Craving a weekend trip away from Milwaukee’s hustle and bustle? You’re in luck. Lake Michigan’s gorgeous beaches and shorelines extend past the capital’s skyscrapers to a number of quaint towns and cottage destinations.
Our favorite of the mix? Sheboygan, hands down. Our Sheboygan vacation rentals welcome you with comfort to the town’s stunning coastlines, historical attractions, and outdoor activities.
In this guide, we’ve rounded up our favorite small towns for weekend getaways and day trips from Downtown Milwaukee.
1. Sheboygan
Photo Credit: James Meyer
- Sheboygan, WI
- Best for: Nature, fishing, and historical downtown area
The town of Sheboygan is famous for its surfing, fishing, and freshwater beaches along the coast of Lake Michigan’s western shore. Sheboygan is the first town in greater Sheboygan County, founded in 1839. What started as a manufacturing hub in the 19th century turned into one of the most popular weekend destinations from Milwaukee.
Here are some reasons Sheboygan is our top weekend getaway from the “Cream City”:
Historical attractions
Any history buffs in the house? American history, contemporary art, and local experts are abound in Sheboygan’s many historical attraction.:
John Michael Kohler Arts Center
John Michael Kohler Arts Center features an “artist-built environment,” where artists from across the country shape the actual surroundings of the center. You’ll find art everywhere, including artist-designed washrooms and the infamous sculpture park.
ACUITY Flagpole
The ACUITY Flagpole stands as the tallest in the county at 140 feet, a must-see historical attraction, and a fabulous photo-op for the family. We also commend the owners’ respect for our veterans, as they recently lowered the flag to half-mast upon the death of a long-time, 80-year veteran to Wisconsin.
Water activities
Surf’s up in Sheboygan year-round, even in the winter months. Known for smooth yet challenging freshwater waves, Lake Michigan’s portion of Sheboygan’s coast is a hotspot for travelers itching for a surf.
Other popular water activities in Sheboygan include:
- Kayaking: We love Esslingen Park for its serene, picturesque river views — the perfect scene for canoeing and kayaking.
- Paddle boarding: Balance skill and thrill with a paddle in Lake Michigan’s gentle waters. EOS Surf can help you out with rentals.
- Fishing: The Sheboygan River is brimming with delicious chinook, salmon, and brown trout for the taking!
Wineries
Another unexpected plus? The delectable wine and scenic wineries. We know what you’re thinking — this is the Midwest, not California. But Wisconsin has some lovely wineries, including a couple right here in Sheboygan.
Our favorite is The Blind Horse Restaurant and Winery. Located in Kohler, Wisconsin (only 5 miles from the town of Sheboygan), this winery boasts a rustic interior with barrels of wine on display and an impressive gourmet food menu (filet mignon, anyone?).
They feature in-house blends like the Dam Sire, which mixes Syrah, Shiraz, and Cabernet Sauvignon into a playful mix of rich tobacco notes and jammy tints from the Shiraz.
Where to Stay in Sheboygan
Sheboygan is a cute little town to explore on a road trip away from Milwaukee. The good news is that we’ve got you covered with ample options for accommodations, including:
- Pine Dunes Cabin: A 4-bedroom cabin with a hot tub, wood stove, and gorgeous vistas of natural landscapes.
- Old Trees Farm: A 100-year-old historic home with nearby animals that produce fresh eggs for you to enjoy at breakfast!
- Uptown Coach House: A cozy, 2-bedroom spot in Downtown Sheboygan, walking distance from the beach and fully equipped with a smart TV, full bathtub, and comfortable furnishings for the family to enjoy.
Explore more places to stay in Sheboygan!
2. Elkhart Lake
Photo Credit: ajkelly
- Elkhart Lake, Rhine, WI
- Best for water activities and relaxing vibes
Technically part of Sheboygan County, Elkhart Lake is a village that’s about a half-hour drive from the town of Sheboygan. With a population of 1,000 or so, you really get the friendly community energy of a small town. Here, locals stop and say hello to you as you pass them by on a hiking trail or enjoy a succulent, smoked slab of meat at the Garage BBQ Pit.
The lake itself glimmers and inspires with its light-blue, translucent waters that welcome you for a swim, pontoon cruise, kayak, or other water activities.
And, if you want easy access to Elkhart Lake Beach? You can stay at our 7-bedroom Elkhart Lake lodge, spanning 5 acres of flat, Montana-esque plains and scenery. Enjoy cozy wooden accents and tastefully decorated interiors that can host up to 18 guests — perfect for a family reunion!
3. Indianapolis
Photo Credit: Mihai_Andritoiu
- Indianapolis, IN
- Best for: City slickers
Craving a getaway but don’t want to sacrifice the excitement of big-city Milwaukee? You might have visited Chicago, Illinois, one too many times, but luckily, you’re not too far from another metropolitan city that you can check out on a weekend getaway: Indianapolis, Indiana, aka Naptown, named after the city’s booming jazz scene from the roaring 20s.
