2,800-Mile Wedding Road Trip

My best friend Matt was getting married and I was part of the wedding party. He lives on a large parcel of hunting and farming land in rural Wisconsin, a perfect venue for the wedding. I decided to skip flying and renting a car and instead make it a road trip. One thing lead to another, and I found myself reviewing a loose itinerary covering 16 days over the month of October. There were only two solid commitments throughout the whole timeline. I needed one specific day to be on the computer with reliable internet for some critical meetings, and I needed to be present and on time for wedding related events. Easy.

The first half of the plan was pretty low key.

  • Day 1-2: Drive From Denver to Chicago.
  • Days 3-5: I wanted to ride my former local mountain bike trail systems. Palos and Kettle Moraine State Forest were my old stomping grounds. I was also hoping for my first real ride at Raceway Woods.
  • Day 6: I had some important things scheduled. I was going to be stuck on the computer in meetings all day, during which my mom was going to pick up Morgan from the airport. She was flying in to join me for the remainder of the trip.
  • Day 7-8: Wedding related activities.

The second half of the plan was when the adventure would really begin.

  • Day 9: Leave Wisconsin in the morning, a quick stop in Minnesota and continue on to a camping reservation in South Dakota.
  • Days 10-15: Anything we wanted. No set route and no schedule, just a general plan of heading West. We hoped to check out a yet-to-be-determined combination of Badlands, Black Hills, Yellowstone, Grand Tetons, and/or Bridger-Teton. We’d play it by ear, going as fast or as slow as we wanted, and see where we ended up.
  • Day 16: Arrive back home in Colorado.

Adventure doesn’t follow a script, and despite quite a bit of the plan going out the window this 8 state trip had state parks, national parks, hiking, mountain biking, weaponized nukes, caves, mountains, national forests, a palace, an epic campsite along a river bank, ghost towns, the craziest store we’ve ever happened across and even a Transformer.



Day 1-2: With the 4Runner loaded up I topped off the tank and hit the road, pointed East.

I drove through Colorado and Nebraska and spent a quick overnight at the Prairie Rose State Park just across the Iowa border. In the morning I stopped for breakfast at Railroad Bill’s Dining Car in Des Moines.

It was fantastic!

Continuing East, nothing happened–welcome to the Midwest. Denver to Chicago is 1,000 miles of straight, flat highway lined by nothing except Iowa’s one pride and joy.

Ladies and gentlemen, I present to you, Iowa 80! The “World’s Largest Truck Stop”.

Approximately 4,986 hours into the trip I finally made it to Chicago.



Day 3: A lot of unexpecteds started to come into play. First – At my sister’s house, my nephew was sick fighting a cold. Second – My next stop was going to be my mom’s house and her husband was undergoing chemo treatments. I couldn’t bring a cold with me. Third – Heavy rain was putting all my hopes of riding dirt in jeopardy.

After considering my options I made a new plan. Raceway Woods got hammered with rain and was out of the question. I was really disappointed by that because when I moved from Chicago in 2012, we (CAMBr – Chicago Area Mountain Bikers, a 501c-3 nonprofit of volunteers that builds and maintains natural surface singletrack trails) had just finished the Raceway Woods clean-up and had cut the first 1-mile loop of trail. It was a successful proof of concept for the county and landowners. The site, a long-forgotten but historic 1/4 mile oval racetrack in the woods, tucked away on the outskirts of Chicago, got a new lease on life. The trail system has grown and expanded over the years, and it is now roughly 6 miles of singletrack looping through the trees. I was excited at the prospect of finally seeing that trail system come to fruition, so I was really disappointed when the rain canceled my plans, especially knowing I may not get another chance to come back. Palos was also doubtful. It had rained in the area most of the night, but checking the playback of the radar pattern, it looked like there was a hole in the storm system that may have spared the trails.

The new plan was to make the trek to Palos, hopefully ride, then head North to my mom’s in Wisconsin from there. When I arrived I was not disappointed!

The rain had in fact come, but the storm dropped just the right amount of moisture. The air was crisp, and the dirt was just wet enough to be slightly tacky, providing extra grip, but dry enough to remain fast rolling. This ideal combination is known as “Hero Dirt”.

It was time to let the Devinci stretch its legs.

The trails here aren’t very technical, but they are fast, flowy, and fun.

As you can imaging, Chicago is not a very mountain-bike-friendly city. This trail system is a hidden gem surrounded by endless concrete. The only reason it exists today, is because of its dark past buried below this gravestone.

