Drive From Story to Story on These 13 Road Trips in the 13 Original Colonies

Follow paths once walked by Indigenous people, soldiers, enslaved Africans, and overshadowed women, from Georgia to New Hampshire.
Historic three-story buildings line Charleston downtown street, with palm trees on each side

Drive through layers of history in cities like Charleston.

Photo by f11photo/Shutterstock

The 13 original colonies of the United States—from New Hampshire to Georgia on the East Coast—are scattered with remnants of a revolutionary past. Mansions, monuments, battlefields, and walking trails all hold stories of Indigenous leaders, ghostly soldiers, enslaved people, and overshadowed women—but you would need to talk to tour guides to hear the tales told aloud.

Many of these sites are strung together on driving routes, like the Gullah Geechee Corridor in North Carolina and the Washington–Rochambeau National Historic trail from Rhode Island through Virginia. Here are 13 road trips, one for each of the colonies, where you can get a taste of all the complicated history and be inspired to dig deeper.

New Hampshire

Begin: Portsmouth
End: Hampton Falls

Three costumed re-enactors next to historic house bedecked with red, white, and blue bunting

The nonprofit Strawberry Banke educates the public with Native American artifacts as well as manuscripts and images from the 1600s onward.

Photo by James Kirkikis/Shutterstock

Start in historic Portsmouth with a Women of Portsmouth walking tour run by the Portsmouth Historical Society, and make sure to visit Strawbery Banke, an outdoor history museum featuring 1700s homes and 10,000–12,000-year-old artifacts from the Abenaki people. Then drive along the scenic waterfront of Portsmouth Avenue to Fort Constitution, which American colonists captured during the Revolutionary War, the day after Paul Revere’s ride. End your drive at the American Independence Museum in Exeter, where tours sometimes include beer and often talk about what independence means to all kinds of people in the country today. Then take the I-95 to Hampton Falls, where you can go apple picking at Applecrest Farm Orchards, which has been a farm since 1665 and got its current name in 1913.

Massachusetts

Start: Concord
End: Boston

 "Turret Tops" sculpture (by Leeza Meksin): two large, pink, tepee-like structures among trees

The outdoor artwork regularly changes at the deCordova Sculpture Park.

Photo by Yingna Cai/Shutterstock

Pass verdant forests along the Battle Road Trail, which follows a Revolutionary battlefield for five miles. Then drive your way over to North Bridge, site of the infamous “shot heard round the world.” Put that moment into context at the Concord Museum, which covers everything from Paul Revere’s lantern to contemporary Indigenous textile traditions. Detour to Lincoln for the deCordova Sculpture Park and Lexington for Lexington Battle Green, where the war started. Wind up your drive at the Boston Tea Party Ships & Museum, where you can throw bags of tea into the harbor. Stick around town to explore the Boston Women’s Heritage Trail, a collection of more than 100 sites that showcase the achievements of of suffragettes and abolitionists; self-guided and private tours are available.

Rhode Island

Start: North Smithfield
End: Wickford

Drive along Route 102 for Slatersville, a preserved mill village in North Smithfield from 1807; Burrillville, the farmhouse that inspired the horror film The Conjuring; and Exeter for vampire lore at Chestnut Hill Baptist Church cemetery. End in the coastal village of Wickford, which has classic harbor views and the Smith’s Castle house museum. The property highlights the history of Cocumscussoc (the original name of the area, homeland of the Narragansett people, and a National Historic Landmark) and focuses on public education about enslaved people (part of the Rhode Island Slave History Medallion program).

Connecticut

Start: Stonington Borough
End: New Haven

 Couple on bench facing foggy harbor of small boats

People have been admiring sailboats in Stonington for hundreds of years.

Photo by TheBrassGlass/Shutterstock

Admire bobbing sailboats en route to Historic Stonington harbor, which were once led to safety by the 1840 stone lighthouse that visitors can still climb . Ten minutes away is Mystic and its respected century-old Seaport Museum, which has more than 500 ships and a preservation shipyard, plus a re-creation of a 19th-century maritime village. Once in New Haven, make your way to the sculpture honoring the 1839 Amistad rebellion of enslaved people, and spend time on the Connecticut Women’s Hall of Fame heritage trail.

