A winter road trip to Janesville, Wisconsin

With a ho! ho! here, and some snow snow there, I headed to Janesville, Wisconsin for some holiday cheer and Midwestern charm. While summer might be the most popular time of year to take a road trip, winter in the Midwest showcases a snow-filled experience that certainly put me in the holiday spirit.

Church in Janesville, WI by MikesRoadTrip.com

Each time I plan a road trip I have a destination in mind, but never a route. After landing in Milwaukee and picking up my rental car, I noticed I had three options to Janesville. One was via Interstate 43, so that was out (I try never to drive the Interstate unless I just need to get from point A to point B quickly). I ended up picking the route in the middle, a short drive on I-94 then veering off to highway 67, south to Janesville. It’s not a very long drive, maybe 1.5 hours, but it took me about 2.5 hours with a few stops along the way. As I drove south I passed several farms, one with a silo and a large red barn that I really wanted to photograph, but found no place to pull over. The blanket of fresh white snow in the fields really made the red structure pop against the mostly blue sky.

By taking highway 67 I drove straight into downtown Janesville, avoiding the less attractive entrance to the city off I-90, which is essentially a big box district speckled with chain hotels. The downtown area however is utterly charming with many historic buildings and some fantastically large and opulent homes dating back to the mid-to-late 1800s. One of those homes was where I would stay for the first couple of nights, the Guardian Angel Bed and Breakfast.

When I drove up, I was impressed by the stately manor, which was surrounded by an expansive estate. The Italianate mansion was quite remarkable, but what really impressed me was how elaborately decorated the home was for the holidays.

Guardian Angel Bed and Breakfast in Janesville, WI by MikesRoadTrip.com

Carol, the owner/innkeeper, was telling me that she has five rooms in the basement, each dedicated for different holiday decorations. For Christmas, there were trees, lights, ornaments, Santa animations that sing when you walk by, and other Christmas decorations throughout the house. Not only in the living areas, but in the guest rooms as well, everywhere I turned there was holiday cheer.

Guardian Angle Bed and breakfast at Christmas in Janesville by MikesRoadTrip.com

While there was some snow on the ground from an earlier snowfall, my hope was to get dumped on. Over the next couple of days a bit of snow fell off and on, with a mix of sunshine that made for some nice photos, but my desire was to see Janesville blanketed in the white stuff. My wish came true a couple of days later during the early evening hours. I went to a dinner theater at a venue called the Armory, to see a holiday performance of Elvis when the snow had started to fall. By the time I left a couple hours later, five inches must have accumulated. I was as giddy as a kid on Christmas day. The white stuff was everywhere! It was quiet, as if the snowflakes were insulating any nearby city sounds. I loved the way the large fluffy flakes floated past the illuminating beams of the streetlights, accentuating the detail of each ice crystal as it made its way to the ground.

The Janesville Armory by MikesRoadTrip.com

My car was absolutely covered in snow. Thankfully, the rental company left a brush and scraper for me. I took great joy in sweeping the fresh snow from the windows and the hood of the car. My shoes made a squishy sound as the weight of my body compressed the snow beneath my feet. I know this is a laborious task for those who live year-round in these conditions, but for someone from the desert, this was a novelty that I thoroughly enjoyed. This seemingly simplistic experience I had is one of the joys of travel for me. What is mundane for some, is enthrallment for others.

Downtown Janesville during snow storm by MikesRoadTrip.com

Travelers like me see the world with fresher eyes than those of the local. Earlier this year I was road tripping around central Newfoundland when the road ended at a ferry terminal. I thought, “Why not see where it goes.” I drove aboard and disembarked just five minutes later on an island of just over 100 inhabitants. I stopped by the most awe-inspiring sight and was taking some photos when a local walked up to me and said, “Whatcha taking a picture of?” “This stunning scenery,” I exclaimed! He said, “If you say so.”

Central Newfoundland bay by MikesRoadTrip.com

To me, the ensconced body of water surrounded by small mountain bluffs with fishing vessels and a cloudless blue sky was a scene straight out of a movie. To the local, it was something he witnessed everyday of his life for the past 60 years. Perspective is an interesting state of mind.

