Alaska Bound! Rest Area, Funeral Home and a State Park
Three. Two. One. Ignition – Lift Off! The Kentucky Bluegrass was quickly in the rear view mirror as our road trip to Alaska took off. The flat landscape of Indiana and Illinois quickly passed as we were determined to get this epic adventure officially started.
As we rolled into Wisconsin, hills and valleys gradually emerged as if to foreshadow the magnificent Canadian Rockies and beyond that are in our sights.
Our departure day on Friday, May 8, 2025 was hectic at best. The van was in the Sprinter shop getting new side view mirrors, and we were out of there by noon. Back to our friends at Sugar Hill Farm in Kentucky to finish loading the van, stocking the fridge and finalizing a few adjustments from our shake-down trip the previous week.
The fifth wheel RV needed to be cleaned and prepped for storage. By early evening we were headed an hour away to park the RV and truck for the next five months. We still needed to do laundry so everything was left clean in the RV for our return.
By ten o’clock in the evening we were finally headed north for five months in the Pleasure Way camper van. We were definitely excited as this journey to Alaska was becoming a reality. We drove 100 miles north before we pulled into the Taylorsville Rest Area on I-65 between Louisville and Indianapolis.
First night was quiet and comfortable at the rest area, and everything was off to a great start.
Day 2 (May 9th) was surreal, cruising north through Indiana and crossing over into Illinois, realizing we were literally starting a bucket list journey and the excitement was palpable. Still a little anxious to push onward and get out of familiar territory, we rolled on 350 miles.
Practical stops were on tap for this day. Lunch at a rest area on Interstate 39, a stop at Love’s truck stop to fill our propane and top off our water, and a few groceries at Schnucks each took some coordinating, but we maneuvered through these new aspects of van life.
As a preface to our second night, there’s a program called Harvest Hosts, where places like wineries, breweries, museums and many others allow RVers to park free for the night. Although it varies by location, typically its just boondocking in the parking lot, and in exchange there’s typically an expectation to take a tour or buy a bottle of wine in exchange for the free night.
All of that said to explain our second night was at a funeral home. Yes, a funeral home. Out in the parking lot, of course! I have absolutely no idea why they signed up to allow RVers to stay, but it was a huge parking lot with large grass fields and actually a pleasant environment. We simply parked in the back corner and stayed the night in our self-contained camper van.
A little strange, especially with the full moon illuminating both the night sky and our imaginations, but we feel very fortunate that the owners of this funeral home voluntarily provide a free place for RVers to stop briefly overnight with nothing expected in return. If anyone ever needs a place to boondock, Grace Funeral Home in Rockford, Illinois is quiet, spacious and free and available through the Harvest Host program.
Day 3 (May 11th) we convinced ourselves this trip was in fact a reality and it was time to slow down and embrace van life. It’s a delicate balance between making gains on the 4,000 miles we have just to arrive at the Alaska border versus relaxing, smelling the spring flowers, appreciating the scenery, exploring the micro-cultures along the way and just enjoying the journey at a reasonable pace.
Out of the funeral home parking lot in the morning and on to the Milton House in Milton, Wisconsin – a stop on the Underground Railroad with an underground tunnel from the formal Stagecoach Inn that pops up discreetly in a nearby log cabin. Unfortunately it was not open for tours, but still an impressive feat of people helping people under adverse conditions.
Heading out of Milton we saw The Meat Market and stopped for some fresh hamburger, sausage and smoked beef meat sticks. All to complement the Wisconsin staple – cheese curds that we had just picked up.
Next was a tour of the Taliesin House in Spring Green, Wisconsin, designed by and the home of, noted architect Frank Lloyd Wright for nearly five decades. He treated his home as a laboratory of sorts, continually experimenting with new materials and testing new ideas. Although Wright was obviously a prominent architect, it was somewhat disappointing to learn his personal life was unsavory at best. A great two-hour tour through his eccentric home including living quarters, working areas, and agricultural areas that once spanned 2,700 acres.
Following the initial push of 600 miles in the first couple days, we settled in at Devil’s Lake State Park in Wisconsin for two nights.
Stay tuned for more vanlife roadtrip to Alaska updates! Thanks for coming along on the journey.