How to Plan a Road Trip With Friends
9 months ago
A drivetrain malfunction has our convoy stopped on the side of H-58, a winding dirt road in Michigan’s Upper Peninsula. Not knowing the first thing about automobiles, I kick rocks while the professionals and well-practiced amateurs poke and pry beneath the hood. Unscheduled intermission aside, we’re grateful for the break, a chance to stretch legs and catch up with our fellow travelers. It’s a Friday afternoon in October and we are 400 miles into the Mille Mitten, a three-day, three-night, thousand mile road rally around the Great Lakes State.
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Mille (pronounced mee-lay) was born in 2012, when two friends, Matt and Megan, decided to squeeze the most out of a quick weekend visit by taking a last-minute road trip throughout Michigan. After meeting up with Ben Bator (full disclosure: my brother! My just-mentioned friends!), they stopped for the night at Matt’s family cabin. Recounting their favorite sights over a wine-soaked dinner, Ben butted in with a selfish, albeit great idea–if a Michigan native like Megan hadn’t seen much of what makes the area so beautiful, what about everyone else? Why not do a similar trip but invite a group of 20 friends, spanning born-and-bred New Yorkers, heartland homebodies, and coastal California purists, to come on the road trip of a lifetime?
Drunk on dreams of showing off the state’s grandeur (and also drunk on wine), Ben and Matt decided to go for it. The route was mapped, dates were set, and friends were invited. In homage to Italy’s famed open-road endurance race, the Mille Miglia, they decided to name the trip Mille Mitten–a thousand-mile grand tour of the place that raised us.
Over the course of six years, Mille has hosted 80 individuals from around the country, managing to pack in boat rides on Lake Superior to see the Pictured Rocks, secret beach picnics, Travis Scott-soundtracked backroads, 10-car convoys through the densely-forested Tunnel of Trees, and chasing sunsets all over the state in the course of a single weekend each year. Out-of-towners and locals alike leave the convoy with a new appreciation for our state’s beauty–sometimes breathtaking, sometimes quiet, always worth seeing for yourself.
Excuses to avoid this kind of travel run long in 2017. Is it really worth it to spend that much time in the car? Shouldn’t these quick-jump vacations be left to the SkyMile high rollers? What about catching up on the Netflix queue? Answers, in short: yes, no, hell no. A road trip is freedom from anyone’s schedule but your own. In 20 years, your kids won’t be begging to hear about the time you binged Stranger Things in one weekend. Head out to actually see and experience what’s beyond the apartment walls. And take pictures, the kids might want some proof.
As I type this, an old roommate treks his way east from California, taking in the redwoods of Big Sur, winding his way through the Sierra Nevada, and camping out underneath the stars. After spending years at a windowless desk job buried in paperwork, he decided to quit the gig and hit the road with a mission to see the country. Judging by his Instagram feed, the last month has been one huge X through anyone’s bucket list. Massive hikes, moonlit roads, and empty parks abound. And aside from run-ins with laundromat employees and the occasional brown bear, he’s traveling solo. Next week, he’ll meet me in Austin for a few days off from driving before the final push back to his starting point in Michigan.
Wow, sounds awesome, you’re thinking, but there’s no way I can quit my job (fair!) or organize a 20-person convoy (a little excessive!) just to get out of town for a bit. But here’s the good news–taking a great road trip is easy and you can do it too. Here’s how.
You don’t need grand plans, you just need plans.
Pick something within 350 miles of your front door. It could be anything. A state park you’ve seen only on Instagram? Go for it. Some restaurant a friend once went to? Make a reservation and hit the road. A too-cool-to-be-true Airbnb cabin in the woods? Yup. Though every good trip is about the journey, you still want to aim for a destination.
Off-season has its benefits.
Who wants to burn all that daylight stuck in traffic? Off-season is the way to go. You’re bound to encounter much quieter roads, you can actually see the sights of nature instead of selfie stick-wielding tourists, and you’ll save a few bucks on hotel fees.
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Google Maps and Waze are your best friends.
To cherry pick back roads and find alternate options, get familiar with your surroundings before heading out. Plug in your starting and endpoints on Google Maps, then do some scrolling to discover routes more interesting than the main highways. Pro tip: Street View is a necessary planning tool, especially helpful in dirt road discovery or avoidance. Waze is great for on-road navigation and crowdsourced cop awareness (not that you’d speed anywhere).
Pick your co-pilot(s) wisely.
If you can’t spend a few hours together without frantically searching for an opportunity to bail, then it’s a good idea to leave that person at home. The ideal co-pilot is a jack-of-all-trades, able to navigate the turns, keep a conversation going, quickly spot a potential snack stop, and handy with the playlist. If nobody fits the bill, going it alone is still more satisfying than sitting on the couch.
No car, no excuses.
And always pack a bathing suit.
Even in the dead of winter, you never know.