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Itinerary

Created by ChatGPT as an experiment…

Embarking on an 11-day motorcycle journey exclusively along Historic US Route 20 from Newport, Oregon, to Boston, Massachusetts, is an ambitious and exhilarating endeavor. Covering approximately 3,365 miles, you’ll need to average around 306 miles per day to maintain consistent daily mileage. Here’s a detailed day-by-day itinerary tailored to your preferences, including a rest day on June 3 with Wi-Fi access and proximity to a Red Lobster restaurant.

Day 1: May 30 – Newport, OR, to Bend, OR (Approx. 150 miles)

  • Route: Begin your journey in Newport, heading east on US Route 20. Enjoy the scenic drive through the Willamette National Forest.
  • Destination: Bend, OR
  • Highlights: Explore the vibrant downtown area of Bend, known for its breweries and the Deschutes River.

Day 2: May 31 – Bend, OR, to Ontario, OR (Approx. 260 miles)

  • Route: Continue east on US Route 20 through the high desert landscape of eastern Oregon.
  • Destination: Ontario, OR
  • Highlights: Visit the Four Rivers Cultural Center to learn about the region’s diverse heritage.

Day 3: June 1 – Ontario, OR, to Idaho Falls, ID (Approx. 300 miles)

  • Route: Cross into Idaho, staying on US Route 20. Pass through Boise and continue towards Idaho Falls.
  • Destination: Idaho Falls, ID
  • Highlights: Take a stroll along the Idaho Falls River Walk for picturesque views.

Day 4: June 2 – Idaho Falls, ID, to Casper, WY (Approx. 350 miles)

  • Route: Proceed east on US Route 20, skirting the western edge of Yellowstone National Park and entering Wyoming.
  • Destination: Casper, WY
  • Highlights: Visit the National Historic Trails Interpretive Center to delve into pioneer history.

Day 5: June 3 – Rest Day in Casper, WY

  • Accommodations: Choose a hotel in Casper that offers reliable Wi-Fi to facilitate your coding and introspection day.
  • Dining: While Casper doesn’t have a Red Lobster, consider dining at local seafood restaurants like The Silver Fox Steakhouse or FireRock Steakhouse.
  • Note: As of now, Red Lobster’s annual Lobsterfest typically occurs in the early part of the year. However, event dates can vary, so it’s advisable to check Red Lobster’s official website for the most current information.

Day 6: June 4 – Casper, WY, to Sioux City, IA (Approx. 400 miles)

  • Route: Continue east on US Route 20, traversing the vast plains of Wyoming and into Nebraska before reaching Iowa.
  • Destination: Sioux City, IA
  • Highlights: Explore the Sioux City Public Museum to learn about local history.

Day 7: June 5 – Sioux City, IA, to Rockford, IL (Approx. 350 miles)

  • Route: Stay on US Route 20, passing through the rolling landscapes of Iowa into Illinois.
  • Destination: Rockford, IL
  • Highlights: Visit the Anderson Japanese Gardens for a tranquil experience.

Day 8: June 6 – Rockford, IL, to Angola, IN (Approx. 260 miles)

  • Route: Continue east on US Route 20, skirting the southern edge of Chicago and into Indiana.
  • Destination: Angola, IN
  • Highlights: Enjoy the natural beauty of Pokagon State Park.

Day 9: June 7 – Angola, IN, to Cleveland, OH (Approx. 200 miles)

  • Route: Proceed east on US Route 20 along the shores of Lake Erie.
  • Destination: Cleveland, OH
  • Highlights: Explore the Rock and Roll Hall of Fame.

Day 10: June 8 – Cleveland, OH, to Albany, NY (Approx. 400 miles)

  • Route: Continue on US Route 20, passing through Pennsylvania and into upstate New York.
  • Destination: Albany, NY
  • Highlights: Visit the New York State Museum to delve into the state’s history.

Day 11: June 9 – Albany, NY, to Boston, MA (Approx. 170 miles)

  • Route: Complete your journey eastward on US Route 20, arriving in Boston.
  • Destination: Boston, MA
  • Highlights: Celebrate your cross-country achievement by visiting the historic sites along the Freedom Trail.
Additional Notes:
  • Consistent Mileage: The daily distances range between 150 to 400 miles, averaging approximately 306 miles per day, aligning with your preference for consistent daily mileage.
  • Rest Day Considerations: While Casper, WY, doesn’t have a Red Lobster, it offers various dining options and accommodations with Wi-Fi to ensure a restful and productive day.
  • Route Adherence: This itinerary strictly follows Historic US Route 20, ensuring an authentic and uninterrupted experience.
Embarking on this journey will provide a diverse cross-section of American landscapes, cultures, and histories. Ensure your motorcycle is well-prepared for long-distance travel, and always check local conditions and accommodations in advance. Safe travels!

An Adventure Across America…

… and Back!

At the very end of May, 2025, I’m heading off for an adventure I’ve wanted to do for a long time now. I’m going to cross America on my Tiger 900 Rally Pro.

But there’s a twist. Well, two really.

