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5 Epic Road Trips may seem like a lot for some people, but everyone needs to explore now and then. Whether you go with your family or on your own, each of these trips offers something unique. The United States highway system grew from a long history of intrepid and adventurous humans. Many of these paved highways today are the result of what were once ancient trails created by wild game, followed by American Indians, European explorers, colonists, traders, soldiers, and travelers slowly widening the narrow trails through woods or improving the easiest route over a mountain pass.

The modern interstate highway system we drive on may be the fastest route, but sometimes there isn’t much to see. Many of these 5 Epic Road Trips will require map reading skills. You will want to put away your Garman, Google maps, and whatever electronic device you prefer. Because, where we’re going, the internet is a little iffy and the accuracy of those maps is somewhat questionable. So grab your compass and smooth out those creases in your AAA or Rand McNally and let’s start exploring these 5 Epic Road Trips!

1. Kings Highway 

The oldest road in America goes by many names but its first name was Kings Highway. Before the Revolutionary War, the British crown funded a road connecting all the colonies from Boston, Massachusetts to Charleston, North Carolina. Construction began on the orders of King Charles II in 1650 and was completed in 1735. The network of ancient native paths, ferry routes, and wagon trails became connected, improved, and eventually extended northward into Maine and southward to Florida

Also called Pequot Path, Boston Post Road or Post Road, and a plethora of local names, Kings Highway reflects its importance. Riders delivered communications, handwritten letters, and vital newsprint to communities up and down the colonies. The road facilitated commerce and the transport of soldiers.

Over the years, areas of Kings Highway have been overlapped or paralleled by Main Streets, rail systems, other highways, and of course, the interstate system. At the end of 1926, the Bureau of Public Roads began the process of numbering the nation’s highways. But that’s not to say that Kings Highway has been obliterated. It hasn’t. In many cities along its route, it has been preserved or heralded.

The Northern Route

From Boston to New York, you’ll find historic markers and significant landmarks. One such marker recalls the Boston Massacre. Landmarks all along the Old Post Road remind us of all the historic figures who traveled the road including President George Washington, Alexander Hamilton, and Sarah Kemble Knight. The last one you might not be too familiar with, but the teacher and businesswoman wrote about her journey in humorous form back in 1704 and 1705, and her journal is still available to be read.

As you travel through the New England countryside and large cities, in some areas it might be difficult to identify Kings Highway. It is there, though, tucked in the colonial worlds it was built upon. From alehouses and inns in small towns like Lyme, Connecticut to familiar old histories like Wall Street, Kings Highway has evolved. In Brooklyn, we find it easily on a map, but then we must adjust and connect to New Jersey’s Route 27/US Route 206 before connecting to US Route 1 into the nation’s first temporary capital – Philadelphia. Make sure to see Kingston Bridge before leaving the Garden State, though.

Crossing the Mason Dixon Line

5 Epic Road Trips - Lewes, Delaware

Presbyterian Church on Kings Highway – Lewes, Deleware

Make time to stop in Lewes, Delaware at the historic Presbyterian Church on Kings Highway. The current church building was built in 1832, but the original congregation was organized in 1692 possibly before the road even reached it. Another reason to stop in Delaware is it might be the last time you hear Kings Highway for a while.

In Maryland, it is alternately known as Old Philadelphia Road, Pulaski Highway, US Route 1, MD 7, US Route 40, and sometimes, Old Post Road. While on these alternately named routes, take US 1 to Baltimore. The King’s Highway takes you within spitting distance (with a good wind) of Camden Yards and Babe Ruth’s old stomping grounds. I know you think I have my facts wrong, but I don’t. That same area is also home to Edgar Allen Poe, Francis Scott Key, and Fort McHenry among countless other worthwhile stops on your journey.

Keep connecting the highway dots until you make it to Charleston. There you will follow US Route 17 and sometimes Old Georgetown Road among others. And in many places, there is no road to follow, but there are plenty of markers and historians along the way to help you fill in the gaps.

One companion book to take with you as you make your journey would be The King’s Best Highway: The Lost History of the Old Post Road, The Route that Made America by Eric Jaffe.

