How to Plan a Cross-Country Road Trip + 4 Routes You Have to See for Yourself

When it comes to summer vacations, planes and trains will get you far—but there’s nothing quite like a road trip.Windows rolled down, the perfect favorite playlist turned up, and nothing but open road for miles ahead: this is the kind of journey where getting there really is half the fun. And with nearly 312 million square miles of  geographically varied terrain spread across the 48 contiguous United States, it’s no wonder they call it a Great American Road Trip. Simply put, there may not be a more quintessentially American way to travel.

Earlier this year, we shared some of our favorite road trip routes along the West Coast, as well as our can’t-miss routes along the East Coast. Each list reveals a few of the spectacular slices of life you’ll find when driving through the Pacific- or Atlantic-facing states. But for those with a little more vacation time to spare, and who wish to see and appreciate the true diversity of the USA up close? Only a cross-country road trip will do—and summer is just the right time to do it. Here, we’re sharing a few of our favorite tips to get you ready for that next cross-country expedition, along with four of our favorite long-distance routes to add to your list.

Road Trip 101

Nail Down Your Philosophy

Your trip timing may be at the mercy of work and school vacation schedules, but there are still a few key questions to answer. For example, how long can you be away, and how far do you want to go? Do you have time to drive both ways, or would you rather spend the whole vacation driving one direction, then hopping a quick flight or train back home when it’s all said and done?

This is also a good time to ask yourself what kind of road tripper you really are. To some, the trip is about reaching a far-flung destination with a few pre-determined stops each day—things like veering off for lunch at a famous diner, or checking out a quirky roadside attraction along the way. To others, the journey is all about the surprises each new day will bring, in which case you may prefer to keep the itinerary a bit more flexible. 

One solid way to plan your trip is to decide upfront how long you want to spend in the car each day. For example, driving from New York City to Chicago (about 790 miles) would take around 13 hours if you were to drive straight through. Technically possible, but where’s the fun in that? If you know you’ll want to stop several times along the way, consider spending 6 or 7 hours per day on the road and giving yourself two full days to get there—or even longer, if you have many stops in mind.

Decide What to Drive

Now that you have your dates set, first thing’s first: a road trip of any length and duration means you’ll need a car. If you’re planning to use your own, be sure it’s gassed up and has had a recent oil change or service. The last thing you’ll want on your big road trip is a major mechanical issue or blown tire along the way, so check your  tire pressure and tread (including the spare) before heading out, as well. 

If you’ll be renting a vehicle, it takes some of the guesswork out of the maintenance parts of the equation. Choose a comfortably sized option with enough room to keep you and your passengers cozy and cool, but ideally something with reasonable fuel economy, such as a midsize sedan or small SUV. Just be sure to rent from a reputable rental car company, and have a  roadside assistance number somewhere handy. Odds are, you won’t need it—but better safe than sorry.

Pack Like a Pro

When it comes to packing for a car (much like the rule of thumb for carry-on bags), remember: less is definitely more. Keep it light and pack layers to maximize your cargo space while keeping prepared for every kind of weather. Beyond that, here are a few of our other favorite road trip-specific packing tips:

• Pack into small backpacks or duffels for various purposes, such as a bag for your outer layers, and another bag for snacks. Using small, soft-side cases makes it easy to stuff them in small spaces like backseat floorboards, while keeping what’s inside within easy reach during your drive. Plus, a well-packed backpack makes an easy grab-and-go bag for quick overnights in a hotel without the need to unpack the whole trunk each time.
• Store a mini road trip kit in each car door, containing all the necessities you and your passengers might need along the way: a small packet of tissues, hand sanitizer, a bottle of water, and a travel size sunscreen to keep everyone protected from the sun’s rays throughout the drive.
• Bring along a road atlas or print out and tuck away hard copies of a map showing your route with a few of your planned stops along the way. Whether you rely on your favorite Maps app or the GPS within your car, it’s always a good idea to have a backup for any areas where service may be spotty. 
• Don’t forget the snacks! Pack plenty of healthy options for food as well as hydration—even just sitting still in a warm car, you can become dehydrated without realizing it. (Pro tip: Consider bringing a small cooler so you’ll always have ice-cold beverages on deck, even in the hottest months of the year.)
• While having the ability to access proper roadside assistance is a must, pack your own kit for mini roadside emergencies. This should include a flashlight or small camping-style headlamp along with spare batteries, a tire pressure gauge, jumper cables, a small first aid kit, extra snacks, water and a few lightweight but warm blankets.

