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Fascinating Historic Driving Trails in the U.S.

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Are you a true U.S. history buff? Then you know that sometimes it’s not enough just to read about it — you have to get out there and experience history yourself. One of the best places to do just that is by following a historic driving trail, which will lead you through some of the most pivotal moments in American history. Hop in the car and see what you can learn along these eight fascinating historic trails from coast to coast.

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Frank Lloyd Wright Heritage Trail (Illinois and Wisconsin)

The high story Frank Lloyd Wright-designed S.C. Johnson and Son Inc. Research Tower.
Credit: Tribune Content Agency LLC/ Alamy Stock Photo

Frank Lloyd Wright fans have not one, but two options when it comes to driving trails that honor the groundbreaking architect: one in Wisconsin and one in Illinois. Wright was born in Wisconsin and lived in both states, so you can track a big portion of his life on these trails. In Illinois, you’ll drive to 13 sites, starting in Chicago at the Emil Bach House (the only property he designed in the city) before heading to his home and studio in Oak Park. After making your way to several other homes and a bank, you’ll finish at the Dana-Thomas House in Springfield, one of Wright’s most elaborate homes, with 35 rooms, more than 100 pieces of original furniture, and 250 art glass windows. The Wisconsin trail, which was made official in 2016, starts in Racine at the S.C. Johnson Research Tower, a 14-story design that’s one of only two existing Frank Lloyd Wright high-rises. From there, the drive takes you to four more sites (including Monona Terrace in Madison and Taliesin in Spring Green) before ending at the A.D. German Warehouse in Richland Center, the town where Wright was born.

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Harriet Tubman Underground Railroad Byway (Maryland to Pennsylvania)

View of the Harriet Tubman-Thomas Garrett statue in the Riverfront Park in Delaware.
Credit: EQRoy/ Alamy Stock Photo

Starting in Cambridge, Maryland, and stretching through Delaware to Philadelphia, the Harriet Tubman Underground Railroad Byway tracks Tubman’s remarkable life and escape from slavery in 1849. Tubman rescued at least 70 others from slavery along this route. Today’s historic drive has 45 stops, including the Pritchett Meredith Farm in Bucktown, Maryland, where a group of enslaved people on the path to freedom were betrayed and turned in by a Black farm owner; Tubman-Garrett Riverfront Park in Delaware, which overlooks the bridge where Tubman and a group of enslaved people evaded authorities by hiding under a load of bricks on a truck; and the last residence of Underground Railroad conductor William Still in Pittsburgh. Tubman eventually settled in the city, and Still helped support her and documented her trips to save other enslaved people.

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African American Heritage Trail of Martha’s Vineyard (Massachusetts)

View of houses and boats in Edgartown in Martha's Vineyard.
Credit: DenisTangneyJr/ iStock

The first four sites on the African American Heritage Trail of Martha’s Vineyard were dedicated in 1998. The trail was the brainchild of Carrie Camillo Tankard, vice-president of the NAACP chapter for the island of Martha’s Vineyard, and a local teacher, Elaine Cawley Weintraub. The two noticed a dearth of information about the contributions Black people made to Martha’s Vineyard throughout history, and decided to bring that history to the forefront. Today, the trail has 30 sites across every town on Martha’s Vineyard, all with bronze plaques explaining their significance. In Edgartown, for example, the trail highlights the homestead of William and Sarah Martin. In the 1850s, William became the first Black master of whaling ships on the island. Another stop on the trail, in the town of Vineyard Haven, marks the location of “Barber” Hammond’s shop, a Black-owned barber shop that opened in 1880.

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Blue and Gray Trail (Tennessee to Georgia)

View of downtown Chattanooga by Coolidge Park and the Market Street Bridge.
Credit: Kevin Ruck/ Shutterstock

Between Chattanooga, Tennessee, and Atlanta, Georgia, is a 120-mile stretch of land that saw some of the most significant events of the Civil War. The Blue and Gray Trail, which runs between the two cities, highlights 64 of these historic sites. One such site is Missionary Ridge in Tennessee, where Ulysses S. Grant’s forces won a battle that set the downfall of the Confederacy in motion. The trail also includes Pickett's Mill Battlefield Historic Site in Dallas, Georgia, one of the best-preserved Civil War battle sites. The trail is anchored by the Chattanooga National Cemetery on one end and the Margaret Mitchell House and Museum (where Gone With the Wind was written) at the other.

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Pony Express National Historic Trail (Missouri to California)

The Pony Express stables in St. Joseph, Missouri.
Credit: Americasroof/ CC BY-SA 2.5

When the Pony Express mail service was inaugurated in 1860, it reduced the time it took for messages to travel from Missouri to California (roughly 1,800 miles) to just 10 days — unprecedented for the time. Though the service was unprofitable and lasted just 18 months, the route is memorialized today in a driving trail, the Pony Express National Historic Trail. In Missouri, you’ll find Pike’s Peak Stable, purchased in 1860 to house the Pony Express’ horses. In Nevada, there’s Fort Churchill State Park, which contains the ruins of an adobe fort that was built to guard the route. And in Sacramento, California, the B.F. Hastings Building marks the end of the Pony Express.

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Route 66 (Illinois to California)

Close-up of a  Route 66 sign leading through Chicago, Illinois.
Credit: f11photo/ Shutterstock

Also called the Mother Road, Route 66 is America’s most famous highway. Built in 1926, it was the first highway to connect Chicago and Los Angeles. As more people traveled across the country by car, Route 66 became known for roadside kitsch — everything from wigwam hotels to giant roadside sculptures to mom-and-pop restaurants and shops. Today, the route strays a bit from what it was in its heyday, but you can still recreate a journey along much of the original Route 66 and see some of the historic Americana that remains.

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Oregon Trail (Missouri to Oregon)

Oregon Trail Interpretive Center near Baker City, showing an old wagon with a beautiful view.
Credit: Dan Lewis/ Shutterstock

Established in 1811, the Oregon Trail — heading from Missouri to Oregon — was initially used mainly by fur traders traveling on horse or foot. By 1836, though, the first wagon full of people struck out on the trail. It was a group of missionaries, but they didn't make it all the way to Oregon; they had to abandon their efforts about 200 miles shy of the trail’s end. The first people to travel the length of the trail were part of 1843’s Great Migration: a wagon train of about a thousand people that left Independence, Missouri, for an arduous five-month journey to Oregon. They set the wheels in motion for thousands more to head west. Today, you can drive along the trail and see remnants of what the pioneers left behind, including wagon ruts, signatures carved into rock, and a reconstructed fort.

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Texas Forts Trail

Entrance to the Presidio San Saba in Texas.
Credit: Diann Bayes/ Flickr/ CC BY-NC-ND 2.0

From 1848 to 1900, frontier forts popped up all over Texas, ordered by the U.S. Army for potential combat with frontiersmen and Native Americans. More than 100 temporary camps and 44 forts were constructed by soldiers during that period. Today, eight of those forts comprise the Texas Forts Trail, a 650-mile loop running through 29 counties in west-central Texas. Some forts, like Fort Phantom Hill, are nothing more than ruins, but others have been restored and are a gathering place for the community, like San Angelo’s Fort Concho. The trail also includes  a Spanish colonial presidio — Presidio San Luis de Las Amarillas, now known as Presidio San Saba.

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