New York

Start: Geneva
End: Skaneateles

Sunrise on Lake Cayuga with pier, viewed from shore

Route 20 passes Lake Cayuga in the Finger Lakes region of New York.

Photo by Michael Shake/Shutterstock

At 3,365 miles, Historic Route 20 is the longest highway in the country, connecting the East and West coasts from Massachusetts to Oregon. The New York section passes through the vineyard-filled Finger Lakes region. Start in Geneva, once a major Seneca Nation village called Kanadesaga that was destroyed in 1779 by a military campaign in the Revolutionary War. Stop in Seneca Falls to visit the National Women’s Hall of Fame. Then take an estate tour of Auburn, Harriet Tubman’s chosen home. End in the lakefront town of Skaneateles and nearby Carpenter Falls in the Bahar Nature Preserve.

Sponsored by the Arizona Office of Tourism
Travel back through time on Route 66, a quintessential part of American history and culture that’s turning 100 this year. No matter which direction you’re headed, there are plenty of picture-worthy stops, from the Rainbow Rock Shop in Holbrook to the retro vibe in Williams.

New Jersey

Start: Frenchtown
End: Trenton

Local historian and author Rick Epstein runs walking tours in Frenchtown that cover topics like a Civil War hero, a curious alligator tale, and several deaths. Afterward, drive Route 29, a National Scenic Byway along the Delaware River. Pull over in Lambertville for art galleries and the Historical Society building that once served as Washington’s headquarters. Continue onward to Washington Crossing State Park, where the future president famously crossed the Delaware River to win the Battle of Trenton against the British. In Trenton itself, 1719 William Trent House Museum uses guided tours and events to share stories about the house, its inhabitants, and people of the area, including displaced Indigenous people, enslaved people, and freed African Americans.

Pennsylvania

Start: Philadelphia
End: Chester

Dancers on stage with Kwanzaa candles at edge, plus several drummers in front of audience

The African American Museum in Philadelphia has events and celebrations all year.

Photo by J. Fusco/Visit Philadelphia

Philadelphia is chock-full of history. You could take a Constitutional Walking Tour, or admire the English architecture while walking around Old City and Elfreth’s Alley, but make sure to spend time at the African American Museum or hear about women and Indigenous and Black people at the Museum of the American Revolution. Stop by the American Swedish Historical Museum before leaving the city, then hop on I-95 to Chester, the oldest town in the state. End your trip with a visit to Brandywine Battlefield for exhibits, tours, and events that recount the longest, largest battle in the American Revolution.

Delaware

Start: Wilmington
End: New Castle

Begin in the Brandywine Village neighborhood of Wilmington, where a monument marks Delaware’s section of the Washington–Rochambeau National Historic Trail. The 680-mile land and water route extends through nine states, following the path marched by American and French soldiers on their way to the Battle of Yorktown, which they won decisively in 1781. Another key revolutionary spot along the route is the Hale–Byrnes House, where General Washington held council for an earlier confrontation with the British, the Battle of the Brandywine in 1777. Last stop: the New Castle Court House Museum, where the state first declared its independence from Britain and from Pennsylvania in 1776.

Maryland

Start: Elkton
End: Annapolis

The town of Elk Landing became an important transportation and supply hub during the Revolutionary War. Today, visitors can wander the grounds, gardens, and two historic houses at the Historic Elk Landing Site to learn about the area’s role in the war, including the genius of enslaved woman Hetty Boulden, who saved the town by leading an invading British troop away from the property. Then drive on I-95 to Jerusalem Mill Village, an 18th-century mill turned into a living museum with reenactments and storytelling. Continue to Baltimore for a visit to Fort McHenry, where the defense of the fort inspired Francis Scott Key to pen the national anthem. Then drive south on I-97 to the Historic London Town and Gardens in Annapolis for an exhibit on the Piscataway people to Jonas and Anne Catharine Green House, to learn about Anne, who used her position as head of the Maryland Gazette to spread the idea of independence in the 1760s

Virginia

Start: Yorktown
End: Jamestown

Group of soldiers firing muskets in field: a re-enactment of the battle at Yorktown

You can find regular re-enactments in Yorktown, since the battle here was a pivotal moment in the Revolutionary War.

