Labor Day is right around the corner, the quintessential long weekend for road trips. The perfect last hurrah of summer in which to toss your dog in the car and hit the road and take a little road trip. It’s woven into the fabric of the American Dream, our god given right to hop in the car, fill up the tank and take off on an epic road trip of days, weeks, or even months, cruising the backroads and highways of America. Finding inspiration in small towns, endless vistas, and the joy of the open road.

But a trip like that takes time, time that many of us simply don’t have. Those of us who can’t get away to drive the length of the US always feel a twinge of jealousy and longing to feel that freedom. With a slight adjustment of your mindset, you can enjoy the endless possibilities of a traditional road trip in just a few days. Whether you live close by or will be flying to and from your starting and ending points, here are some ideas to get you started planning your own great American road trip that can be done in three to five days.

With its small size, you can cover a lot of states in New England in a short amount of time. If you drove without stopping New York City to Portland, Maine, you’d be looking at 7 hours in the car and you’d pass through, Connecticut, Massachusetts, Rhode Island, and New Hampshire. But you’d also miss out on a lot of small towns, winding country roads, idyllic farmland scenes, and New England charm. Instead, give yourself 3-4 days to see a bit more of this region. Make the trip in autumn and your visit will coincide with the arrival of some of the most stunning fall foliage you’ve ever seen.

Flying into New York may be the cheapest option, but you could also arrive at Newark or Philadelphia to make this journey. Start by driving from New York City to Mystic, Connecticut along the coast, which will take about 3 hours in light traffic. Visit the Denison Pequotsepos Nature Center, sip and swirl at several nearby wineries, dine at the legendary Mystic Pizza, stroll along the seaport, or drive a few miles north to one of Rhode Island’s beaches. It’s also less than an hour’s drive to Providence or Newport, Rhode Island where you can explore a historic city or marvel at magnificent houses and scenery as you amble along the Newport Cliff Walk.

From Mystic, drive just over 2 hours to Salem, Massachusetts. Wander Pickering Wharf and the Salem waterfront and downtown, and explore the sordid history of the Salem Witch Trials at the Salem Witch Museum. Visit Nathanial Hawthorne’s birthplace at the House on Seven Gables, go whale watching off the coast, take a ferry to Boston, or spend a day on Cape Cod. It’s another 2 hours of driving along the coast from Salem to reach Portland, Maine. Explore the working waterfront of the Old Port, or browse the many galleries of the Arts District downtown. For a look at some of the area’s varied animal life, head to the Maine Wildlife Park, where you can spot animals like bobcats, gray wolves and moose. Check out lighthouses, or go deep-sea fishing and whale watching.

• Best time to make the trip: Spring and Autumn
• Minimum days needed: 3

>> Find flights to New York, look for hotels in Philadelphia or find things to do in Portland, Maine

The “Rust Belt”, those Midwest cities that, up until the last few decades anyways, were founded on manufacturing, aren’t often at the top of a traveler’s list. But that’s precisely why these cities need tourists. They might be not the most glamorous road trip destinations, but they represent America just as much, and maybe even more so, than others. The added bonus – they’re often cheaper when it comes to dining and accommodations. So hit the highway and go on an urban road trip to the post-industrial cities of the Midwest.

Start in Chicago and make the five hour drive to Detroit, swinging through Gary, Indiana, (where you can visit the King of Pop’s childhood home) or start directly in Detroit. One of the most notable examples of an industrial city with no industry left, Detroit has a reputation of being dirty, depressed, and dangerous. But look below the surface and you’ll find a community struggling to rise above.

Take in the city skyline on a Detroit River cruise, shop for fresh goods at the 100-year old Eastern Market, try your luck at one of the city’s casinos, wander the festive streets of the Greektown neighborhood, or head to nearby Dearborn to visit the Henry Ford Museum and learn about the history of the auto-industry in Detroit. For a total contrast, drive north from the city on Lake Shore drive and watch the crumbling abandoned buildings of Detroit give way to the majestic mansions of Grosse Pointe.

