The Run Down

We're hitting the road for a weekend trip to Wisconsin. It starts with a 2.5-hour drive to Madison, Wisconsin, which we're using as our home base for the weekend. After getting settled on day 1 of your trip, you'll drive less than an hour away for some serious hiking up a 500-foot bluff. After climbing over boulders and hiking through woods, you'll have a post-hike meal at a family-friendly winery built into a hillside vineyard. On day 2, you'll visit a deep cavern and indulge in classic Wisconsin fare.

1. Homebase @ Madison, WI

2. Hike @ Devil's Lake State Park

3. Post hike eats @ Wollersheim Winery

4. Visit @ Cave of the Mounds

5. Wisconsin eats @ Grumpy Troll

1. Madison, WI

We’re using Madison as our home base for this weekend trip. For those who haven’t been, here is a basic primer to help you figure out where you want to stay and hang out in the city.

Below is a map with three landmarks to get your bearings.

At the center is the Wisconsin Capital Building, the tallest building in the city and a helpful marker to look to if you get turned around. The main commercial center is along State Street. For a quieter neighborhood but still reasonably close to the action, head over to Williamson Street (aka Willy Street). A bit more about State and Willy Street is below.

State Street

This is the most commercial district in Madison. At one end of the street is the Capitol Building, and at the other end is the University of Wisconsin campus. In between is a half-mile stretch that, while gobbled up by a fair amount of big box stores, is still filled with plenty of local coffee shops, boutiques, bookstores, bars, and restaurants. If you want to be at the center of all the action, find a hotel or vacation rental nearby. 

Willy Street

Williamson Street, otherwise known as Willy Street among locals, has a history of being known as a funky, hippy neighborhood. “Keep Willy Street Weird” is a common catchphrase used by some locals if that gives you any indication of the vibe. This area is about a good 2 miles from State Street. It’s a mix of residential homes with an eclectic mix of shops and restaurants.

We opted to stay in this area because it was cheaper and close enough to State Street if we wanted to go down there.

2. Devil’s Lake State Park
(Day 1)

We’re onto the main event for this guide. About an hour north of Madison is Devil’s Lake State Park. It covers over 9,200 acres and has 29 miles of trails for you to explore. We’re only covering a small portion of that, but what we cover will take you atop a 500-foot bluff with some serious views of the lake and the valley below.

Here are some logistics notes.

– We started at Balanced Rock Trail, and the trailhead is located at the southern end of the park.

– There is a parking lot close to the trailhead. Non-residents need to pay a $16 fee to park.

– Cellphone service is very spotty. While you can randomly pick up a signal, it’s best not to expect service.

From the parking lot, you’re a quick walk to the trailhead. You’re going in the right direction if you hit these train tracks. Cross over them and follow the path to get to the start of the Balance Rock Trail. By the way, these train tracks double as a walking trail that follows along the lake’s eastern edge.

This is the starting point of the Balance Rock Trail. It’s rated as the most difficult trail to hike because it’s steep and you’re climbing up giant stone steps, which can sometimes be uneven.  The total length is around 1/2 mile, but it will take 20-30 minutes to go up.

We went with a two-year-old strapped in a hiking backpack. It was a challenging workout but doable.

Here’s a screenshot of a map to give you a sense of where we were and the route we took.  Once you get to the top of the Balanced Rock Trail, it connects to a network of different trails.

If you want to follow our route, then take the path highlighted in yellow, which hugs the edge of the bluffs and overlooks the valley below. At the end of the yellow highlighted section is the CCC trail. It’s your way down off the cliff and back to your car. Similar to the Balanced Rock Trail, it’s a steep and rocky climb down to the bottom.

If we were to do this again, there’s an alternative starting point that’s easier and gets you to the same views. You’ll need to start at the lake’s northern end at the East Bluff Trailhead and work your way south. You’re hiking a longer distance, but the path is flatter, and you won’t need to scale many giant boulders.

Back to our route, below is a picture of different groups scaling up Balanced Rock Trail. On warm weather days, the trail can get crowded with people coming up and down through the same narrow passages.

Once you get to the top of the bluff, the trail levels out, and all your hard work is rewarded with sweeping views of the valley.

By the way, here’s an action shot of the toddler carrier we used. It’s the Osprey Poco.

From the top of the bluff, head east and follow the trail along the edge of the cliffs. This particular area is a prime spot for climbers. These climbers carried up crash pads and found a corner spot along the trail to do some bouldering. Along the way, we also ran into groups of climbers scaling down the side of the bluffs. If you got older kids and want to add even more adventure, there are top-rope climbing guides that will take you out here and get you set up to rappel down the side. The youngest they’ve taken out was four years old.  If you want to keep going, we’ve only covered about 2 miles of the 29 miles of hiking inside this park. There are a whole series of interconnected trails that branch off from here. There’s also the west side of the lake with its network of hiking paths.

3. Wollersheim Winery & Distillery
(Day 1)

After a long day of hiking, we’re rewarding ourselves by sitting on the hillside of a family-friendly vineyard, drinking wine, and eating cheese.

About a 20-minute drive from Devil’s Lake, and on the way back to Madison, is a winery hidden off the side of a small two-lane highway. We didn’t have this as part of our original plan. We decided to take the scenic route back to Madison and just happened to catch the sign for this place as we drove by, and I’m glad we did. Here are a few things to note about this place.

– Winery and distillery open 12 – 5 pm daily (bistro closes at 4:30 pm)
– Family-friendly, kids were everywhere

From the highway, you’re just passing through farmland after farmland, and you wouldn’t expect much of anything around here. But when you pull onto the grounds of Wollersheim Winery, it opens up to a beautifully manicured estate with a distillery and winery for you to check out.

A walking path takes you to the winery initially constructed in 1840 by Agoston Haraszthy, a Hungarian nobleman who discovered this sloped land was well-suited for growing grapes. The Wollersheim family eventually bought it in 1972, and it remains in their care today.

The winery on the left and a small bistro on the right are pictured below. The winery is their retail space where you can pick up bottles of their wines and a selection of cheese, crackers, and other snacks to accompany your haul.

The bistro is a casual, order-at-the-counter kitchen with French and locally inspired fare on the menu, like flatbread, baguettes, and quiches. You can also order wine by the glass here too.

Their outdoor courtyard is built into the side of the sloped hill next to where they plant their grape vines. Tables are first come, first served, and you seat yourself.   

4. Cave of the Mounds
(Day 2)

On day 2 of this weekend getaway, we’ve got you driving about 40 minutes away to another Southern Wisconsin attraction. We’re at Cave of the Mounds, where you’ll go underground into a cave discovered in 1939. Here are some notes before you go.

– Cave tours are operated all year round
– Doesn’t matter what the weather is outside; the cave is always around 50 degrees
– Self-guided tours cost $22 (Ages 13+); $13(Ages 4-12); Free (3 and under)
– No strollers or carriers are allowed, so keep that in mind if you’ve got young children
Details here.

It takes about an hour to get you through the cave. You’ll criss-cross giant caverns, maneuver through narrow passages, and come across underground streams and learn how those shaped the caves.

5. Grumpy Troll
(Day 2)

At this point, getting a bite to eat is probably in store. We’re going “full-Wisconsin” for the next stop and have you visiting the Grumpy Troll Brew Pub, just a few minutes’ drive from the Cave of the Mounds, to indulge in some good ol’ Wisconsin fare.

There are two parts to the restaurant. They have a pizzeria upstairs or a full dinner menu on the ground level.

We went all-in on their main course offerings of prime rib, chicken biscuits and gravy, and cheese curds. This spread is basically Wisconsin in food form.