4 Incredible Cross-Country Road Trips

You’re packed and ready—now, where to go? These four cross-country road trip routes are some of the best places to start. 

Route 66: The Mother Road

Easily one of the most notable and iconic highways in the world, Historic Route 66 is a classic cross-country route and a great place to start. First paved back in 1926, and winding through dozens of small towns throughout the country, it has been dubbed “the Main Street of America.” It connects downtown Chicago to Santa Monica Pier in Los Angeles, crossing eight states and three time zones, with charming and quirky stops around every turn. It spans around 2,400, but most experts agree you’ll want a full three weeks to tackle this monster route. That amount of time will help you maximize the many worthy stops, and it takes into account the fact that old Route 66 is technically “decommissioned” today. You can still drive on about 80% of the old route, and it’s safe—but expect a few bumps and detours throughout your journey. 

US-50: The Loneliest Road

We’ve all heard the song America the Beautiful, but this route gives new meaning to the expression “from sea to shining sea.” Spanning over 3,000 miles and touching parts of 12 states and the nation’s capital in Washington D.C., it’s been dubbed “the Loneliest Road” because there are so many stretches of serene solitude on its path. (In particular, it gets its nickname from particularly isolated parts of highway in Nevada.) You’ll need about two weeks to do it right, but this cross-country route packs a punch: you’ll see both coasts along with the Great Plains, both the Appalachian and Rocky Mountains, the Sierra Nevada, and even portions of the old Pony Express National Historic Trail. With so many of the country’s geographical monuments and a piece of our own postal history, it’s no wonder Time magazine once called this scenic route The Backbone of America. 

US-20: The Oregon Trail

This route is true to its name, tracing much of the original Oregon National Historic Trail in parallel, and making it ideal for history buffs. The preferred route is to head from east to west, since it allows you to drive into the setting sun and enjoy longer days. But west to east offers better views of the Oregon Trail itself. Either way, you’ll head from Massachusetts to Oregon (or vice versa) for over 3,300 miles—a journey of at least two weeks through various climates, so pack accordingly. Along the way, you can stop in such varied locations as Cape Cod, Niagara Falls, Chicago, Mount Rushmore, Yellowstone National Park (depending on its reopening schedule), the Badlands, Custer State Park, and even the Columbia Gorge. There are also favorite stops like the Rock and Roll Hall of Fame, Cedar Point amusement park, and even the original Field of Dreams in Iowa. 

US-80: The Southern Pacific

With so many stops throughout the tasty American south, you’ll want to bring your appetite for this one. Also known as the Old Southern Route, this path follows old US-80 (and a few of its newer replacement roads and detours in some parts) for around 3,000 miles, give or take where you hop on and off. For that reason, note that the road will change names a number of times along the way. Starting in sunny San Diego, you’ll head east for a few weeks at your own pace, passing through New Mexico and West Texas before entering the bayou. From the Mississippi Delta to the Appalachians and on to the east coast, this route is a stunner with frequent topographical and cultural changes as you go. One thing’s for sure: you won’t go hungry. Load up on tacos and southwestern fare while you’re in the west, then dine on fresh catfish, Creole cuisine and barbecue as you make your way through Louisiana, Mississippi and Alabama. Once in Georgia, stop for fresh Atlantic seafood before you start planning your foodie tour back west.