From Detroit, drive 3 hours to Cleveland, which – believe it or not – actually does kind of “rock”. Visit the A Christmas Story House, where everyone’s childhood-favorite Christmas movie was filmed. Check out the trendy new restaurants of the Warehouse District, sail the waters of Lake Erie, and shop one of the country’s largest indoor/outdoor markets, the West Side Market. And of course, you can’t forget the Rock and Roll Hall of Fame and Museum.

The 2-hour drive from Cleveland to Pittsburgh will take you past Youngstown, Ohio, another industrial town suffering in its post-industrial time. Pittsburgh itself was in much the same predicament not too long ago. Once known as “Steel City”, the city suffered massive layoffs and steel mill closures in the 1970’s and 1980’s and lost much of its population.

Pittsburgh invested in other industries and today is considered one of the most “livable” cities in the US, yet it still isn’t a very popular tourist destination, which it too bad as you’ll find plenty to do and see there. Visit the Andy Warhol Museum, check out theatre in the Cultural District, stroll the Victorian streets of the South Side Flats, or shop and dine at Southside Works or Station Square. The two entertainment complexes were converted from a former steel mill and a former train station and are a concrete example of how the city turned its faded industrial glory into a brighter future.

• Best time to make the trip: Late Spring to early Autumn
• Minimum days needed: 3

>> Book tickets to Chicago or check out things to do in Detroit

Overdone? Maybe, but with good reason. This is one of the most beautiful drives in the US, and travels through a wide variety of stunning scenery. If you drove straight through, city to city, on Highway 5, you could make the drive in about 14 hours. But why would you want to do that? If you stick to the coastal Highway 1 for the majority of the trip and plan on making several stops, you can do this trip quickly in 4-5 days or in 6-7 if you take a more leisurely pace.

Start in San Francisco and spend the first day driving past the winding cliffs along the ocean’s edge for about five hours to Mendocino. You can stay here or 10 miles north, in Fort Bragg. From here you can go whale watching (from December to April), deep sea fishing, or stroll the beautiful Mendocino Coast Botanical Gardens overlooking the sea. You can check out lighthouses, enjoy the beach, or drive inland for an hour and wander among the towering Redwood trees.

Continue on from there to Trinidad, California, about 5 hours north of Mendocino (though it you are feeling ambitious and are short on time, you could drive another 5-6 hours to Bandon, Oregon. In Trinidad, a small seaside town, you’ll find relaxation, natural beauty, and more access to the enormous Redwood trees of northern California. The small town of Bandon is known for its beautiful, rugged coastlines and unusual rock formations on the beach. Ride horses or search for crabs on the beach, or perfect your swing at one of the town’s three challenging courses.

From Bandon, it’s a 5 hour drive up to Cannon beach, or a bit farther to Astoria (the small town where you’ll find the house form the movie Goonies). Cannon Beach is home to Haystack Rock, a 235-foot tall rock formation just off the 4-mile long beach. It’s one of the largest “sea stacks” on the Pacific coast and the third largest monolith in the world. If you want to do more than hang out on the beach and check out rocks, you can also bird-watch, explore the nearby wetlands, or hike through several state parks. From there it’s just another 1-2 hours back to Portland, where you can enjoy tax-free shopping in the city or head out of town to explore the wineries of the Willamette Valley.

• Best time to make the trip: Spring and Autumn
• Minimum days needed: 4

>> Find flights to San Francisco or learn about wineries in Oregon

The drive from Miami to Key West, the most-southern part of the US, can be accomplished in about 3 hours with light traffic. But each of the Keys has its own flavor and attractions, and stopping once or twice along the way will give your trip a bit more variety. Even if you chose to spend all your days in Key West, it’s worth it to make the drive rather than fly direct. In addition to generally being cheaper, you’ll also have the chance to drive the unique Florida Oversea Highway, a 127.5-mile long section of Route 1 that connects the islands by several bridges that seem to stretch forever over the blue waters of the Atlantic.

