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Five gorgeous fall family hikes near Milwaukee

Cooler temps equal one thing in my mind: GREAT HIKING WEATHER! Minimal mosquitoes, less overheating and complaining from my kids, and views of leaves changing colors are all selling points when I’m considering what to do with my week.

When I suggest hiking to my four kids, ages 5-10, they predictably chime in with protests of “But it’s SO boring!” and “It’s too hard!” So over my tenure of dragging them to do things I like to do (parenting), I’ve learned to call hiking “playing in the woods” because at the end of every single hike, my kids are begging for more and talking about their next adventure outside.

Gorgeous colors at Holy Hill

Below are quick reviews of my five favorite hikes to do with kids in the Milwaukee area. I’ve included some that are free of charge, some that are ADA accessible, some that are in the city, and some that require a drive. Before you go, remember these tips:

  • Have your kid(s) carry a backpack for their own water and hiking accessories like magnifying glasses, paper/pencil for drawing, binoculars etc.
  • Check the weather, wear sturdy shoes with socks, and bring extra clothes for afterward
  • PACK LOTS OF SNACKS with those water bottles, and carry out your garbage like a responsible citizen
  • Much like the parenting strategy “leave the park when they’re having fun so they’ll want to come back someday,” start with shorter and easier hikes at first. If your kids are left wanting more, they’ll be more excited the next time you plan a hike. 
Hide and Seek at Retzer Nature Center

Retzer Nature Center

This free center has both indoor and outdoor activities. It’s a 30 minute drive from the city, and a wonderful way to introduce hiking to your littles. The very short adventure trail is ADA accessible, with Braille and lettered signs highlighting native Wisconsin plants, birds and animals. Check out the trail map for lots of easy hikes through pines and prairies, and make sure to see what the nature center has to offer when you go (hint…there’s a planetarium!!). Bathrooms are available inside the nature center 8 a.m.-4:30 p.m. at S14W28167 Madison St. Waukesha, Wis., 53188.

Wehr Nature Center

Whitnall Park offers more than Boerner Botanical Gardens and a golf course; it’s home to Wehr Nature Center, too! This gem is part of Milwaukee County Parks and hosts flat trails, a wheelchair accessible boardwalk, a waterfall and much more. If you have more adventurous hikers, don’t worry because Wehr offers over three miles of trails in total. Admission is free, and there is a $3.50 parking fee for cars. Restrooms are open inside during building hours at 9701 W. College Ave. Franklin, Wis., 53132.

Scenic trees at Holy Hill

Holy Hill

This adventure is prime for viewing fall leaves, so to plan around peak colors visit Travel Wisconsin for a Fall Color Report. Then, fuel up for your hike at The Sawmill Inn just east of Holy Hill, and make sure to try the blueberry pancakes! While Holy Hill is a place of worship, it offers a spiritual connection to nature as well. This is a great opportunity to have a conversation with your family about how diverse our community is (both locally and globally), and the different religious and spiritual beliefs that surround us daily. The Scenic Tower has 178 steps to the top of an outstanding lookout, and remember that the top of the tower is open with large windows and may make some kids nervous. Also be aware that in rainy or very windy conditions, the tower may be closed so give the monastery a call at 262-638-2838 to confirm. In addition to the tower, Holy Hill has a paved path through the Stations of the Cross and links up to the Ice Age Trail, if you’re looking for a longer hike. Restrooms and parking are available at the base of The Basilica at 1525 Carmel Rd. Hubertus, Wis., 53033.  

Exploring abandoned factory remnants at Scuppernong Nature Trail 


The Scuppernong area in Dousman has quickly become my go-to spot because within a few miles there are three choices for great hikes. The Scuppernong Springs nature trail is about 1.5 miles long and meanders through natural springs, abandoned factory walls and outstanding prairie views. If you’re up for a more challenging hike among tall pines and hardwoods, head to the Scuppernong Trail System. The red loop is 2.3 miles of considerably hilly and gorgeous terrain, with the option of doing even longer hikes on the green and orange loops. I’m a sucker for shade and wind protection from towering trees, so this is one of my all time favorite hikes. Additionally, Paradise Springs is only a 10 minute drive from the Scuppernong trails, and is a half mile paved trail through an abandoned hotel/horsetrack/spring house. Check out the links for more history! You’ll need a daily or annual vehicle admission sticker for these locations, and vaulted toilets are available at the parking lot of the Scuppernong Trail System.

Lapham Peak observation tower

Lapham Peak

Only 30 minutes from Milwaukee is home to Lapham Peak, with trails for hiking, biking, skiing and more. You may know of the intermediate and advanced trails which have some elevation, but if you’re starting out with kids you should check out the Plantation Path. It’s just under two miles, is paved, and leads to the observation tower for some great fall color viewing. Enter off of Highway C in Delafield, with your previously mentioned vehicle admission sticker, and park at the Homestead Parking lot where restrooms are available. When you follow the signs for the Plantation Path, you’ll be led through a prairie restoration project, and eventually through a pine plantation. About halfway through the loop, a small path leads to the 45-foot observation tower with wonderful views of the area, even of Holy Hill in clear weather!