Lincoln Highway East
Explore America’s first transcontinental highway from New York City to Chicago on a history-rich road trip.
Follow in the tyre tracks of early American motorists on this 14-night journey along the Lincoln Highway, the original coast-to-coast road that transformed American travel. Beginning in New York City and winding through New Jersey, Pennsylvania, Ohio, Indiana and Illinois, this route offers a nostalgic mix of Americana, charming small towns, rolling farmlands and remarkable national landmarks — all set against the backdrop of the USA’s earliest motoring heritage. With historic markers, original route alignments, vintage diners and reconstructed garages dotted throughout, the Lincoln Highway feels like stepping back to a golden age of road-tripping.
Along the way, discover Ivy League charm in Princeton, stand on the revolutionary streets of Philadelphia, explore Amish life in Intercourse, and walk the battlefield at Gettysburg. Continue west to the steel-city energy of Pittsburgh before crossing into the Midwest for classic American towns such as Mansfield, Lima and South Bend — home to the Studebaker legacy. Finish with two exciting nights in Chicago, the towering final chapter of your east-to-west Lincoln Highway adventure. This is a journey rich in heritage, culture and open-road freedom.
Remember: We’re UK-based, and every holiday we create is fully flexible – you can add nights, upgrade hotels, or enhance your itinerary. We love designing tailor-made self-drive adventures just for you!
14 night self drive holiday from £2,199pp including flights
Highlights
Drive the famous eastern section of the Lincoln Highway with historic markers and original 1910s alignments.
Explore Philadelphia, Gettysburg, Pittsburgh and Chicago — four of America’s great heritage cities.
Experience Amish Country in Intercourse, PA with farmland views and traditional crafts.
Visit key Lincoln Highway attractions including the Haines Shoe House, Soudersburg, Canton Palace Theatre, Studebaker Museum and more.
Your itinerary
Days 1–2: New York City
Skyscrapers, landmarks and the eastern gateway to the Lincoln Highway
Begin your holiday with the excitement of New York City before joining the historic route. Visit icons such as Times Square, the Empire State Building, and Central Park, or take a ferry to Ellis Island and the Statue of Liberty. NYC is where the original Lincoln Highway officially began before quickly shifting west into New Jersey. Enjoy world-class cuisine, museums and nightlife before your road trip begins in earnest.
2 Nights in
New York City, NY
Arrive &
Explore
Day 3: Princeton, New Jersey
Ivy League charm and early Lincoln Highway heritage
Travel south-west into New Jersey, following early Lincoln Highway alignments into the leafy university town of Princeton. Explore the stunning Princeton University campus, visit the Art Museum, or wander Nassau Street’s charming shops and cafés. This area was part of the first automotive “Good Roads” movement, helping shape what would become the Lincoln Highway.
1 Night in
Princeton, NJ
55 miles
Day 4: Philadelphia, Pennsylvania
Birthplace of American independence and classic early-highway stops
Arrive in Philadelphia, where America’s story began. Tour Independence Hall, the Liberty Bell, and the cobbled streets of Old City. The Lincoln Highway passed just north of here, marked by early automobile clubs promoting smoother, safer cross-state travel. Explore Reading Terminal Market, enjoy riverfront dining, or visit the Philadelphia Museum of Art — famous for the “Rocky Steps.”
1 Night in
Philadelphia, PA
45 miles
Day 5: Intercourse, Pennsylvania (1 night)
Amish Country, rolling farmland and Lincoln Highway Americana
Head west into Lancaster County, home of the Amish and a highlight of the eastern Lincoln Highway. Visit traditional craft shops, ride a horse-drawn buggy, or explore heritage sites such as the Lincoln Highway Experience Museum near Latrobe. Don’t miss quirky roadside Americana like the Haines Shoe House, a giant shoe-shaped home built in the 1940s along the Lincoln Highway route. Intercourse offers a peaceful, timeless charm and beautiful rural landscapes.
1 Night in
Intercourse, PA
60 miles
Day 6: Gettysburg, Pennsylvania
Scenic Amish Country, Civil War history and the road toward the Blue Ridge
Leave the peaceful farmlands of Intercourse and continue west along the historic Lincoln Highway, passing covered bridges, rolling fields and classic Americana. Arriving in Gettysburg, step into one of the most significant battlefields in US history. Explore Gettysburg National Military Park — whether by self-drive tour, licensed battlefield guide, or the excellent Museum & Visitor Center — and stand on sites such as Little Round Top and Pickett’s Charge. Wander the historic downtown filled with taverns, brick-front shops, and Civil War landmarks. This evening, enjoy Gettysburg’s atmospheric small-town charm and its deep connection to Lincoln himself, who delivered the iconic Gettysburg Address here in 1863.