2. Cumberland Road (National Highway)

If you’re going on one of these 5 Epic Road Trips, Cumberland Road should be one of them. In May 1806, for the first time in U.S. history, Congress appropriated federal funds for a road that would extend from Maryland to Ohio. They set aside $30,000 to build a road that would aid westward expansion and trade. It was a decision that President Thomas Jefferson championed, much like he championed the Corp of Discovery. A month after Congress signed off on the funds, the United States and France agreed to the terms of the Louisiana Purchase. Not only was the country growing in population, but it was also growing by acres. A year later, Captain Meriwether Lewis and Lieutenant William Clark led the expedition where no roads yet existed. 

Cumberland, Maryland is the starting point of the officially named National Road. Construction began in 1811 and eventually extended to Vandalia, Illinois. Our National Road has many things in common with Kings Highway, too. It started out as a toll road, but so did many roads in those days. Its names are as layered as the many layers used to build it and maintain it – National Turnpike, Cumberland Pike, National Highway, Main Street of American, and US Route 40. 

What to See
5 Epic Road Trips - Old Wheeling Suspension Bridge

Even so, unlike Kings Highway, it doesn’t do a disappearing act quite so often and is fairly well-maintained in the modern era of highways. From state to state, it is also well-marked. Along the route, history buffs will have ample opportunity to indulge in battle locations, historic buildings, and markers. Many styles and eras of architecture will greet you along the way, too. Homes with hexagon-shaped towers along the route are original tollhouses (no, Ruth Wakefield’s cookies weren’t made in a house that collected road tolls). You will also find markers called Madonna of the Trail. These statues represent the women pioneers who migrated west. Every state on the route has one as well as several points westward.

While in Pennsylvania, it’s worth mentioning a slight detour off of US Route 40 from Farmington to see two of Frank Lloyd Wright’s creations. You have to take Route 40 to get there anyway, so you might as well incorporate it into your trip. The first is Kentuck Knob and a few miles further is the magnificent Fallingwater. Bridges, such as Dunlap Creek Bridge in Pennsylvania and the Wheeling Suspension Bridge in West Virginia are worth a stop. Downtown Wheeling pops with colorful Victorian buildings before you enter Ohio.

From Wheeling to Zanesville, the National Road closely follows a route known as Zane’s Trace. Col. Ebenezer Zane began blazing the narrow military road westward along an existing trail in 1798. In the Hoosier State, you’re alternately greeted by historical elements of the National Road and those who lived along it. Two such personalities include the Hoosier poet James Whitcomb Riley and the World War II-era big band leader, Glenn Miller.

One particularly excellent guide to take with you as you drive Cumberland Road is Blue Highways by William Least Heat-Moon. He also travels on others described in 5 Epic Road Trips.

3. Lincoln Highway

The automobile made Americans and the world more mobile. We were venturing further from home and taking, for the first time, road trips. Once only an upper-class pleasure, these adventures prompted organizations to adopt highways and improve their quality. In 1912, Carl Fisher’s dream to build a road so people could drive their cars from coast to coast sounded much like Theodore Judah’s dream to create a transatlantic railroad. Fisher and his associates created the Lincoln Highway Association, planned a route, and began raising funds state to state. It was an enormous enterprise and without federal or state assistance, one that was never completed by the association.

Other auto associations formed with the intent of improving roads, but created chaos. Eventually, in 1926, when the Bureau of Public Roads began assigning numbers to sort out the chaos, many roads came under federal jurisdiction. The last stretch of Lincoln Highway was paved in 1935.

5 Epic Road Trips – Interstate vs U.S. Routes 
  • Signage – Interstates are numbered with a blue shield with a red top while U.S. Routes are typically a white numbered shield.
  • Speed limits – While speed limits vary state to state, interstate limits range between 50-80 miles per hour. Since U.S. Routes meander through towns and countryside, the speed limits not only have a wider range, they change frequently.
  • Access – Interstates restrict access to a limited number of points. However, they are well marked and are numbered based on the mile marker from the border of the state. For example, if you are traveling west and the exit is 15 miles west from the eastern border of the state, the exit will be exit 15. While traveling on U.S. Routes, the numbering isn’t always so logical. These highways directly access country roads, local communities, and interstate highways.

