Best Bike Trails Near Milwaukee for Your Next Subaru Adventure

There’s something about summer in Wisconsin that makes you want to get outside. Maybe it’s a Saturday morning ride along Lake Michigan, an afternoon exploring a new trail with the family, or simply throwing the bikes on the car and seeing where the day takes you.

Fortunately, you don’t have to travel far from Milwaukee to find a great place to ride.

Southeastern Wisconsin has an impressive network of bike trails that can take you past the lakefront, through wooded parks, across quiet countryside, and into some of our favorite Wisconsin communities. And when you have a Subaru with room for bikes, helmets, water bottles, snacks, and everything else that comes along for the ride, planning a spontaneous summer adventure gets a whole lot easier.

If you’re looking for somewhere new to ride this summer, here are four Milwaukee-area trails worth adding to your list.

Start Close to Home on the Oak Leaf Trail

If you live around Milwaukee, you’ve probably crossed the Oak Leaf Trail countless times without realizing just how extensive it is.

The trail system covers more than 135 miles throughout Milwaukee County, with most sections paved and multiple routes giving you plenty of choices depending on how far you want to ride.

One of our favorite summer options is the Lake Park Loop. You can start near the Milwaukee Art Museum and ride along the lakefront past Veterans Park, McKinley Park, Bradford Beach, and Lake Park before reaching the North Point Lighthouse.

It’s the kind of ride that reminds you just how beautiful Milwaukee can be during the summer.

If you’d rather explore the south side, the South Shore Line takes riders through areas including Bay View, South Shore Park, Warnimont Park, Sheridan Park, and Grant Park.

The best part about the Oak Leaf Trail is that you don’t need to make an entire day of it. Pack up the bikes after breakfast, find a convenient trail access point, and you can be riding within minutes.

Spend a Day Exploring the Hank Aaron State Trail

For a ride that feels distinctly Milwaukee, try the Hank Aaron State Trail.

The approximately 12-mile trail connects Milwaukee’s lakefront with areas farther west and passes near some recognizable local destinations along the way. You can ride near Lakeshore State Park, Discovery World, the Milwaukee Art Museum, and toward the American Family Field area.

It also connects with the Oak Leaf Trail, so more experienced cyclists can combine routes and turn a relatively short outing into a much longer ride.

One thing to keep in mind if you’re planning a ride in 2026: portions of the Hank Aaron State Trail are affected by construction. The Wisconsin DNR reports that the River Loop is expected to remain closed through at least October 2026 because of the 16th Street Bridge replacement project. Check the Wisconsin DNR’s current trail conditions before heading out.

That’s a good habit for any Wisconsin biking trip, especially during road-construction season.

Head North for the Ozaukee Interurban Trail

Sometimes half the fun is getting out of town for the day.

Load the bikes into or onto your Subaru and head north from Milwaukee to the Ozaukee Interurban Trail. The paved trail stretches approximately 30 miles through Ozaukee County and connects communities including Mequon, Thiensville, Cedarburg, Grafton, Port Washington, and Belgium.

This ride has a completely different feel from Milwaukee’s urban trails.

You’ll encounter stretches of farmland, wooded areas, wetlands, waterways, and small communities along the route. Depending on where you start, you can plan a leisurely morning ride or make a full day of it.

One idea we particularly like is riding a section of the trail and then stopping in Cedarburg or Port Washington for lunch before heading home.

That’s our kind of Wisconsin summer day.

The trail is free to use, although it’s worth checking the Ozaukee Interurban Trail website before leaving because some portions are undergoing improvements and repaving during the 2026 season.

Make a Day Trip of the Glacial Drumlin State Trail

If you’re looking for a bigger adventure, point your Subaru toward Waukesha.

The Glacial Drumlin State Trail stretches approximately 52 miles from Waukesha to Cottage Grove, following an old railroad corridor through southeastern Wisconsin’s glacial landscape.

You certainly don’t have to ride all 52 miles.

Pick a section that works for your group, park, unload the bikes, and explore at your own pace. The trail passes through farmland and small Wisconsin communities and includes both asphalt and crushed-stone surfaces.