You’ll need to drive four hours to get to Indianapolis, but if you leave early, that leaves plenty of time to explore attractions like:
- The Jazz Kitchen: Named a top jazz club in the world;
- Bottleworks District: Featuring endless local food options, a theater, and shopping boutiques.
- Indianapolis Motor Speedway Museum: Great for track tours to learn about the city’s rich racing history.
4. Green Bay
Photo Credit: KUROKAWA MOKU
- Green Bay, WI
- Best for amusement parks and a nice medium between small town and big city
Located within two hours driving from Mke, Green Bay is a mid-sized city that blends industry and agriculture with its history and tight-knit, small-town energy.
The Bay Beach Amusement Park attracts many traveling families to Green Bay — rollercoasters, anyone? While it’s temporarily closed, it should be open for the Spring/Summer season. Just make sure to check the website for more details.
Other attractions in Green Bay include:
- Wequiock Falls: Hiking trails are much more enjoyable with views of waterfalls, right? Located in Wequiock Falls County Park, this sight is a must-see on your Green Bay vacation for its tranquil scenery and Niagara Escarpment rock formation!
- Green Bay Botanical Garden: Walk through 147 acres of diverse plant life that spans over 120,000 different species of trees, flowers, and fungi. The Botanical Garden also features events like Hatha Yoga and family-friendly educational activities — just check their website for updates.
- Delilah’s: Foodies rejoice at Delilah’s, a local spot with farm-fresh meals and classic comfort foods like corn waffles, pork belly sandwiches, and Cajun shrimp po’boys.
5. Lake Geneva
Photo Credit: VinayPathak87
- Lake Geneva, WI
- Best for animal lovers and tranquil beaches
Under an hour South of Milwaukee sits the quaint town of Lake Geneva, Wisconsin. Here, you’ll find tons of opportunities to decompress, from beach activities and hiking to cultural attractions like museums and galleries.
Lake Geneva is a great spot to enjoy wildlife and animal interactions if you're traveling with kids. You can horseback ride through green pastures and ravines, check out local petting zoos, and even take a mini safari year-round to see some giraffes at Safari Lake Geneva.
Flat Iron Park is another great attraction that features live music in the Spring and Summer months, along with local food vendors with farm-fresh eats and comfort classics.
6. Wisconsin Dells
Photo Credit: Aaron of L.A. Photography
- Wisconsin Dells, WI
- Best for theme parks and nature
The best way to tire out a family of young children? A jam-packed day at a theme park, of course! Wisconsin Dells is home to a number of amusement parks and waterparks like:
- Mount Olympus: This massive theme park includes Greek god themed slides and pools that the kiddoes won’t get enough of. Enjoy rollercoasters, a rotating waterslide, and go-karts for those who want to stay dry!
- Tom Foolery’s Adventure Park: If you don’t feel like packing swimsuits and towels, the kids will still love an adventure at Tom Foolery’s for its rollercoasters, massive arcade, and laser tag activities!
Wisconsin Dells is also home to a number of natural wonders, including the Dells of the Wisconsin River State Natural Area. Here, you’ll find gentle streams and impressive sandstone rock formations within a scenic gorge.
7. Sturgeon Bay
Photo Credit: Dave Jonasen
- Sturgeon Bay, WI
- Best for fishing
Sturgeon Bay is a gem of a small town within Wisconsin’s Door County. With a population of just under 10,000 people, it’s an ideal weekend trip destination for couples or families that crave a more laid-back, nature-filled experience.
You’ll find abundant fishing charter opportunities for both warm- and freshwater fishing, with the potential to catch large fish species like Largemouth Bass and Walleye. This small town features a few boutique hotels to enjoy a cozy weekend getaway with a historic downtown area and many nature activities.
Don’t forget to visit Potawatomi Park, a bit north of Sturgeon Bay, where you can enjoy canoeing, kayaking, and beachside activities year-round. Just keep in mind that this park’s beaches don’t always have lifeguards, so you’ll need to keep a close eye on the kids.
Book Your Weekend Trip with Sheboygan Vacation Rentals!
Brew City (Milwaukee) is only a stone’s throw away from countless small towns, waterfalls, beaches, state parks, and diverse metropolitans to decompress from your hometown stresses and enjoy a truly relaxing or adventurous vacation.
From Sheboygan’s beaches and wineries to Elkhart Lake’s stunning natural landscapes, Wisconsin’s beauty has no limit.
But if you’re after a nice mix of history and relaxation, hear us out. The best way to enjoy the best of Wisconsin's small towns and cottage country is to put your trust in local experts like our team at Sheboygan Vacation Rentals.
As born-and-raised locals, we know the ins and outs of Sheboygan and nearby towns to help our guests make the most of their getaway.