This location was the start of the US nuclear program and the Manhattan Project itself.

While recreation here has been deemed “safe”, this land will never be dug up or developed. As such, this impressive network of urban area trails lives on.

It was a fantastic day. My expectations were surpassed and my highest hopes exceeded. After a few hours of riding it was time to load up and leave Illinois in the rear view mirror.



Day 5: It was time to hit the dirt again. The John Muir Trails at the Southern Unit of the Kettle Moraine State Forest will always hold a special place in my heart. For years I had been waiting for an opportunity to get back there and ride them again. That opportunity finally arrived, and as an added bonus, Matt was going to take a break from wedding prep to join me for a ride. Under threat of severe bodily harm, I promised his fiancée we would take it easy and I’d bring him back in one piece. I couldn’t let it be a repeat of Ray’s Indoor Mountain Bike Park.

This was the last time I took him mountain biking.

We met at the trailhead. After we spent a little time making fun of each other and hugging it out, we hit the dirt.

It was a beautiful day with trail conditions to match.

I couldn’t help but laugh to myself as I effortlessly strolled up the big “climb”. I use to mentally prepare myself leading up to it. A long climb used to last a minute, maybe two. I have since grown accustomed to Colorado, where one of my favorite trails starts with 7 continuous miles of uphill. But there is something to be said for “easy” flowy trails. Being able to zone out and just enjoy the ride from time to time is good for the soul.

At 6,000 feet closer to sea level than normal, I felt like I had a 3rd lung but Matt was getting tired. When fatigue starts setting in, your skill starts to go out the window and you get sloppy. With his wedding a couple days away Matt intelligently opted to wait back at the trailhead while I did one final loop at an all-out, as-fast-as-I-could, full-on sprint pace. It felt great.

I arrived back in the lot to find Matt laying under the 4Runner relaxing in the shade.

We grabbed some lunch and went our separate ways. Tomorrow was going to be my day of meetings and Morgan’s arrival. She had officially accepted a job offer after I had already departed on this trip so I knew we would need to celebrate. Finding a good bottle of bubbles in this small town proved difficult, but I was eventually successful. I also found some giant fuzzy socks with grippies on the bottom. I knew she would love them, so I grabbed those as well and continued back to my mom’s house.



Day 7: Morgan, in her new giant fuzzy socks with grippies, baked gluten free cookies with my mom.

Then we had a project to tackle. A few months prior, I went in on an order from RCI with Matt. He handed off my new fuel tank skid plate when we met to go riding. Not wanting to haul it around in the back seat for the next week, Morgan, with some guidance, installed it.

The old one was stamped from thin steel.

The new one was made from the same 1/4″ thick aluminum plating that armored the rest of the underside of the 4Runner.

With the new one in place, the threat of puncturing the plastic fuel tank offroad was all but eliminated.

With the 4Runner buttoned up and packed up, we walked down to the lake and took the boat out for a spin before heading out.



Day 8: Wedding Day!

We got up in the morning. Actually that’s a lie, I got up in the morning, Morgan did this…

I couldn’t help but notice how out of place the 4Runner looked in the hotel lot.

We eventually got ready and made our way over to the property. While I partook in the wedding party activities, Morgan fell in love with Matt’s horse, Remington.

Remmy was giving me that “Yeah, you know your jealous” look.

It ended up being a perfect Fall day for a wedding.

The event had such a low-key, fun vibe, as demonstrated by Morgan in the background. It was great catching up with old friends.



Day 9: We loaded up the 4Runner in the morning and made our way back over to Matt and Mallory’s to give our hugs and say our final goodbyes before heading North towards Minnesota.

The fastest route takes you right through The Wisconsin Dells via back roads. This town was such a staple for me growing up. Matt’s family has a cabin on the lake near his current property. We spent our summers there and trips to the Dells for dinner were commonplace. Morgan had never been, so we had to stop on our way through.

Our first stop was to “Have a Swig with Nig” at the historic Nig’s Bar.

Yeah, I know… It was named after the owner Nigel when it opened in 1947. Clearly the name has aged pretty poorly. But 75 years later it remains a popular no frills dive bar with a daily $1 shot special. It must have been 12-15 years since I had last stopped in for a swig with Nig. It was fun to be back.

Morgan found humor in the idea of getting a tattoo airbrushed onto her bicep before lunch with her mom.

We hoped to hit a roller coaster but they were closed for the season. The high ropes course and zipline were approximately 4 million dollars, so we passed on those. We settled on “Top Secret”, a long-standing fun house located inside an upside down White House.

