10 Unforgettable Short Road Trips From Milwaukee, Wisconsin for Weekend Getaways

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10 Easy Road Trips Near Milwaukee, WI (That Take You Out of the County)

If you live in or are visiting Milwaukee, Wisconsin and you’re craving a quick change of scenery, you’re in luck. Within about an hour or two, you can find beaches, lighthouses, wineries, hiking trails, and even a few quirky small-town stops. The best part? Each of these road trips takes you out of Milwaukee County into nearby areas like Ozaukee, Racine, Washington, Waukesha in Wisconsin and Muskegon and Ottawa Counties in Michigan—perfect for a day trip or a relaxed weekend. Let’s hit the road.

1. Cedarburg, WI – Storybook Streets & Wine Tasting (Ozaukee County)

Just about 25–30 minutes north of Milwaukee, Cedarburg feels like stepping into a small-town movie set. If you’ve ever wished for a slow, cozy day with old brick buildings and little shops, this is it. Top things to do in Cedarburg:
  • Stroll Washington Avenue: Pop into boutiques, antique stores, and local art galleries lining the historic downtown.
  • Cedar Creek Settlement: Explore this restored 1860s mill turned shopping area. Don’t miss the Cedar Creek Winery for a tasting.
  • Grab a sweet treat: Try homemade fudge, ice cream, or a slice of classic Midwestern pie at one of the cafes or bakeries.
If you time your visit in fall, Cedarburg’s festivals—like the wine & harvest events—can turn a simple day trip into a yearly tradition.

2. Port Washington, WI – Lighthouse Views on Lake Michigan (Ozaukee County)

Keep heading north along the lake from Milwaukee and in under 40 minutes you’ll reach Port Washington, a charming harbor town with a New England feel right here in Wisconsin. Don’t miss:
  • Port Washington Breakwater Lighthouse: Walk out along the pier for classic Lake Michigan views and photos.
  • Downtown & Marina: Watch the fishing boats, grab a cup of coffee, and wander the small shops near the water.
  • Upper Lake Park: Pack a picnic and enjoy the bluff-top views over the lake. There’s plenty of green space for kids to run around.
It’s an easy half-day trip that can turn into a full day if you slow down and enjoy the lake breeze.

3. Harrington Beach State Park – Quiet Beaches & Starry Skies (Ozaukee County)

About 40–50 minutes north of Milwaukee, Harrington Beach State Park offers a peaceful stretch of Lake Michigan shoreline that often feels less crowded than other beaches. What to do there:
  • Walk the beach: The shoreline goes on for roughly a mile, perfect for a long, calm walk.
  • Explore Quarry Lake: A former stone quarry now filled with clear water and surrounded by easy walking trails.
  • Stargazing: On clear nights, this is a surprisingly good spot to see the stars, away from city lights.
Bring layers—the wind off the lake can feel cooler than it looks, even in summer.

4. Historic Downtown Racine & Lakefront – Art, Ice Cream, and a Lighthouse (Racine County)

Head about 35–45 minutes south of Milwaukee and you’ll reach Racine, another Lake Michigan city with its own flavor and history. Highlights in Racine:
  • Racine North Beach: A wide, sandy beach that’s great for swimming and sunbathing in summer.
  • Wind Point Lighthouse: One of the oldest and tallest lighthouses on the Great Lakes. You can walk the grounds and soak in the lake views.
  • Kringle tasting: Racine is famous for its Danish kringle. Stop by a local bakery and try this flaky, ring-shaped pastry. It makes a perfect road-trip snack.
If you like art and architecture, keep an eye out for Frank Lloyd Wright–designed buildings around the city.

5. River Bend Nature Center – Paddling & Nature Trails (Racine County)

If you want more nature near Racine, drive a few extra minutes inland to the River Bend Nature Center. It’s a calm spot for families or anyone wanting to unplug. Things to do:
  • Kayak or canoe the Root River: Rentals are often available in season, and the water is usually gentle enough for beginners.
  • Walk the trails: Short, easy paths wind through trees and along the river, good for all ages.
  • Watch for wildlife: Keep an eye out for birds, turtles, and the occasional deer.
This makes a nice pair with a quick stop in downtown Racine or on the lakefront.

