Amazing Historic U.S. Trails You Can Still Travel

Chilkoot Trail

The Chilkoot Trail has amazing history. During the Klondike Gold Rush in the 1890's, men, women, and Children hiked the 33 miles from Dyea (a ghost town near Skagway), Alaska to Bennett, British Columbia, Canada, doing the best they could to get to the gold-fields. It was a trying journey up to the Chilkoot Pass. Coincidentally, if you haven't seen the old Disney (I think!) movie "Iron Will," they cover this crossing. Fun fact. Anyway, the trail became obsolete when a railway was built, but the trail still exists along with the camps and stops along the way. I have personally been through this area, starting in Skagway, and it's SO much fun. There are old cemeteries, ghost towns, stunning scenery, a great saloon, a haunted brothel, and so much more!

Length: 33 Miles Total
Permit & Booking Info


The Pony Express Trail


Most people have heard of the Pony Express, but just in case you haven't, this is the trail that strapping young boys would jump on ponies and deliver mail between Missouri and California starting in the 1850's. This adventure is the epitome of 'The Old West," with shootouts, evading Native American capture...or worse, deadly heat, exhaustion, robberies, and wildlife! After the riders would arrive in Sacramento, CA, the mail would be shipped to San Francisco where it could dispersed accordingly. Thousands of oxen and wagons has been crossing to Oregon and California via the Oregon Trail, but mail could be delivered much faster by light riders switching horses at various camps spread out through the western U.S. Today, the trail is established as a National Historic Trail, although traveling it in it's entirely would require you to get permission from different land owners since it spans so many modern states. However, you can access most of it, as well as each outpost and landmark, and can travel by car, hiking, horseback, or biking.

Nearest Town: St. Joseph, MO (start) or Sacramento, CA (end)
Length: 1840 miles
Plan Your Trip


The Trail of Tears

trail of tears historic trail

In 1830, Andrew Jackson signed a bill authorizing individual states to negotiate "fair" removal treaties with the Native Americans living on land that state governments wanted for white farmers and developers. It stated that Native Americans could not be forced to leave, but the government seemed to take the law as more of a suggestion, and many state governments supported this "Indian Removal Act," where "Indian Colonization Zones" were set up out west (to some mysterious land west of the Mississippi...apparently anywhere but where farmers wanted land). The result of this "treaty?" Choctaw, Chickasaw, Seminole, Creek and Cherokee people were driven from their lands without food, supplies, or help from the government in any way to the new "Indian Territory." Many had died from dehydration, exhaustion, disease, starvation, or violence. Keep in mind, too, there were OTHER Native Americans already on that land, so pushing sometimes-warring tribes together created new alliances and enemies among native people. By 1840, tens of thousands of Native Americans had been forcibly removed. 

Today the trail goes through Tennessee, North Carolina, Georgia, Alabama, Kentucky, Illinois, Arkansas, Missouri, and Oklahoma. You can hike much of the trail and there are numerous stops along the way, but there is not one starting point or end point, so it's a little tricky. The beauty of this is you can start anywhere and head west along a few different trails. Most start in Tennessee or Georgia.

Nearest Town: Chattanooga & Knoxville, TN, Rome, GA
Length: 2200 miles
Plan Your Trip


El Camino Real

el camino real trail

This gorgeous historic trail connects all 21 Spanish missions down the coast of California. The missions are all along the same route in California and were established by Las Californias Missionaries. The original route started in Baja California, Mexico, but when Mexico won its independence from Spain, the borders changed and technically, the first mission is now in present-day Mexico, not California. Mexican rancheros began traveling the same trails that native people and missionaries used up and down the coast and it became known as El Camino Real. The trail starts up in Northern California and meanders down the coast, sometimes along the California highways. It is not easy and sometimes the trail is not obvious or there at all, but it is not too challenging to to connect the missions. I have personally cycled some of these areas and you go through beautiful towns like Santa Barbara and San Juan Capistrano, where there is beautiful scenery, great food, and stuff to do! And please...don't forget to visit the beautiful missions!

Nearest Town: Sonoma, CA
Length: About 600 miles
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The Lewis & Clark Trail

Captain Merriwether Lewis and William Clark set out on an epic and harrowing journey in 1804 from St. Louis, MO to explore new lands acquired beyond the Mississippi River. Thomas Jefferson commissioned the two to find the most realistic and quickest water route to the end of the continent, collecting scientific data and sketches. Two years later, they returned with more than everyone bargained for and one hell of an adventurous story. Not many people know that the expedition did not only include Lewis and Clark, but a team of explorers that included a black man, a Frenchman, a Native American woman, a baby - all of which had equal votes in the day to day expedition decisions (minus the baby). The Native American was non other than the famous Sacagawea, who was ore of a badass than anyone else on the trip. In one instance, a canoe flipped over, littering supplies and people into the river, and she single-handedly rescued the supplies...and the men. She was the only one who could swim.

Because the trail itself traverses so many landscapes, including rivers, you may need to drive parts of it. However, the cities and landmarks themselves are very clearly marked and there are many stops along this lengthy route that make it obvious you are on the right path. Maps are in abundance!

Nearest Town: St. Louis, MO
Length: About 3700 miles
Plan Your Trip (GREAT Resource!)

The Oregon Trail


The stunningly beautiful and trying Oregon Trail can still be traveled with a decent amount of ease today. Leave around April-May, ideally, and start following the emigrants trail through Missouri, Nebraska, Kansas, Wyoming, Idaho Washington, and Oregon. There are many stops along the way and you can quite literally follow the wagon ruts still embedded in the ground. Hikers that have finished this trek, highly recommend camping over motels and absolutely stopping at every possible landmark along the way. Graves of original travelers can even be seen along the trail as you hike. Notable stops include Chimney Rock, Ash Hollow, Independence Rock (which has a rock with Oregon Trail names carved into it - super cool!), Sweet River Valley, and many highlights you will find in your old computer game. Please do not hunt and collect buffalo meat, and when crossing rivers, it's recommended you caulk the wagon and float unless you have a carpenter onboard. 

Nearest Town: St. Joseph, Missouri
Length: About 2000 miles
Plan Your Trip
Bonus Resource: Gregory Franzwa’s book, "The Oregon Trail Revisited"


Minuteman Bikeway

minuteman bikeway

This awesome and beautiful 10-mile bike path cuts right through the birthplace of the American Revolution. Paved in 1992, it follows along an old railway that from Cambridge to Bedford, MA that was the path that Paul Revere rode on his famous ride (you know..."One if by land, two if by sea"...). Pretty cool! It's really accessible from Boston at the Arlington/Alewife Station. See the maps and directions on how to follow this beautiful, historic trail!

Nearest Town: Boston, MA
Length: 10 Miles
Plan Your Trip


There are plenty of other notables, but some are either very short, turn into one of these I have already mentioned (i.e. The famous Mormon Trail, which turns into one of the forks of the Oregon Trail), or they are not navigable by foot, car, wagon, horse, or bike. Some of these are railroads.

Here are a few that may be of note but may fall into these categories:

  • Outlaw Trail, WY
  • Overland Trail, WY
  • Marietta Paper Mill, Sope Creek, GA
  • Apache Trail, AZ (drive) Plan Your Trip

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