Our Story
Born in a Gas Station Parking Lot
Somewhere between Amarillo and nowhere, we decided that the best travel advice doesn't come from glossy brochures — it comes from people who've actually gotten lost.
160,000+
Miles Driven
48
States Covered
400+
Hidden Gems Found
1
Bad Maps Used
How It Started
Two Squirrels, One Bad Map
It started with a wrong turn on Route 66 in 2019. We were supposed to be in Albuquerque by noon. Instead, we ended up at a diner called 'The Rusty Spoon' in a town with a population of 84, eating the best green chile cheeseburger of our lives and talking to a retired trucker named Earl who'd driven every highway in America twice.
That detour changed everything. We realized the whole travel industry was optimizing for efficiency — fastest route, best hotel points, most Instagram-worthy stops. Nobody was celebrating the wrong turns. So we built Squirrel Jam Travel to do exactly that.
"The best road trips aren't planned. They're survived."
— Earl, retired trucker, The Rusty Spoon Diner
How We Think
Our Travel Philosophy
We believe the journey is the destination — but also that some destinations are genuinely worth the drive.
Embrace the Detour
The best things we've ever found weren't on any map. We build every route with intentional wiggle room for the unexpected.
Eat Where the Locals Eat
If there's a chain restaurant in the parking lot, keep driving. The good stuff is always three blocks off the main road.
Slow Down
America is not a highlight reel. The magic is in the hours between the famous stops — the small towns, the weird museums, the roadside oddities.
Talk to Strangers
Every gas station attendant, diner waitress, and motel owner knows something you don't. Ask them where to go. Listen to the answer.
The Crew
Who's Behind the Wheel
Casey Drummond
Founder & Chief Route Officer
Former cartographer turned road trip obsessive. Has driven Route 66 six times, cried at the Grand Canyon twice, and once spent three days in a town called Truth or Consequences, New Mexico. No regrets.
94,000+
Miles
48
States
Fave
US-50, Nevada
Jordan Reyes
Head of Weird Discoveries
Specializes in roadside attractions, ghost towns, and diners that look like they haven't changed since 1962. Maintains a personal database of 400+ off-map stops. Drives a 1987 pickup truck named Gerald.
67,000+
Miles
42
States
Fave
Beartooth Highway, Montana
Why Us
What Makes Squirrel Jam Different
We've Actually Driven It
Every route we recommend has been driven by us, personally, in a real car, with real snacks and real arguments about which podcast to play.
No Sponsored Content
We don't take money from hotels, attractions, or diners to recommend them. If we say it's worth stopping, it's because we stopped and it was worth it.
We Celebrate the Weird
The world's largest ball of twine is a legitimate destination. We will defend this position until we die.
Ready to Get Lost?
Tell us where you want to go — or better yet, tell us you have no idea — and we'll build you a route worth remembering.