3 Generation Motorcycle Road Trip

Tommy on the Tail of the Dragon - 16 years old from Washington!

The adventure was supposed to be a “state-collection” road trip. My mom has this habit of collecting things—continents (yes, even Antarctica), oceans, and lately, motorcycle miles. By 2021 she had already ridden in all 50 states and set her sights on knocking out all 13 Canadian provinces. She also wants to visit every country on Earth… some of which she may or may not have entered through the usual front door. My mom is one of the most adventurous people I know, so when she asked me to join her on this mission, I felt honored. What made the trip even better was that my 16-year-old son would be riding with us on his own bike.

This wasn’t going to be a sightseeing tour—this was a mileage mission. A “collect them all” type of ride. We planned in a week of downtime, but the route itself was built for efficiency. Originally, we set out to ride 46 of the lower 48 states, skipping California and North Dakota because Mom already had them under her belt. Let’s just say that plans change.

We woke up on August 1st, 2015, at 4 a.m., and by 5 we were rolling out the door. Our bikes were packed from the night before. My son and I hopped on the scoots, and my wife and daughter followed in the car for the first day. We rode out of Shelton, Washington in the dark, heading to Olympia to meet up with my mom.

Washington → Idaho → Montana

The ride across eastern Washington was uneventful except for the wildfire smoke and ash raining down in Moses Lake. Idaho and Montana were full of the usual I-90 construction. Honestly, I’ve been riding that road since 1987 and I don’t think I’ve ever seen it construction-free.

I’m not much of a freeway flyer—I prefer quiet two-lanes—but when you’re trying to cover states fast, high-speed interstates are your friend. Idaho was posted at 75 mph, Montana at 80, so we made good time.

My son’s little Yamaha Bolt only carried about three gallons of fuel, so we were stopping every 120 miles or so. Honestly, I didn’t mind. I was riding my dad’s borrowed 2011 Harley Ultra Classic because my Dyna started acting funny two days before we left. I removed the trunk and swapped the windshield, but even stripped down, the cramped riding position had me begging for breaks. That little 3-gallon tank of my son’s became a blessing.

Tommy’s Bolt was set up minimalist—spring solo seat, no saddlebags, no windshield, just a tank bag and the open road. People say riding cross-country without bags or a windshield isn’t smart. Maybe it isn’t. But I’ve done it, he’s done it, and we’ll both do it again.

Mom rode her beloved 2012 Heritage Classic—bone stock—and she wouldn’t change a thing.

We crossed into Idaho, climbed over the Continental Divide, and rolled through some surprisingly fun interstate curves. We made it to St. Regis, Montana, and grabbed a room at the Super 8.

Montana Sunrise → Sturgis

We left at dawn the next morning after saying emotional goodbyes to my wife and daughter—four weeks apart was going to be rough. My wife is my best friend and we rarely spend more than a day or two apart. But the mission was calling.

The fire-orange sunrise was gorgeous as we crossed Montana, Wyoming, and into South Dakota. At Spearfish we jumped off the freeway and rode Spearfish Canyon—slow because of rally traffic, but absolutely worth it.

Sturgis was… Sturgis. The 75th Anniversary Rally, or as I call it, “Trailer Week,” brought roughly 700,000 of our closest friends. We stayed in Whitewood at the Iron Horse Inn, which was perfect. Bikes right outside the doors, mostly under cover, and a shuttle into town.

We walked Main Street, checked vendors, ate too much food, and soaked in the atmosphere. Sturgis is something every rider should experience once. For some people, once is plenty.

Storms, Luck, and the Rolling Plains

South Dakota’s weather was wild that year, but somehow we dodged every storm. Mom watched the Weather Channel religiously every night, and honestly, I think that saved us more than once.

At Wall, SD, we planned to eat breakfast and wander around, but one look at the black sky and we bailed. Breakfast could wait. Badlands could wait too. Staying dry beat everything.

Just before Minnesota, another rider told us he left Wall 15 minutes after we did—and rode through heavy rain for hours. We escaped by dumb luck.

We pushed farther than planned that night to stay ahead of the storm.

Midwest Homecoming

We crossed Minnesota farm country, into Iowa, then Wisconsin. By staying off the interstate we pushed my son’s tank to the limit—160 miles—but he managed 70 mpg on the backroads.

We stopped in Monroe, Wisconsin at Baumgartner’s Cheese Store and Tavern—an old family favorite. They warm Mrs. Mikes potato chips in the microwave, which sounds odd, but trust me… they’re amazing. Greasy, salty, warm perfection.

