No one does small-town charm better than these seven quaint spots in Wisconsin. Enjoy a day trip or a weekend away at these small but special towns.
If you Google “What’s in Wisconsin?”, plenty of info pops up about cheese, beer, and the Packers. And while none of that is technically wrong, there’s so much more to Wisconsin than that (although we do all of those things exceptionally well).
Here, we have breathtaking foliage when the seasons change and incredible lakeside views. We also have plenty of small, charming, quaint towns and villages, all with lots of heart and plenty of hometown charm.
All these charming small towns and villages in Wisconsin have populations of fewer than 9,000 folks, but the small, special, and close-knit vibes are endless. So if you’re looking for a Stars Hollow or Mayberry feel for your day trip or long weekend, consider visiting one of these seven charming small towns in Wisconsin.
New Glarus
In Green County, the small village of New Glarus, known as Wisconsin’s little Switzerland, is tucked away—a must-visit for so many reasons. From the town’s deep Swiss roots and quaint chalet-style architectural details to the local brewery and winery, there’s a lot to do in this little town.
Home to the one and only New Glarus Brewing Company, enjoy a free, self-guided tour of the brewery while sipping crisp and refreshing beer.
Not a beer drinker? Never fear. New Glarus is also home to Bailey’s Run Vineyard & Winery and Whiskey Run (conveniently in the same location). After my most recent visit there, I can confidently recommend adding the wine tasting to your to-do list. The wines were unique, fresh, and absolutely delightful.
Wondering how small is small? New Glarus’ population is 3,659.
New Glarus Brewing Company
Location: 218 Hoesly Drive, New Glarus
Hours: Tuesday to Saturday, 10 a.m. to 5 p.m.
Bailey’s Run Vineyard & Winery and Whiskey Run
Location: N8523 Klitzke Road, New Glarus
Hours: Open seven days a week
Mount Horeb
Have you ever wondered if trolls are real? While that may be up for debate, the village of Mount Horeb pays homage to its Scandinavian roots with whimsical, detailed troll carvings throughout the area. In fact, these terrific trolls are so near and dear to the area that a map is available to help you track down each and every troll on your visit.
Mount Horeb is also home to a serene outdoor scene. Amid the Driftless Region, you’ll fall in love with awe-inspiring rock formations and enjoy a stroll through Military Ridge State Trail. Part of a total 40-mile trek, it winds through neighboring areas including Verona (which also made this list).
Wondering how small is small? Mount Horeb’s population is 7,754.
Military Ridge State Trail
Location: 116 South Second Street, Mount Horeb
Lake Geneva
Move over Stars Hollow, Lake Geneva is giving all the cozy, small-town charm that fans of “Gilmore Girls” will absolutely adore. The downtown area is bustling with plenty of small shops for everyone—they even host a special event, We LOVE Local Wednesdays, to support these shops in tangible ways.
Of course, as its name suggests, the heart of Lake Geneva is the actual lake itself. With glistening waves and crystal water, whether you’re boating, jet skiing, or sunning on a sandy beach, you’ll almost forget you’re in Wisconsin.
Visiting during winter or on a rainy day? The Grand Geneva Resort & Spa is a short 10-minute drive from downtown Lake Geneva and is truly a treat. Personally, I can speak to the massage services and facials (of which I’ve enjoyed many). You’ll leave feeling pampered, rested, and revitalized.
Wondering how small is small? Lake Geneva’s population is 8,277.
Grand Geneva Resort & Spa
Location: 7036 Grand Geneva Way, Lake Geneva
Hours: Open seven days a week
Sister Bay
One of the most picturesque places in Wisconsin is Door County, home to Sister Bay. Gorgeous sunsets and crystal-clear waters aren’t the only highlights of a visit here.
You can get a delicious breakfast almost anywhere, but only at Al Johnson’s Swedish Restaurant & Butik (which is a fabulous little boutique) can you get breakfast with goats on the roof. Yes, you read that right—goats on the roof. While all of the food is tasty, the Swedish pancakes with lingonberries steal the show every time.
Also, if you’re visiting between April and August, add a visit to a cherry orchard or market. Both Door County Wildwood Market and Seaquist Orchards Farm Market are between the village of Sister Bay and neighboring Ellison Bay.
Wondering how small is small? Sister Bay’s population is 1,044.
Al Johnson’s Swedish Restaurant & Butik
Location: 10698 N. Bay Shore Drive, Sister Bay
Hours: Open seven days a week
Door County Wildwood Market
Location: 2208 Wildwood Rd, Sister Bay
Hours: Open mid-July through mid-October
Seaquist Orchards Farm Market
Location: 11482 WI-42, Sister Bay
Hours: Open early May through late October
Cedarburg
Cedarburg is the center for small, charming shops and festivals throughout the downtown area. A visit to the historic Cedarburg Woolen Mill, now The Shops of Cedar Creek Settlement, is a must-stop during your trip. Not only are there great shops, but you’ll find a few spots to get a bite to eat.
Your visit won’t be complete without checking out Cedar Creek Winery in the same gorgeous historic space. Previous visitors rave about the luxury and delight of enjoying wine flights—a little bit of everything the winery has to offer.
Wondering how small is small? Cedarburg’s (village) population is 6,180 (the city 12,121).
The Shops of Cedar Creek Settlement and Cedar Creek Winery
Location: N70 W6340 Bridge Road, Cedarburg
Hours: Open seven days a week
Plymouth
Did you know that the Cheese Capital of the World is right here in the tiny town of Plymouth, Wisconsin? Yes, Wisconsinites are more than the clichés of cheese and beer, but we do it really well! When you visit downtown, you can check out the town’s incredible mural collection (spoiler—seven of the gorgeous images involve cheese, dairy, or beer).
Speaking of the latter, if you enjoy beer, make sure to stop by the Plymouth Brewing Company Taproom. Come prepared if you’re feeling a little hungry—food is not available at this location, but you’re welcome to bring your own for your visit.
Of course, a visit to this charming, cheesy little town wouldn’t be complete without a stop by Chester’s Drive-In. A small, family-owned-and-operated spot for incredible butter burgers and custard is a much-needed stop during your stay or on your way home.
Here’s the Plymouth Mural Map.
Wondering how small is small? Plymouth’s population is 8,932.
Plymouth Brewing Company Taproom
Location: 222 East Mill Street, Plymouth
Hours: Open Wednesday through Sunday
Chester’s Drive-In
Location: 1504 Eastern Avenue, Plymouth
Hours: Open daily 10:30 a.m. to 7 p.m.
Huebertus
The village of Huebertus is a small but mighty and marvelous area to visit in Wisconsin. Sitting atop the highest elevation in southeastern Wisconsin, Holy Hill is home to the breathtaking Basilica and National Shrine of Mary Help of Christians. One of the most special sights to see during your visit is the view from the scenic tower overlooking the surrounding Kettle Moraine area.
But before you leave, a stop by the Pine Hill Orchard is in order. Open and family-owned since 1978, the orchard feels like a trip back to a simpler time, with all the apple fan favorites like apple cider, apple pie, honey, maple syrup, and more.
Wondering how small is small? Hubertus’ population is 5,500.
Basilica and National Shrine of Mary Help of Christians
Location: 1525 Carmel Road, Hubertus
Hours: Tower open May to October, daily
Pine Hill Orchard
Location: 5682 State Hwy 167, Hubertus
Hours: Open Saturdays and Sundays, 9 a.m. to 6 p.m.