Photo by Joseph Sohm/Shutterstock

Watch a short film about the siege of Yorktown at the American Revolution Museum, then stop by the Yorktown Battlefield to see where the turning-point victory took place. Take a scenic drive along the York River on Colonial Parkway and through the marshlands of Colonial National Historical Park. When you get to Williamsburg, spend time at the Colonial Williamsburg: This is a living museum with costumed re-enactors who know their stuff; it has expanded over the years to include Black life, women, and Indigenous people. Finish in Jamestown, the site of the first permanent English colony in North America. The Jamestown Settlement Museum has more re-creations (ships, an 18th-century farm, a Continental Army encampment) and weaves stories of the settlers, Indigenous peoples, and Africans of the time. The Jamestown Glasshouse, part of Colonial National Historical Park, is the oldest glassblowing manufacturer in the country.

North Carolina

Start: Wilmington
End: Edenton

Exterior of two-story brick Bradham's Pharmacy, the birthplace of Pepsi-Cola (L); two hands holding bottles of the drink (R)

Founded in 1710, New Bern has witnessed more than the Revolutionary War.

Photo by danf0505/Shutterstock (L); photo by emma valerio/Unsplash (R)

Wilmington is located along the Gullah Geechee Heritage Corridor, celebrating the heritage of an African American community that retained much of the culture and arts (like music and basket weaving) from West Africa. Explore Airlie Gardens for guided history tours among the flowers. Then get on U.S. Route 17 to New Bern, where you can visit the birthplace of Pepsi and scout for fiberglass bears, created for the 300th anniversary of the city’s founding. In Edenton, take a Historic Edenton Trolley Tour to see the architecture and monuments over the centuries.

South Carolina

Start: Gaffney
End: Charleston

Begin your road trip at Cowpens National Battlefield, a 1781 Revolutionary War site where a victory for the Continental Army led to a turning point in the war. Then drive southeast to the Ninety Six National Historic Site, named by 16th-century traders for its distance to a Cherokee village. The site—and its aptly named Star Fort—became a British Loyalist stronghold in the Revolutionary War, but the American troops laid the longest siege of the war there in 1781. When you reach Charleston, dig into the country’s Black history; it’s estimated that some 90 percent of Black Americans have at least one ancestor who arrived in Charleston’s ports. Today, you can learn their stories at the Old Slave Mart Museum, the first museum about slavery in the United States, and at the much newer International African American Museum, a must-see destination that opened in 2023. You can also experience it in the thriving culinary scene of the Gullah Geechee culture, descendants of enslaved West African who are making some of the best food in the city.

Georgia

Start: Atlanta
End: Savannah

Bonaventure Cemetery in Savannah, with large trees draped in moss

Bonaventure is Savannah’s oldest cemetery, full of historic memorials.

Photo by Atomazul/Shutterstock

In Atlanta, visit the APEX museum in the Sweet Auburn Historic District, which was home to a wealthy Black community in the early 1900s; the area includes the birthplace of Dr. Martin Luther King Jr. and is now speckled with Civil Rights markers. Then take I-75 S and I-16 E, passing the Piedmont National Wildlife Refuge in Hillsboro, mansions in Madison, and Ocmulgee Mounds National Historical Park in Macon, a prehistoric Indigenous site. Savannah is renowned for its haunting atmosphere, so once you arrive, be sure to check out the Victorian-inspired Bonaventure Cemetery. You can also hear more about the Gullah Geechee culture at Pin Point Heritage Museum, located in an oyster and crab factory from 1926.

Kemi Ibeh is a freelance travel writer in New York City with a niche in destination itineraries, history, and culture. She writes on New York experiences, travel trends, and interesting history in various locations. She lives in Brooklyn, runs a travel blog called Musings and Adventures, and loves weekend getaways to walkable cities with interesting Main Streets.
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