10 Unforgettable Short Road Trips from Greenfield, Wisconsin (Milwaukee County)

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10 Easy Out-of-County Road Trips Near Greenfield, Wisconsin

Looking for fun day trips near Greenfield, WI that get you out of Milwaukee County for a bit? Maybe you’ve done all your usual Greenfield and Milwaukee spots and you’re ready for something new, but still close to home. The good news: you don’t have to drive all day to feel like you’ve gone somewhere special. Within about 30 minutes to 2.5 hours, you’ll find beaches, lighthouses, breweries, small-town main streets, and even a giant pirate ship… and that’s just getting started. Below are 10 short road trips from Greenfield that take you into nearby counties in Wisconsin and across Lake Michigan into Michigan’s lakeshore counties. All are out of Milwaukee County, and all make great half-day or full-day adventures.

1. Cedarburg Charm: Historic Downtown & Covered Bridge (Ozaukee County, WI)

If you like Hallmark-style small towns, Cedarburg should be at the top of your list. It’s only about a 30–40 minute drive north from Greenfield but feels like you’ve stepped into another era. Walk down Washington Avenue and you’ll see old stone buildings, boutique shops, and cozy coffee spots. I still remember the first time I walked into the old mill building and could smell fresh chocolate from a nearby shop—it felt like childhood in one deep breath. Don’t miss:
  • Historic Downtown Cedarburg – Antique stores, art galleries, wine tasting rooms, and cute cafes.
  • Cedar Creek Settlement – Shops and a winery inside a restored 19th-century mill complex.
  • Cedarburg Covered Bridge Park – About 5 minutes north of downtown; one of the last original covered bridges in Wisconsin.
It’s an easy place to park once and just wander. If you’re a planner, aim for one of their festivals—like Strawberry Fest or Wine & Harvest Fest. Just expect bigger crowds and plan parking a bit earlier.

2. Port Washington: Lighthouses & Lake Views (Ozaukee County, WI)

Drive about 40–50 minutes northeast of Greenfield and you’ll hit Port Washington, a pretty harbor town right on Lake Michigan. The marina is the star of the show here. On a clear day, the blue water and fishing boats almost make you forget you’re still in Wisconsin. It’s one of those places where you can just sit on a bench and zone out—in the best way. Highlights:
  • Port Washington Lighthouse – Walk out along the breakwater for great photos. Wear good shoes; it can be uneven.
  • Downtown Port Washington – Small but charming, with pubs, sandwich spots, and ice cream shops.
  • Upper Lake Park – Grassy bluff with lake views, playground, and picnic spots.
If you like fishing, consider a charter on Lake Michigan. If not, just enjoy fish fry at one of the local restaurants and call it a day.

3. Harrington Beach State Park: Quiet Beach Day (Ozaukee County, WI)

Want a beach without driving all the way to Door County? Harrington Beach State Park sits along Lake Michigan in northern Ozaukee County, roughly an hour from Greenfield. This is where you go when you need a calm, simple day outdoors: walk, sit, listen to the waves, repeat. What to do:
  • Walk the beach – It’s rocky in spots, sandy in others. Bring sturdy sandals.
  • Explore the quarry lake – Easy walking trail around a quiet inland lake.
  • Stargazing – On clear nights, it can get wonderfully dark out there.
You’ll need a Wisconsin state park pass or a daily admission. Pack snacks, water, and maybe a light jacket—the lake breeze can feel cooler than it looks, even in summer.

4. Historic Downtown Waukesha: Art, Murals & Riverwalk (Waukesha County, WI)

Head about 25–30 minutes west from Greenfield and you can be in downtown Waukesha, a walkable, artsy little city. It’s a fun pick if you want something different from Milwaukee’s big-city feel but still want restaurants, coffee shops, and nightlife all in one area. Top picks:
  • Waukesha Riverwalk – Easy, flat path by the Fox River; good for a casual stroll.
  • Public art & murals – Colorful walls and sculptures scattered around downtown. Great for photo walks.
  • Friday Night events (seasonal) – Car shows, music, and more during warmer months.
Grab a coffee, do the Riverwalk loop, then wander side streets to see what you find. It’s one of those downtowns where it’s fun to get “lost” for a bit.

5. Lakefront Fun in Oconomowoc (Waukesha County, WI)

About 45–50 minutes west of Greenfield, Oconomowoc sits right in the middle of “Lake Country” in Waukesha County. If you like water views, this is your stop. The town wraps around a string of lakes, with parks and paths that keep you close to the water. What to check out:
  • Downtown Oconomowoc – Shops, restaurants, and a laid-back small-town vibe.
  • Fowler Lake & Lac La Belle – Walking paths, boat watching, and spots to just sit and relax.
  • Village Green – Lakefront park that often hosts concerts and events in summer.
On a sunny day, grab a coffee or ice cream and walk the waterfront. In the evening, the lights reflecting on the lake make it feel surprisingly romantic for such a small town.