For those who live in or near Janesville, they may not appreciate what they have like a visitors does. It seems to me that Janesville is one of those up-and-coming cities going through some revitalization, especially in the downtown area. This downtown urban interest is not unique to Janesville as I see it happening across the country. There is renewed interest in being close to the center of a city. From my experience, the one constant that spurs interest to an area and its eventual economic development (which is often overlooked by leaders), is the pivotal role the arts play. It’s great to see places like Raven’s Wish Gallery and Voigt’s Music Center fostering local artists.

During my visit to Janesville

…I drove around exploring the area. I found myself on highway 26 heading north when I ran across the small town of Milton. Just on the outskirts of town I saw a cemetery, so I went in to take a look. Don’t ask me why, but I have some sort of fascination with old cemeteries. Perhaps it’s the opulent headstones, or the peacefulness of those at rest, or even the stories that some of the headstones tell about the people who once roamed the earth.

Milton Cemetery by MikesRoadTrip.com

After taking a few photos I headed back to the center of town where I took a tour of the Milton House, which opened in 1844 as a stagecoach inn by the founder of the town, Joseph Goodrich. In 1948 the Milton Historical Society was formed to preserve Milton’s history. One of the highlights of the museum for me was the tunnel that was used to help fugitive slaves traveling the Underground Railroad escape to freedom. When you experience sites like this it really puts history into perspective. I don’t know about you, but the older I get, the more fascinating history becomes. I think it could have something to do with the fact that when we are young, we have little history to draw from, but as we age, we become a part of history. (Click the following link to view my photos from the Milton House Museum).

Milton House aerial photo by MikesRoadTrip.com

Someone at the museum was telling me about a wine tasting room just down the road, so I stopped by to check it out. The Northleaf Winery is housed in a mid-1800s building with wine on display clear to the rafters (maybe not clear to the rafters, but the old-wood beams did display some wine). What makes Northleaf unique is that in addition to making some delicious wines, they also produce a line of flavor-infused chocolates that they pair with their wine tastings. I absolutely love the combination of wine and chocolate and cannot believe I have not seen more wineries doing this concept.


While the afternoon was waning, I still had several things on my agenda. I headed back to Janesville and grabbed a quick bite to eat at a local pub called My Apartment, before heading to the Rotary Botanical Gardens for the annual holiday light display. Each year the Rotary Gardens puts on a massive light display. The installation of the exhibit is so large that they start setting up in August. The signature sight is a massive Christmas tree lit up in the middle of a pond. The display has 400,000 lights, a hundred beautifully decorated trees, luminaries lighting pathways and hundreds of dangling icicle lights hung from the tallest trees in the Garden. It is really a wonderful Christmas spectacle, and just one more element in Janesville that further emphasizes the holidays for me.

Christmas Light display in Janesville by MikesRoadTrip.com

My final activity of the evening was just up the street to the Janesville Ice Arena to watch the Janesville Jets play the Minnesota Magicians. I have to admit, I’m not a huge hockey fan, and while I’ve only been to a few professional games, I found this minor league game to be quite exciting. I think the difference is that unless you’re rink side, the action is too far away in those larger arenas. At the Janesville Ice Arena, everyone has a good seat, and if you so choose, you can walk around and stand rink-side next to the glass. It was amazing seeing how fast these guys can skate and how maneuverable they are. After watching this game, I had a whole new appreciation for ice hockey. I found myself glued to the action and nearly missed a unique opportunity.

Janesville Jets photo by MikesRoadTrip.com

The Janesville CVB had arranged for me to ride on the Zamboni during one of the intermissions. I had to use a ladder to climb aboard the massive machine. The passenger seat is positioned backwards while my feet dangled over the edge. Thankfully I was strapped in; otherwise I think I could have easily fallen to the ice as I was taking pictures. I was asking the driver all sorts of questions while watching him move the various levers and maneuver hairpin turns to make another loop. What a fun and unique experience it was! I imagine not many people can say they’ve ridden a Zamboni.

A fair amount of snow had accumulated over twenty-four hours; so on my last day in town I picked up a sled and headed to Palmer Park where I was told had a good hill for sledding. When I entered the park I saw untouched snow everywhere. It was such a beautiful sight as the snow blanketed everything in the park. I soon found the sledding hill and began my assent. Halfway up, I realized I had forgotten my gloves, but my enthusiasm negated the need and I continued walking up the hill. There were only a few people sledding, mostly kids. I asked a small group of boys which was the best line to sled down? They pointed it out and I readied myself. With several swift pushes, I began gaining a lot of speed and veered off course, hitting a bump that sent me flying through the air and into the snow. Now I really needed my gloves! After a quick trip to the car, I headed back up the mountain, to tame the beast. I walked up and sledded down nearly a dozen times before I was just too pooped to do it again.