1 Night in
Gettysburg, PA
50 miles
day 7: Chambersburg, Pennsylvania
Scenic Amish Country, Civil War history and the road toward the Blue Ridge
Your journey continues west to Chambersburg, a pivotal town at the crossroads of early American expansion, the Civil War, and the original Lincoln Highway. Explore its historic district, where 19th-century architecture lines walkable streets filled with cafés and independent shops. Visit the Chambersburg Heritage Center & Museum to learn how the town was burned during the Civil War and later rebuilt, or walk to Memorial Square, where US Presidents including Lincoln himself once passed through. Chambersburg also sits at the gateway to the scenic Michaux State Forest, offering opportunities for peaceful woodland drives or short hikes. Enjoy a relaxed evening in this charming, heritage-rich stop along America’s first coast-to-coast highway.
1 Night in
Chambersburg, PA
25 miles
Day 8: Pittsburgh, Pennsylvania
Steel City skylines, museums and Pennsylvania’s Lincoln Highway heritage
Follow the Lincoln Highway west through some of its most scenic and historic stretches. Your route climbs through the forested ridges of the Appalachian Mountains, passing classic roadside landmarks such as the restored 1930s Lincoln Highway Experience museum near Latrobe — a must-see stop showcasing period gas pumps, vintage billboards and the famous Banana Split sundae (invented nearby). Continue over Laurel Hill Summit, once one of the highway’s most challenging early crossings, before descending toward Pittsburgh, where three rivers meet beneath a dramatic skyline.
Arrive in Pittsburgh, a city transformed from its steel-mill heritage into a hub of culture, food and innovation. Explore the lively Strip District, visit the Andy Warhol Museum, or ride the historic Duquesne Incline for sweeping sunset views over the Golden Triangle. This evening, enjoy Pittsburgh’s mix of industrial history and modern energy before continuing your Lincoln Highway journey west.
1 Night in
Pittsburg, PA
155 miles
Day 9: Mansfield, Ohio
Ohio farmlands, small towns and early automotive history
Cross into Ohio on one of the best-preserved stretches of the eastern Lincoln Highway. Explore the classic American town of Mansfield, home to the Ohio State Reformatory (filming location for The Shawshank Redemption), charming main streets, and heritage sites celebrating the state’s road-building innovations. Enjoy local dining and a relaxed Midwestern atmosphere.
1 Night in
Mansfield, OH
160 miles
Day 10: Lima, Ohio
Vintage motoring heritage on the original 1913 alignment
Depart Pittsburgh and continue west along the historic Lincoln Highway, crossing into Ohio as the landscape softens into rolling farmland, classic small towns and nostalgic roadside Americana. This stretch offers a relaxed and scenic drive, echoing the golden age of cross-country motoring.
En route, pass through Mansfield where you can visit The Shawshank Redemption filming locations, including the striking Ohio State Reformatory, one of the film’s most iconic settings. Continue onward to Lima, a traditional Midwestern town with deep roots in America’s early automotive and oil industries. Settle in for the evening and enjoy the laid-back pace of small-town Ohio before your journey continues west. The region is dotted with restored 1920s service stations and brick-paved segments of the original road.
1 Night in
Lima, OH
65 miles
Day 11: South Bend, Indiana
Studebaker history and true Lincoln Highway atmosphere
Continue west into Indiana and arrive in South Bend, a must-see for anyone following the Lincoln Highway. Tour the Studebaker National Museum, celebrating one of America’s pioneering car manufacturers, and explore Notre Dame University’s iconic Golden Dome and basilica. The city played a key role in shaping early American motoring culture.
1 Night in
South Bend, IN
135 miles
Day 12: Naperville, Illinois
Charming suburbs on the approach to Chicago
Cross into Illinois and settle in Naperville, one of the state’s most welcoming suburban towns. Stroll along the Riverwalk, visit historic Naper Settlement, and enjoy lakeside dining. This area marks the final approach on the Lincoln Highway before reaching Chicago — a route that early drivers once travelled with excitement as they neared the Great Lakes metropolis.
1 Night in
Naperville, IL
95 miles
Days 13–14: Chicago, Illinois
Skyscrapers, lakefront icons and the western end of the Lincoln Highway
Arrive in Chicago, the famed western terminus of the Lincoln Highway and a spectacular finale to your east-to-west journey. Spend two unforgettable days exploring this world-class city — admire the skyline from the Willis Tower Skydeck, wander Millennium Park to see the reflective beauty of Cloud Gate, and enjoy an architectural river cruise that brings Chicago’s design legacy to life. Stroll along Navy Pier, browse the Art Institute’s remarkable collections, or shop the Magnificent Mile before dining on authentic deep-dish pizza.
On your final morning, enjoy a relaxed breakfast or a last walk along Lake Michigan’s waterfront before returning your car and heading to the airport for your flight back to the UK — bringing your epic Lincoln Highway East adventure to a memorable close.
2 Nights in
Chicago, IL
35 miles
May- Jun & Sept- Oct: Weather is likely to be pleasant for the entire trip. The midwest shouldn’t be too cold and the southwestern states shouldn’t be too hot.
We would expect maximum temperatures to be in the 20°C - 30°C range in the midwest and 25°C - 35°C in the south and southwestern states
Flight times to/from Chicago is around 8 hours and Los Angeles is approx 11 hours. You’ll drive through 3 time zones. Chicago is 5 hours and Los Angeles is 8 hours behind the UK.
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