6. Washington County: Holy Hill Scenic Drive (Washington County, WI)

If you enjoy long views and rolling hills, take a road trip about 45–60 minutes northwest to Holy Hill in Washington County. Even before you get there, the drive itself feels like a break from city life. The main draw is the basilica perched on a hilltop. You can see its twin spires from miles away. Why go:
  • Climb the tower (seasonal) – On clear days, you can see for miles in every direction.
  • Scenic drives – Country roads, farms, and trees that really pop in fall.
  • Peaceful walking paths – Even if you’re not religious, it’s a quiet place to slow down.
If you time it for autumn, the fall colors can be some of the best in southeast Wisconsin. Just bring a light jacket; it can be windy at the top.

7. West Bend & the Milwaukee Riverfront (Washington County, WI)

Another Washington County option is West Bend, about 45 minutes to an hour from Greenfield. It’s an easygoing river town that makes a nice, low-pressure day trip. Things to do:
  • Downtown West Bend – Restaurants, local bars, and small shops with a friendly, local feel.
  • Riverwalk – Simple, scenic paths along the Milwaukee River.
  • Seasonal farmers market – One of the larger markets in the region (check dates before you go).
If you like combining a walk, a meal, and a bit of browsing, West Bend checks all those boxes without feeling crowded.

8. Racine’s North Beach & Lakefront (Racine County, WI)

Ready for another lakeshore option? About 40–45 minutes south of Greenfield is Racine, home to one of Wisconsin’s most popular city beaches. North Beach is big, sandy, and easy to spend a whole afternoon on. When the sun’s out and the water’s calm, it almost feels like you’ve slipped away to a small coastal town. Plan to:
  • Relax at North Beach – Swim, sunbathe, or walk the shoreline.
  • Walk the Lake Michigan Pathway – Paved lakefront path good for walking or biking.
  • Try a Racine kringle – This is kringle country. Hunt down a local bakery and bring some home.
If you like pairing beach time with food, Racine works well: hit the sand, then head into town for dinner before driving back to Greenfield.

9. Muskegon, Michigan: Big Dunes & Beach Day Trip (Muskegon County, MI)

If you’re up for a slightly longer adventure, head east across Lake Michigan’s shoreline into Muskegon County, Michigan. It’s about a 2.5–3 hour drive from Greenfield, depending on your route and traffic. Muskegon is a classic Great Lakes beach town, with dunes, lighthouses, and a relaxed, vacation feel. Main attractions:
  • Pere Marquette Park – Wide sandy beach with clear Lake Michigan water and great sunset views.
  • Muskegon South Pierhead Light – Another lighthouse to check off your list.
  • Dune areas nearby – Short drives to trails and overlooks for a bit of hiking and climbing.
If you leave Greenfield in the morning, you can still make it a very long day trip, but it’s even better as an overnight if you have the time. Either way, you’ll feel like you left your normal routine way behind.

10. Grand Haven, Michigan: Boardwalks & a Famous Pier (Ottawa County, MI)

Just south of Muskegon, in Ottawa County, Michigan, you’ll find Grand Haven—another big favorite on the Lake Michigan shore. Think of it as a classic summer beach town, complete with a long pier and red lighthouse. From Greenfield, you’re looking at around a 2.5–3 hour drive. It’s totally doable as a long day trip if you start early and don’t mind getting home late. What makes it special:
  • Grand Haven State Park – Beach, dunes, and a huge stretch of sand.
  • Boardwalk – Paved path along the channel with shops, food stands, and great people-watching.
  • Grand Haven Lighthouse & Pier – One of the most photographed spots on the Michigan shore.
If you can stick around until evening, the sunsets here can be incredible. Watching the sky turn orange and pink over the lake is one of those simple moments you remember long after the drive home.

Tips for Planning Your Road Trips from Greenfield

To make these short road trips from Greenfield, WI even smoother, keep a few basics in mind:
  • Check drive times – Google Maps is your friend, especially for Michigan trips.
  • Watch the weather – Lake Michigan can change conditions quickly. Bring layers.
  • State park passes – Wisconsin and Michigan parks may require daily or annual passes.
  • Pack a small “go bag” – Water, snacks, sunscreen, phone charger, and a light jacket go a long way.
Even a simple half-day drive can reset your mood. Sometimes just seeing a new skyline, shoreline, or small-town main street is enough to feel like you’ve gone on vacation—without the airport stress.

Where Will You Go Next?

From Ozaukee County’s lighthouses to Waukesha County’s lakes and all the way over to Muskegon and Grand Haven in Michigan, you’ve got a full list of easy getaways just a short drive from Greenfield. Which of these road trips would you try first? Are you a beach person, a small-town shopper, or more of a scenic-drive-and-photo-stop type? Share your thoughts in the comments—and if you’ve discovered another great out-of-county day trip from Greenfield, I’d love to hear about it. If you found this guide helpful, please share it with friends or family who are also looking for new things to do near Greenfield, Wisconsin. Your next favorite spot might be just an hour down the road.
Location: Georgetown, IN, USA

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