Winter Road Trip to Janesville WI - Photo by: MikesRoadTrip.com

While my time in Janesville had come to an end, I created many wonderful memories of my experience. To me, that’s what life is all about, the experiences that generate lasting memories. I strive not to live life, but rather to experience it. As a matter of fact, I think if you had to distill life down to a single word, it would be “memories.” And, memories are forged by experiences. In my Road Diary of Janesville, I talked about the amazing coffee and conversation I had with Lucy at Lucy’s Loon Lake. At Mantiques it was the remembrance of my childhood. Then there was the regret for never learning a musical instrument while enviously strumming the strings of a guitar at Voigt’s Music Center. So many experiences in Janesville, and so many wonderful memories that will last a lifetime.

All roads lead to where we go

And where we go is where we’ve been,

So home is just a word we know,

That space in time most apropos

For where we want to be again.

If you’ve ever been to Janesville, or perhaps you live there, please leave a comment and share your experiences and/or favorite aspects. Click here to see more of my photos from Janesville. Click here to read my Road Diary while in Janesville.

A winter road trip to Janesville Wisconsin Pin by MikesRoadTrip.com

Mike Shubic

Mike Shubic is a seasoned road trip travel video blogger, traversing the byways of the world looking for those hidden gems of the road. From unique destinations, unexpected discoveries, creative cuisine, intriguing inns to exciting attractions…the road is his page. The experiences are his ink. And every 300 miles, a new chapter begins. Whether you live vicariously or by example, Mike will do the exploring so you can have an adventure.


  1. Hi Mike! Great read! There was a photo from your post that I would love to make a print of. Do you sell downloads of your photos?

    1. Hi Meghan, thank you so much! I’m working on a way that I can sell my images for this very purpose. Maybe you could check back in a month or so? Thanks again for the kudos. Cheers!

  2. Mike,
    I thoroughly enjoyed reading this. As I lifelong resident of Janesville, it’s so interesting to see it through the eyes of a visitor. Thank you.

  3. I’ve lived in Janesville my entire life. It’s not often that anyone talks about my hometown in such a postive way. Yes when you live somewhere your whole life it tends to just blend together. You managed to capture the beauty of our city in areas that most people wouldn’t look twice at. Thank you for helping me remember why after 31 going on 32 years I still call this place home.

    I hope it’s ok if I share this on my post on my blog.

    1. Hi Kim, thank you so much for the kind words and kudos…much appreciated. Yes, please share on your blog, you can embed the video and link to the original article. Thank you.

  4. I spent my early childhood years in Milton, and both of my parents are buried in the Milton Cemetery, so was interested to see you had visited there. I remember school field trips to the Milton House as a little girl. Still have cousins who live in Janesville. I haven’t been there since 2013 but always like to revisit my old roots when possible.

  5. Loved seeing a visitors version of My Town….lol good job maybe you can come back for so much more in the summertime. Be sure to check out Riverside Park Janesville, Lincoln Tallman Home, World champion Rock Aqua Jay’s, and many more quaint intriguing spots.

  6. Thank you for stopping in Janesville. There are many other historical sights for you to visit and photograph on your next trip here .

  7. Great post! I used to live in Janesville and this made me very nostalgic. Lovely pictures!

  8. Thank you for showing me how wonderful the little town I used to call home truly is!

  9. Mike,
    Loved your fresh look at the city I was born, raised, and lived in my entire 55 yrs. But I hate to tell you Hwy 67 doesn’t come into Janesville. I believe you ended up on Hwys 11 & 14 off of Hwy 67.

    1. Thank you so much Steve. Ugh, really? I got the Highways messed up? The CVB didn’t even catch that. Thank you for bringing it to my attention. 😉 Cheers, Mike

  10. This looks like such a fun winter road trip. My wife and I are definitely putting it on our list of places to go this winter. Thanks for all the info. Oh, and the video was so good!

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