in Wisconsin, originally built as a lead mining town in the early 1800s.
What Makes It Historic
- Stone buildings from the mining era
- Cornish immigrant influence
- Preserved downtown layout
- Active arts community in historic structures
What to Do
- Walk the historic downtown
- Visit small galleries and studios
- Explore Pendarvis Historic Site
https://www.wisconsinhistory.org/Records/Property/HI1609
Mineral Point feels more like a preserved European village than a typical Midwest town.
Spring Green, Wisconsin
Website
https://springgreen.com
A small town known for architecture, theater, and its connection to Frank Lloyd Wright.
What Makes It Historic
- Long-standing agricultural roots
- Historic main street
- Nearby cultural landmarks
What to Do
- Visit Taliesin
https://www.taliesinpreservation.org - Explore downtown shops and cafés
- Drive surrounding ridge roads
Spring Green blends rural history with a surprisingly strong arts and design presence.
Viroqua, Wisconsin
Website
https://www.viroquachamber.com
A historic railroad and farming town that evolved into one of the region’s cultural centers.
What Makes It Historic
- Preserved downtown buildings
- Early agricultural trade hub
- Strong cooperative and local-food traditions
What to Do
- Walk the downtown district
- Visit local cafés and co-op
- Use it as a base for exploring nearby valleys
Viroqua has a mix of historic structure and modern small-town revival.
Prairie du Chien, Wisconsin
Website
https://www.prairieduchien.org
One of the oldest European settlements in Wisconsin, located along the Mississippi River.
What Makes It Historic
- Early French fur-trade history
- Mississippi River trading routes
- Military and frontier significance
What to Do
- Visit Villa Louis Historic Site
https://www.wisconsinhistory.org/Records/Property/HI1602 - Walk riverfront areas
- Explore local museums
This town connects the Driftless Region to the larger history of river trade in the Midwest.
Dodgeville, Wisconsin
Website
https://www.dodgeville.com
Historic county seat with roots in the lead mining era.
What Makes It Historic
- Early settlement tied to mining
- Traditional courthouse square layout
- Access point to surrounding rural communities
What to Do
- Walk the downtown
- Use it as a base for visiting Governor Dodge State Park
https://dnr.wisconsin.gov/topic/parks/governordodge
Dodgeville is less touristy but gives a clearer picture of everyday historic Wisconsin.
Why Historic Towns Survived Here
The Driftless Region’s rugged terrain made large-scale industrial development harder. Because of that, many towns kept:
- original street layouts
- early buildings
- smaller local businesses
- community-centered downtowns
In flatter parts of the Midwest, many of these would have been replaced by highways and big-box development.
Tips for Exploring Historic Towns
- Park once and walk
- Visit on weekends for open shops
- Check local event calendars
- Combine towns into a single day trip
Most of these places are within 30–60 minutes of each other.