Our favorite part was the giant Transformer out front.

We continued on to Minnesota for a nice meal with Morgan’s mom and then turned West towards South Dakota. We arrived at our campsite in the Palisades State Park and called it a night.



Day 10: We woke to a beautiful morning.

Fresh coffee in hand, we explored around our site a little bit.

We ate a quick, easy breakfast and packed up.

We made our way over to a trailhead parking lot in the state park and went for a hike.

It was a cool cliff-edge trail overlooking the water.

Upon completion of our hike we continued West. After what must have been 15-20 billboards advertising it, we made a detour for what we expected to be a ridiculous roadside attraction: The “World’s Only Corn Palace”.

To our surprise, it was just a big event center in the middle of town, but with the exterior covered in art made from corn cobs. And it was closed.

We had made the stop, so we pretended to love it anyway.

After refueling ourselves and the 4Runner we got back on the road. The angle of the sun made for some pretty cool shadows on the country highways.

We found ourselves off the beaten path.

With the sun starting to set, finding camp became a priority.

This will do nicely!

Quick tip — we open the sunroof and use our phone’s bubble level on the bottom of the tent floor to ensure the sleeping surface is nice and level.

We loved the view out the door of the tent.

Beautiful girl, beautiful river, beautiful sky and a beautiful sunset.

We had the gluten free chocolate chip cookies Mom had packed for us, which paired nicely with the celebration bubbles as we watched the sun go down.



Day 11: We were greeted by another lovely morning.

I couldn’t get over how great this spot was.

We performed our morning caffeine ritual.

Then we climbed down to the river bank for a closer look.

After that, we packed up and took the trail back out.

We stopped at LaFramboise Island Nature Area for a quick hike around the island.

We did some brief sightseeing in Pierre, the capital of South Dakota, before getting back on the road.

We stuck to the roads less travelled as much as possible.

We came across this sign and decided we had to check it out.

We followed the barely visible tracks to the GPS point.

In hindsight, maybe we should have just skipped seeing this historically significant location in an empty field…

South Dakota was proving to be a bit of a letdown. The Palisades State Park was worth visiting for a morning, the very hyped Corn Palace was a complete waste of time, and this empty field was just an empty field. And now the weather was starting to turn.

We continued West, and as we did the weather worsened.

Finally, Badlands National Park!

The terrain was otherworldly.

The moisture from the rain turned the clay-like landscape into a slippery mess that clung to your shoes like concrete. It wasn’t hard to imagine why the Lakota people referred to this region as bad lands.

It was stunning.

We continued around the park, getting out for short hikes along boardwalks and scenic overlooks during the breaks in the rain/sleet/hail.

The weather continued to worsen. The wind was gusting like crazy and the rain was like a sideways power washer. The weather forecast looked pretty terrible.

Common sense dictated that camping wasn’t in the cards. We found a local motel in Wall for the night and went looking for dinner. One thing we hadn’t anticipated is that after labor day most of this area shuts down for the season. There were surprisingly few options available to us. The one Mexican restaurant was our only option for anything gluten free. On the bright side, Mexican food is hard to mess up. Unfortunately, they did.



Day 12: After packing up and checking out, the first stop was the “World Famous” Wall Drug. This is the most advertised place in the state of South Dakota. What started as the local drug store in the town of Wall has grown into a really weird 76,000 square foot indoor strip mall thing that’s all under one roof. A busy day during the peak season can bring up to 20,000 visitors. It was certainly unique, but it wasn’t for us.

Photo from themerica.org

Yeah… pretty awesome. We made our way back into the Badlands with the intention of passing through and heading to the Black Hills National Forest. The terrain was still beautiful, the weather was still not.

We did as much travelling as we could, sticking to remote backroads.

Ghost towns are always fun to check out.

Note how clean the 4Runner looks–that was about to change. We found ourselves at a crossroad. We could T off and spend an hour and a half driving down and around the Indian Preserve on paved roads, or we could take the legal but unmaintained mud road a couple miles to drive straight across the reservation. As we always do, we chose the adventure of the unknown over a safe, time wasting detour. The road was groomed into a washboard and reasonably well maintained for the first few miles. As we crested a hill we stopped to reevaluate. The grooming ended as a gravel surface turned to muddy clay down a hill into a valley of shallow standing water over the road. It was remote, it was sketchy, and it was Indian land. If this didn’t go right, there was no getting help. The literal crossroad had turned into a proverbial one. Do we risk it, or do we backtrack and then detour? Morgan and I deliberated for a few minutes. In the end, nobody has ever had a good story to tell that started with “We didn’t want to risk it so we turned around to be safe”.