The first key off of Florida, Key Largo is just east of the sprawling Everglades National Park. To the east of the island, you’ll find John Pennekamp Coral Reef State Park, home to the only living coral reef in the country, which makes Key Largo a popular diving and sport-fishing destination. Further south, you’ll pass Islamorada, composed of six keys.

Here you can swim with dolphins, hike through the lush foliage of Long Key State Park, scuba dive and fish. Marathon, a 10-mile long collection of islands and inlets, offers two of the few keys beaches at Bahia Honda State Park. There’s also a Dolphin Research Center, Turtle Hospital, and world-class wreck diving. Big Pine and the Lower Keys, just south of the Seven Mile Bridge, are often neglected and therefore usually quieter than some of the other keys. Kayak off the shores of the Lower Keys and you may see dolphins or several different types of sharks, or head to National Key Deer Refuge to see tiny native deer. Because of its undeveloped status, the Lower Keys area is home to more wildlife than any other key.

At the very southern end of the Oversea Highway, you’ll find the most-famous of the Florida Keys, Key West. Here it’s all about living the island life. Swimming in the crystal clear water around Fort Jefferson, drinking tropical libations and dining on fresh fish and conch. Visit the Southernmost Point in the Continental US, tour Ernest Hemmingway’s home and pet the local 6 or 7-toed cats that roam the island.

• Best time to make the trip: January to June
• Minimum days needed: 3

>> Find hotels in Miami or hotels in Key West

The terrain of the mid-Atlantic region, the central states along the eastern coast, can vary widely. From the flat, sandy beaches of the coast to the majestic blue mountains of Appalachia, to the gently rolling countryside of the old South, you can experience quite a bit in just a few days. Your choices for routes and itineraries are nearly unlimited. Stick to larger towns or retreat into rural areas. Hug the coast or venture further inland. Mix it up, chose a few locales and allot 3-5 days to cover north to south.

Start in Washington, DC and head south to Virginia, or land in Columbus, Ohio and journey about 2 east hours to West Virginia. In West Virginia, you’ll find awe-inspiring (or fear-inducing, depending on how you deal with heights) trestle bridges that span deep gorges covered in greenery. You can camp, hike, go white-water rafting, or explore the Appalachian Trial and the Blue Ridge Mountains. In Virginia, explore hundreds of wineries where you can tour and taste, wander the preserved colonial town of Williamsburg, or revel in the cuteness of the wild ponies of Assateague Island.

From Virginia or West Virginia, you can head south along the coast or through the inland rolling hills of North and South Carolina. Relax and soak up the sun on the coast near Myrtle Beach, South Carolina or learn to drive a race car at Dirt Track Racing School near Charlotte, North Carolina, both about 6 hours from various points in Virginia. From Charlotte to Charleston, South Carolina, it’s about 3 hours. Wander past pastel colonial houses on the cobbled brick streets of this genteel southern city and see the region’s history come alive at Boone Hall Plantation.

With an extra day or two, you can continue south for 3 hours to Savannah, Georgia, one of the most beautiful cities in the South. Tour the stately historical homes and lavish gardens of the city, wander among the eerily beautiful headstones at the Bonaventure Cemetery and dine on hearty Southern comfort food at restaurants like The Lady and Sons, owned by celebri-chef, Paula Deen.

• Best time to make the trip: Autumn through Spring
• Minimum days needed: 3

>> Book a flight to South Carolina or find hotels in Savannah

The central states of the US, those non-descript middle ones that always conjure images of endless corn fields and flat, boring land, are some of the best places to explore on a road trip. Yes, there will be long hours with not much to see, but it’s the perfect excuse to lose yourself in the joy of driving, belting out your favorite tunes and feeling the wind in your hair as you barrel down an empty road under the blue canopy of a wide open sky. There’s a lot of ground to cover here, so unless you plan on spending most of your time in the car or have several days, limit your route to one or two states.