The original Lincoln Highway route stretches from Times Square in New York City and ends in Lincoln Park in San Francisco. You’ll travel through 14 states and several state capitals. A modern Lincoln Highway Association sprung up in 1992 and through their efforts an interactive map is available. It offers all the various routes, detours and marks the points of interest, too.

While you’re traveling cross country, pick up Jack Kerouac’s book On the Road or Brian Butko’s Greetings from the Lincoln Highway: America’s First Coast-To-Coast Road.

4. Will Rogers Highway or Route 66

Many personalities contribute to the pop culture phenomenon of Route 66. Will Rogers is one. The sharp-witted cowboy wrote a column in the Saturday Evening Post that made him a hometown hero to Cherokee Nation and Oklahoma. On a road trip in 1947, Bobby Troup wrote a song. Along for the ride was his wife Cynthia and Troup gives her the credit for “Get your kicks on Route 66.” You might remember Troup from the TV show Emergency! as Dr. Joe Early. Nat King Cole liked Troup’s song so well he recorded it and made it popular. And that’s why we get our kicks on Route 66.

A Little More History

Route 66’s history aligns with Lincoln Road. Auto associations with the intent of building decent roads were overwhelmed by the commitment and in 1926, the federal government came in to organize things, supply funding. Many of the roads involved with Route 66 had a long history like the Santa Fe Loop, Ozark Trail, and other trails of note. In fact, Route 66 connects to Lincoln Highway in Plainfield, Illinois, so if you’re looking for a way to check off a couple of boxes on your bucket list, Route 66 does it. The highway was completely paved in 1938.

John Steinbeck calls Route 66 “the Mother Road” in The Grapes of Wrath. He also revisits the open road in Travels with Charley: In Search of America.

The interstate highway system began encroaching on Route 66 in 1956, it took time, but in 1985 the old Mother Road was decommissioned. State by state, the highway fell into disrepair. Interstate 40, 44, and 55 replaced it. However, long stretches of Route 66 remain. And where you cannot travel on it, you can jump on the interstate until you can pick it up once again.

With so many things to see and do along the way, you will want to pick up a travel book. One option is The Best Hits on Route 66: 100 Essential Stops on the Mother Road by Amy Bizzarri. You can also check out travel blogs like the Post Card Jar. Their firsthand accounts will entertain and help you decide.

5. Old Highway 10
5 Epic Road Trips - North Dakota Sunflower

Our last of 5 Epic Road Trips takes a northern route along Highway 10. This historic byway connects Detroit, Michigan to Seattle, Washington. At various locations along its route, it is called Old Red Trail (North Dakota), Yellow Stone Trail (Montana), Mullan Road (Idaho), and Sunset Highway (Washington). It too is a relic left behind once the interstate system came through. Along most of its route, Interstate 94 draws traffic away from the meandering scenic route Highway 10 follows.

A lovely combination of urban and rural travel greets you on Highway 10. In Detroit, the QLine M-1 Rail runs along the old route. Stops in Ludington, Wisconsin, and pastoral landscapes take you the long way through the countryside.

You’ll Need a Map

Much of the internet will tell you that east-bound U.S. Route 10 ends at Fargo, North Dakota. But if you know where to look, you can find historic routes along the way. They detour through Main Streets in towns like Mandan, North Dakota where the home of the National Day Calendar operates. Points west take you to Theodore Roosevelt National Park and the North Dakota Badlands.

Through Montana, Idaho, and Washington the road can be spotty, but it is possible to pick it up here and there. Enjoy your travels through the Yellow Stone Trail and Old Sunset Highway. If you stop in North Bend, Washington, you might recognize Twede’s Cafe from the 1990s television show Twin Peaks.

Are you looking for more epic road trips? Check out the Pacific Coast Highway through California and Washington, The Oregon Trail from Missouri to Oregon, the Blues Highway from Nashville to New Orleans, and the Great Northern along U.S. Route 2.

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