With the traction control off and the 4Runner locked up in 4WD, we drove down the slippery hill trying to carry some speed into the slop. The deep clay-like mud tried its best to bog the 4Runner down. With the throttle pedal to the floor to keep forward momentum, the 4Runner was all over the road. All four tires shot up rooster tails of mud. I had to constantly counter-steer to keep it on the road and pointing in the right direction. It was tense but we made it through the valley. Just one slick uphill left. All four tires continued to spin as we climbed the hill. The 4Runner was losing speed and we knew full well that if we lost all the momentum and came to a stop, we were going to be dead in the water. We closed in on the top as we continued to slow down. The speedometer was racing but we couldn’t have actually been moving much more than a snail’s pace as we crested the hill and got back to flat. If that uphill was another 30 feet, I don’t think we would have made it. Our racing heart beats calmed, smiles and laughter took over and the road turned back to a graded, maintained surface.

Notice the mud splatter on top of the hood.

We made it back to the first signs of civilization we had seen in hours.

Well, kind of.

We did find a place that looked interesting, and we decided to stop for a drink and check it out.

And interesting it was!

The 4Runner had gained quite a bit of weight during our little adventure.

The next stop was Wind Cave National Park, where we arrived 10 minutes too late for the final cave tour of the day.

We continued North to Custer State Park and hiked around a little bit.

While the snow missed us at the Badlands, we found it in the Black Hills.

We did some exploring.

With overnight temperatures expected to plummet into the 20’s, we found the only campground in the region still “open” that would give us a tent site with an electrical hookup so we could run the emergency space heater for the night.

The real feel temperature dropped into the teens overnight.



Day 13:

Hot coffee on an ice cold morning really hit the spot.

We got out of camp and spent the morning exploring more of the Black Hills.

We found ourselves at Mount Rushmore. Unfortunately our yearly National Park Pass did not cover admission and the price seemed excessively high to see man-made faces of former US Presidents carved into the rock. We looked from the truck. Unfortunately there wasn’t a vantagepoint from the road to be able to see the Crazy Horse Memorial, the Native response to Mount Rushmore.

We continued on through Keystone and into Rapid City for a late brunch. Then we spent too much money in the extra high pressure carwash bay removing what must have been a couple hundred pounds of mud.

The forecast continued showing overnight temps in the teens and more snow on the way for the northern part of the country, so that ruled out the idea of heading to Yellowstone. We decided we’d head towards home and see where we ended up. We went back to Wind Cave National Park for the tour we just missed yesterday. We rolled in, excited to go in the cave and see some of the 157 miles of documented, explored underground caves, with more yet to be discovered. We had the ultimate facepalm moment when we realized we both thought we were an hour earlier than yesterday, but arrived at exactly the same time and missed the last tour again.

The sunset looked like a scene from War of the Worlds.

With the wind wiping and the temps plummeting we made the tough call to drive straight through back to Denver and wrap up the trip 3 days earlier than planned. We were 2 weeks into the trip and just weren’t up to the idea of camping through some unseasonably brutal weather that we hadn’t prepared for.



Day 14: Hot showers and snuggling up in our own bed was very welcomed, but we hadn’t planned on being back yet and our minds were still in adventure mode. A morning bike ride was followed by lunch in the sun at the archery range, and a late afternoon hike.

Fun fact — Morgan is a certified archery instructor, and Lady Hawkeye was out there splitting arrows!

As the day drew to an end, we officially closed the book on this trip.

That evening we checked out the 2 National Parks we had seen on the trip in the book “Subpar Parks – America’s Most Extraordinary National Parks and Their Least Impressed Visitors”.



When all was said and done, we ended up making our way through Prairie Rose State Park, Palos Trails in the Maple Lake East, Pulaski Woods, Wolf Road Woods and Red Gate Woods Forest Preserves, John Muir Trails in the Southern Unit of the Kettle Moraine State Forest, Palisades State Park, LaFramboise Island Nature Area, Fort Pierre National Grassland, Badlands National Park, Pine Ridge Reservation, Buffalo Gap National Grassland, Black Hills National Forest, Wind Cave National Park, Custer State Park, Black Elk Wilderness, Mount Rushmore National Monument, Thunder Basin National Grassland, and Glendo State Park before heading back home and continuing the adventure locally.


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