In Iowa, explore small towns, follow one of the state’s five wine trails, hike, bike or canoe in the great outdoors, visit the Grant Wood Studio to see where the famous artist lived and worked, or drive one of the state’s eight Scenic Byways. The southern Historic Hills Scenic Byway takes you through Amish country and steamboat ports on the Des Moines River, while in the north the River Bluffs Scenic Byway winds alongside the Mississippi River past charming small towns. From Chicago, Iowa City is just 3 hours away.

Within around 3 hours drive from Iowa and Kansas, Nebraska has a reputation for being flat, boring and populated with mostly cattle. While there are plenty of wide-open spaces, and yes, lots of cows, there are also some beautiful sights to see in Nebraska as well. Scotts Bluff National Monument, a collection of large red rocks in west Nebraska, are quite dramatic, and the rolling expanses of the Sand Hills (which encompass nearly 20,000 square miles of sand dunes) are magnificent in their magnitude. Several scenic byways will take you past kitschy sites like “Carhenge”, a Stonehenge made of cars, or historic locales along the Lewis and Clark and Oregon Trails.

In Kansas, you can visit that most glorious of roadside attractions, the “largest ball of twine” or drive down the scenic 424-mile long I-70 highway across Kansas, stopping along the way at diners and monuments that evoke the spirit of the Old West and roadside America. Visit a 16-foot tall bronze sculpture of Buffalo Bill, the Kansas State Capital and the Moon Marble Company. There are also 9 scenic byways in Kansas. They pass through everything from cattle ranch country and prairie highlands to wetlands and salt marshes, bypassing bison, elk, waterfalls and small towns, and following some parts of the Lewis and Clark Trail.

• Best time to make the trip: Summer
• Minimum days needed: 3

>> Find flights to Kansas City or book a hotel in Nebraska

Running from Illinois to California, Route 66 is long, and much of it is unrecognizable as the road that inspired the song by Bobby Troup that urges “get your kicks on Route 66”. For the most impact in the shortest amount of time, pick up the road in Amarillo, Texas, about 6 hours from Dallas or 4 hours from Oklahoma City. Pass through downtown Amarillo, and then head through sprawling cattle country. Check out the “Grand Canyon of Texas” – the towering red rock formations of Palo Duro Canyon – and then head to the roadside attraction of Cadillac Ranch – a collection of dusty old Cadillac cars buried, nose-down in the sand.

From Amarillo, drive 4 hours or so to Santa Fe. Walk the touristy town square and shop for turquoise and art and enjoy some Mexican food and margaritas, or head out of town to one of the many nearby Pueblos for a look at traditional Native American culture. Just an hour up the road, you’ll find the small town of Taos, home to the Taos Pueblo, said to the oldest continually-inhabited settlement in the country. Tribal members still live here, without running water or electricity, as their ancestors did 1000 years ago. Visit the hot springs at Jemez Springs, explore the unusual formations at Tent Rocks National Monument, or spend a day in Albuquerque.

It’s around 5 hours from Albuquerque to Flagstaff, Arizona, with a stop in Winslow shortening that time by an hour. Here you’ll find a quaint small town, made famous by the Eagles hit “Take it Easy” with the line “Standin’ on a corner in Winslow, Arizona”. Other than nostalgia, visitors often come for the nearby Homolovi Ruins State Park and Clear Creek, a deep canyon filled with crystal clear water perfect for canoeing and swimming. Near Flagstaff, explore the ponderosa pine forest at Coconino National Forest, tour the lava trails around the Sunset Crater National Monument or drive just over an hour to the Grand Canyon.

• Best time to make the trip: Autumn to Spring
• Minimum days needed: 3

>> Find flights to New Mexico or learn about hiking in the Grand Canyon

Road trips don’t have to be endless adventures. There are nearly unlimited opportunities to explore America by car, and most can be done in a long weekend. So pack your bags, hit the road, and create your own unforgettable journey.

Read more about road trip travel and weekend getaways:

• Best American Train Trips for Under $100
• 7 Very Worthwhile Midwest Weekend Getaways
• 8 New Ideas for Summer Road Trips
  

Photo credits:
MaxyM , FloridaStock , Bill Ragan , Doug Meek , Bertl123 , Serge Skiba , science photo , Steve Rosset