Because it’s a Wisconsin state trail, bicyclists age 16 and older need a state trail pass.

There is also construction affecting part of the trail between Deerfield and London during 2026, so check the Wisconsin DNR website for the latest trail conditions and detour information before your trip.

Your Subaru Can Be Part of the Adventure

Bike rides tend to involve more gear than you expect.

There are the bikes, of course. Then come helmets, water bottles, backpacks, sunscreen, snacks, a tire pump, maybe a cooler, and—if you’re bringing the kids—probably another dozen things you didn’t plan on packing.

That’s one reason Subaru vehicles fit so naturally into an active Wisconsin lifestyle.

A Subaru Outback gives you plenty of versatility for weekend adventures. The Forester combines passenger room with flexible cargo space, while the Crosstrek is a great option for drivers who want something compact enough for everyday Milwaukee driving but still capable of carrying outdoor gear.

For families who need even more room, the three-row Subaru Ascent gives you space for passengers and all the equipment that tends to come with them.

Depending on your Subaru and its equipment, compatible roof-mounted and hitch-mounted bike carriers can also make transporting bicycles easier while leaving the cargo area available for the rest of your gear.

A Few Things to Bring Before You Ride

Wisconsin weather can change quickly, so checking the forecast before you leave is always worthwhile. Bring enough water for everyone, sunscreen, helmets, a small tire repair kit or pump, and a charged phone.

For longer rides, throw some snacks and an extra layer of clothing into your Subaru too.

Most importantly, check the official website for whichever trail you’re visiting before you leave Milwaukee. Trail conditions, construction, closures, parking information, and rules can change throughout the summer.

Then all that’s left to do is pick a trail and start riding.

Frequently Asked Questions About Biking Near Milwaukee

What are the best bike trails near Milwaukee?

Some of the most popular options include the Oak Leaf Trail, Hank Aaron State Trail, Ozaukee Interurban Trail, and Glacial Drumlin State Trail. Together, they offer everything from Milwaukee lakefront rides to longer trips through southeastern Wisconsin.

Where can I bike along Lake Michigan in Milwaukee?

The Oak Leaf Trail offers several opportunities to ride near Lake Michigan. The Lake Park Loop passes destinations including Veterans Park, McKinley Park, Bradford Beach, Lake Park, and North Point Lighthouse.

Is there a bike trail near downtown Milwaukee?

Yes. The Hank Aaron State Trail and portions of the Oak Leaf Trail provide convenient biking opportunities around downtown and Milwaukee’s lakefront.

What is a good family-friendly bike trail in Milwaukee?

Several paved portions of the Oak Leaf Trail can work well for recreational family rides. Choose a distance and section appropriate for the youngest or least-experienced cyclist in your group, and check the route for street crossings before leaving.

Do I need a trail pass to bike near Milwaukee?

It depends on the trail. The Hank Aaron State Trail does not require a state trail pass, while bicyclists age 16 and older need a Wisconsin state trail pass for the Glacial Drumlin State Trail. Always check current trail requirements before visiting.

Can I transport bikes with a Subaru?

Yes. Depending on the Subaru model and equipment, compatible roof-mounted or hitch-mounted bicycle carriers can be used to transport bikes. Your Subaru retailer can help you determine which accessories are compatible with your particular vehicle.

Where Will Your Subaru Take You Next?

One of the best things about living in Milwaukee is that adventure doesn’t have to mean driving hundreds of miles away.

You could spend Saturday morning biking along Lake Michigan, head north toward Cedarburg for an afternoon ride, or pack up the Subaru and discover a completely new stretch of Wisconsin trail.

That’s what summer is all about—getting outside, trying somewhere new, and making the most of the beautiful places we have right here in Wisconsin.

And if your current vehicle doesn’t have enough room for the bikes, passengers, and gear that come along with your adventures, stop by Schlossmann Subaru City of Milwaukee. We’d be happy to help you explore the Outback, Forester, Crosstrek, Ascent, and the rest of the Subaru lineup to find the vehicle that fits where you want to go next.

Tags: destinations, Milwaukee, new subaru
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