6. Holy Hill – Scenic Views & Fall Colors (Washington County)

About 40–50 minutes northwest of Milwaukee, Holy Hill National Shrine of Mary sits high on a hill in Wisconsin’s Kettle Moraine landscape. You don’t have to be religious to appreciate the setting. The views alone are worth the drive. Why go:
  • Climb the observation tower: Get a sweeping 360-degree view of rolling hills, farms, and forests. In fall, the colors are incredible.
  • Walk the grounds: Peaceful paths and gardens offer a quiet place to slow down.
  • Scenic drive: The back roads around Holy Hill are perfect if you enjoy drives through the countryside.
If you like photography, this is one of the best spots near Milwaukee for wide, dramatic landscape shots.

7. Pike Lake & the Kettle Moraine – Hiking and Lakeside Picnics (Washington County)

Not far from Holy Hill, you’ll find Pike Lake Unit of Kettle Moraine State Forest, around 45–60 minutes from Milwaukee depending on your route. At Pike Lake you can:
  • Hike the trails: Choose from easy to moderate routes through forests and glacial hills.
  • Climb the observation tower: Similar to Holy Hill, this tower offers another great view of the area.
  • Relax by the water: There’s a swimming beach, picnic areas, and spots to simply sit and enjoy the lake.
Pair this with Holy Hill for a full day of nature, views, and quiet time.

8. Lake Country Breweries & Lakes – Oconomowoc & Delafield (Waukesha County)

About 35–45 minutes west of Milwaukee, Waukesha County’s “Lake Country” area—especially around Oconomowoc and Delafield—is perfect for a relaxed day of water views and local flavors. Ideas for your Lake Country road trip: On a summer day, Lake Country feels like a mini vacation without the long drive.

9. Lapham Peak – Hike to a Fire Tower View (Waukesha County)

Near Delafield, about 30–40 minutes from Milwaukee, Lapham Peak Unit of Kettle Moraine State Forest is one of the closest “big view” hikes from the city. What makes Lapham Peak special:
  • Fire tower lookout: A short uphill walk leads to a tall wooden tower with wide views of rolling hills and forests.
  • Trail options: Miles of trails for hiking, running, or cross-country skiing in winter.
  • Picnic spots: Plenty of shady tables to relax after your hike.
If you’ve been wanting to try hiking but don’t want anything too intense, this is a perfect starter spot.

10. Cross-Lake Adventure: Muskegon & Holland, MI (Muskegon & Ottawa Counties)

Want to really shake things up? Head across Lake Michigan to the beaches and dunes of western Michigan. You can either:
  • Drive around the south end of the lake (a longer trip, 3.5–4.5 hours depending on your route), or
  • Take the seasonal ferry from Milwaukee to Muskegon (when operating), which turns the journey itself into part of the fun.
Once you’re over in Muskegon County and Ottawa County, you can explore: In Muskegon:
  • Pere Marquette Beach: A wide sandy beach with views that honestly feel a bit like the ocean—just with fresh water.
  • Muskegon Lake: Marinas, walking paths, and easy photo spots along the water.
In Ottawa County (around Holland, MI):
  • Holland State Park: One of the most popular beaches on the Michigan side, with views of the famous red “Big Red” lighthouse.
  • Downtown Holland: Brick streets, cozy shops, and restaurants make it a fun place to wander.
This road (or ferry) trip is great if you’re ready for a full weekend getaway rather than just a single afternoon.

Tips for Planning Your Milwaukee Road Trips

  • Check drive times: Most of these spots are within about 30–60 minutes, but heading into Michigan can take longer or depend on ferry schedules.
  • Pack smart: Bring layers, snacks, water, and a small daypack. Lake Michigan weather can change quickly.
  • State park passes: Wisconsin state parks often require a vehicle admission sticker. It’s usually worth it if you plan to visit more than one.
  • Start early: You’ll beat the crowds at beaches, parks, and popular viewpoints.

Where Will You Go First?

From lighthouses and beaches to hiking towers and small-town streets, there are plenty of easy road trips near Milwaukee once you step outside Milwaukee County. Whether you’ve got a free afternoon or a full weekend, you can find something new without driving all day. Have you been to any of these spots—Cedarburg, Holy Hill, Port Washington, Racine, Lake Country, or over to Muskegon and Holland? Share your favorite nearby road trip from Milwaukee in the comments. And if you know someone who’s always saying, “We should get out of the city more,” send them this guide or share it on social media to help them plan their next adventure.
Location: Georgetown, IN, USA

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