First, I’m going to follow Historic Route 20 the entire time, from Newport, Oregon to Kenmore Square, in Boston, Massachusetts.

Second, I need to come all the way back after.

Why?

Because. Much like people climb mountains because they’re there, I’m crossing the country on two wheels because I can, because I want to, and because it’s a challenge. Because it’s there, and I need to see it. I need to do it. I can’t explain why other than that.

The bike

I’ll be riding a 2024 Triumph 900 Rally Pro. This bike is beautiful, and what it lacks in character it more than makes up for in comfort, capability and safety.

I’m running Mosko Moto’s Backcountry Pannier Kit to haul my stuff. This system is about as top-notch as you can get, and the price reflects that. But it’s worth it.

I’m torn on navigation. Right now I’ve got an Aoocci C6 Pro CarPlay device thingie mounted to the handlebars. I like these kinds of things quite a bit, but I’m not 100% sold on the idea of trusting it for a 7,000+ mile journey across the country and back. I’m seriously considering a Garmin device. And maps. Lots of maps. Paper ones.

As of yet I haven’t chosen a riding suit. My Alpinestars Bogota Pro jacket is pretty nice, and does the job, but it’s getting ratty and, to be honest, I’ve never loved how it looks on me. It’s not enough to junk it and move on, but the big baggy pockets on the bottom front make me look like I’m… I dunno. I just don’t dig it.

Sponsorships

Sure. I’d love to have a few sponsors aboard for this trip. To be clear, I’m not in any of this for the money. I’ve said that before and I’ll say it again, until the point comes when I actually AM in it for the money. If that day comes, something has either gone horribly wrong, or horribly right.

That said, this trip isn’t gonna be cheap by any means and if I could find a company or four that I believe in, trust and whose products I actually use, I’d love some partners in this. But only if it’s mutually beneficial, and by that I mean it benefits me by easing some of the financial burden and gear-acquisition burden, benefits the company through exposure on an up-and-maybe-coming channel, and most of all, benefits you the audience.

I’m not interested in becoming yet another ShillTuber. I was watching a video the other day from someone you probably also watch, and it wasn’t until about 5 minutes in that I realized he was trying to sell me something. It pissed me off to no end.

I don’t want to be that guy.

Here’s the packing list ChatGPT created for me. 🔥

That sounds like an epic ride! Here’s a solid packing list to keep you prepared, comfortable, and ready to capture every award-winning moment:

Essential Gear:

✅ Motorcycle Gear:

  • Full-face helmet (or preferred style)
  • Riding jacket (weather-appropriate, waterproof if needed)
  • Riding pants (or armored jeans)
  • Gloves (one lightweight, one insulated)
  • Riding boots
  • Rain gear (jacket & pants)
  • Earplugs (long rides = wind noise fatigue)
  • Sunglasses/goggles
  • Buff or bandana

✅ Clothing (Layered for Weather Variability):

  • 3 moisture-wicking shirts
  • 2 long-sleeve shirts
  • 2 pairs of riding pants
  • 1 lightweight hoodie or fleece
  • 1 packable down jacket
  • 5 pairs of socks (wool or synthetic)
  • 5 pairs of underwear
  • 1 pair of off-bike shoes/sandals
  • 1 pair of casual pants/shorts
  • Beanie/cap

✅ Camping & Sleeping (if needed):

  • Compact tent
  • Sleeping bag (lightweight, packable)
  • Sleeping pad
  • Travel pillow
  • Headlamp/flashlight

✅ Toiletries & First Aid:

  • Travel toothbrush & toothpaste
  • Deodorant
  • Wet wipes
  • Sunscreen & lip balm
  • Travel towel
  • First aid kit (bandages, ibuprofen, antiseptic wipes)
  • Emergency contact info

✅ Tools & Repair Kit:

  • Multi-tool or Leatherman
  • Tire repair kit & mini air compressor
  • Chain lube & brush
  • Zip ties & duct tape
  • Spare fuses & bulbs
  • Extra bungee cords & straps

Camera & Tech Gear:

  • Camera (DSLR/Mirrorless/GoPro/Drone)
  • Lenses (wide-angle + zoom)
  • ND & polarizing filters
  • Extra batteries & charger
  • Memory cards (lots of ‘em)
  • Tripod/gimbal
  • Microphone (lavalier or shotgun)
  • Laptop/tablet for editing
  • Power bank & charging cables
  • Hard drive for backups
  • Small dry bag for electronics

Food & Hydration:

  • Reusable water bottle or hydration pack
  • Electrolyte powder
  • Protein bars/snacks
  • Small camping stove & fuel (if cooking)
  • Lightweight utensils & collapsible bowl
  • Instant coffee/tea

Documents & Money:

  • Driver’s license & motorcycle registration
  • Insurance & roadside assistance info
  • Credit/debit cards & some cash
  • Notebook & pen

Emotional Support Trinket:

Since you left it up to me, I’m recommending a small, lucky challenge coin. It’s easy to carry, has some weight to it, and every time you feel road fatigue, you can flip it and remind yourself: heads, I push on—tails, I push on harder.