After Monroe, we rolled into Freeport, Illinois for a small family reunion, a tour of our old town, and root beer coolers in Lena.

Milwaukee → Michigan Ferry

The next day we visited House of Harley in Milwaukee—a historic, friendly shop I instantly fell in love with. Then we boarded the high-speed ferry to Muskegon, Michigan. Compared to Washington’s ferries, this thing was luxury. Smooth, quiet, fast.

All motorcycles had to be tied down. Tommy secured his bike, I strapped down mine and Mom’s.

We met a French couple traveling the Great Lakes for a month. Tommy learned the hard way that there’s a Sturgis in Michigan after proudly pointing to his “Sturgis” shirt. Geography lesson delivered.

New England and the Storm

Michigan gave way to Indiana and Ohio, and that’s where drivers started getting crazy. Then the weather caught up.

We skipped Niagara Falls because the storm would’ve swallowed us. Instead we cut through New York, New Hampshire, Vermont, and into Maine—where Mom touched the Atlantic with her bike for the first time. My son thought it was hilarious that he reached the Atlantic by motorcycle before ever riding to the Pacific, despite living an hour from it.

We rode south into Massachusetts and finally got caught by the storm, so we waited it out a day.

I didn’t care for the Northeast—too busy, too frantic, too aggressive. All I wanted was to get back to friendly roads and friendly people.

Pennsylvania → D.C.

Pennsylvania’s Amish country surprised me—tractors, power lines, credit card machines… not quite what I expected. The scenery was gorgeous, but the locals weren’t thrilled with us.

We watched a hot air balloon inflate and launch behind the hotel, unexpectedly calming after stressful riding.

Washington D.C. the next day went surprisingly smoothly. We hit the Marine Corps Memorial, the Vietnam Wall, the Korean War Memorial, and Arlington. A disrespectful tourist got chewed out by the Sergeant during the Changing of the Guard—rightly so.

Skyline Drive → Blue Ridge → The Bear

Finally, we reached Skyline Drive. This was the kind of riding I’d been craving: miles of curves, wildlife everywhere, and peace.

Then came the bear.

A huge one stood ten feet off the road. I knew I could outrun it, Tommy probably could, but Mom? She’d stop and try to pet the damn thing. We kept our distance until it wandered off and continued on.

Virginia → West Virginia → Real America

In West Virginia we hit a gas station with busted pumps. Two locals—classic good-ol-boys—helped us out. One saw our Washington plates and hollered, “Dang gum, you’s far from home!” But honestly, I felt at home there. They were kind, humble, no rush, no attitude. I missed that.

We rode the road they warned us not to take—steep, twisty, cliff-hugging—and it was one of the best stretches of the trip.

Carolinas → Georgia → Tail of the Dragon

We soaked up Virginia, dipped into North Carolina, and crossed into Georgia for the night. The next morning we hit Moonshiner 28, then Deals Gap.

That’s where the bees attacked me. Full-face helmet, visor cracked for airflow—big mistake. I got stung repeatedly, including right under the eye. I bought a beanie helmet the instant we found one. I would’ve paid triple.

Then we rode the Tail of the Dragon: 318 curves in 11 miles. Overhyped? Yeah. Worth it? Absolutely. Riding it again? Definitely.

Tennessee → Midwest → Home Stretch

Tennessee was lush and beautiful. Nashville was pleasant. Kentucky was quick. As we neared Illinois—the land of no helmet laws—I ditched my lid on the bridge and my son flipped me off from inside his full-face. Fair play.

Southern Illinois tried to drown us with rain, but once again, we dodged it by minutes.

Missouri, Kansas, Nebraska—tornado warnings everywhere—but thankfully no direct hits. The haze from the West Coast wildfires followed us from Nebraska to Colorado to Wyoming.

At Bonneville Salt Flats we couldn’t resist running the bikes on the salt. I’m still finding salt in the Ultra years later. Worth it.

We spent the final nights in Idaho, Oregon, and Washington. The smoke was thick enough to change the color of the sky. My wife met us in Tri-Cities, and we treated ourselves to one last night in a hotel together.

Crossing White Pass into Olympia and finally back to Shelton felt incredible. I swapped back onto my Dyna—my real bike—and my son and I finished the trip riding side-by-side.

Final Thoughts

It was an unforgettable trip: no breakdowns, no wrecks, barely any rain, and endless stories. My son rode like a champ, Mom knocked out a ton of new states, and I got to share a once-in-a-lifetime adventure with two generations of family.

And I can’t wait to do it again—next time with my wife along for the ride.