The Great American Music, Heritage and Route 66 Trail

Welcome to Cleveland, the city where rock & roll found its rhythm. After arriving at Cleveland Hopkins International Airport, transfer independently to your downtown hotel. With your arrival likely in the late afternoon, keep your first evening easy — perhaps enjoy a relaxed dinner along East 4th Street, Cleveland’s lively dining hub, or take a sunset stroll by Voinovich Bicentennial Park, where the shimmering waters of Lake Erie frame the skyline.

Today is all about discovering why Cleveland rocks. Your included admission to the Rock & Roll Hall of Fame offers an immersive journey through the history of popular music — from Elvis to The Beatles and modern icons. Explore the museum’s seven floors of interactive exhibits, rare instruments, and iconic costumes.

Afterwards, head next door to the Great Lakes Science Center or wander the waterfront paths. Later, explore University Circle, home to the Cleveland Museum of Art and the Cleveland Botanical Garden. In the evening, dine riverside in The Flats, where live music, creative cuisine, and a relaxed, welcoming vibe capture Cleveland’s heart.

Spend your final full day in Cleveland exploring its rich mix of culture and outdoor beauty. Begin at the West Side Market, one of the country’s oldest indoor markets, offering everything from artisan pastries to pierogis. Then, explore the Cleveland Metroparks, known as the “Emerald Necklace,” a network of scenic trails, rivers, and green spaces encircling the city.

If you’re visiting during baseball season, catch the Cleveland Guardians in action at Progressive Field — a quintessential American experience. For dinner, head back downtown or try one of Ohio City’s craft breweries for a local beer and hearty Midwest fare.

This morning, pick up your rental vehicle and journey northwest to Detroit (approx. 3 hours), a city with a proud industrial past and a creative spirit that never faded. Upon arrival, check into your hotel and enjoy a relaxed afternoon exploring Campus Martius Park or the Detroit Riverwalk, one of America’s most scenic urban waterfronts.

In the evening, embrace Detroit’s culinary scene — perhaps try a meal at The Apparatus Room or explore the city’s thriving music bars, where Motown and modern soul still fill the air.

Discover Detroit’s legendary contribution to music and American culture today. Begin at Hitsville U.S.A., the Motown Museum, where The Supremes, Stevie Wonder, and The Temptations recorded their greatest hits. Continue to the Detroit Institute of Arts, home to world-class collections including Diego Rivera’s “Detroit Industry” murals.

After lunch, visit the Eastern Market or stroll through revitalised neighbourhoods like Corktown and Midtown, filled with independent shops and street art. As evening arrives, enjoy dinner and perhaps some live jazz or blues — the perfect tribute to this city of rhythm and reinvention.

Depart Detroit and make your way to Chicago, the Windy City (approx. 4½ hours). Along the route, consider stopping at Ann Arbor or Indiana Dunes National Park for a scenic break. Upon arrival, return your rental car and settle into your downtown hotel.

Spend the evening unwinding with dinner at Navy Pier or take a relaxed stroll along the Chicago Riverwalk, where glittering skyscrapers and waterfront restaurants create the perfect first impression of this iconic city.

Today, use your included Hop-On-Hop-Off Sightseeing Bus Tour to explore the best of Chicago at your own pace. Take in highlights like the Willis Tower Skydeck, Millennium Park, and The Art Institute of Chicago. Stop at Adams Street, where Historic Route 66 officially begins — the perfect photo opportunity before your onward adventure.

In the evening, experience Chicago’s legendary music scene with a live blues or jazz performance at Buddy Guy’s Legends or Green Mill Cocktail Lounge, both steeped in history and atmosphere.

This morning, pick up your rental car and hit the open road, joining Historic Route 66, the “Mother Road.” The drive to Springfield (approx. 3½ hours) takes you through stretches of classic Americana — vintage diners, quirky roadside stops, and nostalgic charm.

Upon arrival, visit the Abraham Lincoln Presidential Library and Museum to explore the life and legacy of America’s 16th president. In the evening, enjoy a hearty Midwest dinner and reflect on your journey so far.

Continue your Route 66 adventure today as you drive south to St. Louis (approx. 2 hours), known as the Gateway to the West. Along the way, enjoy glimpses of classic Americana — roadside diners, vintage gas stations, and nostalgic Route 66 icons that capture the spirit of the open road. Upon arrival, check into your hotel and spend the afternoon at leisure exploring the vibrant downtown area. Take a stroll through Laclede’s Landing along the riverfront or unwind in the Central West End, where cafés and boutique shops line the leafy streets.

As evening falls, head to the Soulard District, one of St. Louis’s oldest and most atmospheric neighbourhoods. Known for its live music, welcoming taverns, and world-famous BBQ, this lively area is the perfect place to experience the city’s soulful charm and Southern hospitality.

Today, experience the best of St. Louis on your included City Tour, which includes admission to the Gateway Arch — the tallest monument in the United States and an enduring symbol of the American frontier. Enjoy breathtaking views from the top before setting off on a scenic Mississippi River Cruise, offering a unique perspective of the city’s skyline and historic waterfront.

Later, spend time in Forest Park, one of the largest urban parks in the country and home to free attractions including the St. Louis Art Museum, St. Louis Zoo, and Missouri History Museum. To continue your Route 66 journey, make a stop at the Museum of Transportation, where vintage cars, trolleys, and locomotives tell the story of America’s travel heritage.

No trip to St. Louis would be complete without a visit to Ted Drewes Frozen Custard, a beloved Route 66 institution that has been delighting travellers since the 1920s. Try one of their famous “concretes” — so thick you can turn them upside down — before heading out for a final evening of live jazz or blues, celebrating St. Louis’s enduring musical legacy.

Depart St. Louis for Indianapolis (approx. 4½ hours). Once you arrive, check into your hotel and explore Monument Circle, the heart of the city. Later, head to the Indianapolis Canal Walk, where gondolas glide past cafes and public art installations. Enjoy a relaxed dinner at one of the nearby restaurants and soak in the city’s welcoming atmosphere.

Spend the day exploring Indianapolis’s unique blend of sports heritage and cultural attractions. Visit the Indianapolis Motor Speedway Museum, where you can learn about the legendary Indy 500, or explore the Mass Ave Arts District, filled with boutiques, galleries, and eateries.

If time allows, take a short trip to the White River State Park, home to the Eiteljorg Museum of American Indians and Western Art, for a taste of Midwest culture.

Today’s drive takes you to Cincinnati (approx. 2 hours), a city that beautifully blends historic architecture with modern flair. Upon arrival, check into your downtown hotel and explore the Over-the-Rhine District, known for its 19th-century buildings and craft breweries.

Enjoy dinner at The Banks, where riverfront restaurants overlook the John A. Roebling Suspension Bridge — one of the most picturesque evening spots in the Midwest.

On your final full day, explore Cincinnati’s highlights. Visit the Cincinnati Museum Center at Union Terminal, an Art Deco landmark, or learn about the city’s powerful past at the National Underground Railroad Freedom Center. For something lighter, take a walk through Smale Riverfront Park or ride the Cincinnati Observation Wheel for panoramic views of the Ohio River.

In the evening, enjoy your farewell dinner in the lively Over-the-Rhine neighbourhood or catch a baseball game at Great American Ball Park, home of the Cincinnati Reds.

After breakfast, your Great American Music, Heritage & Route 66 Trail journey comes to an end. Depending on your flight schedule, you may have time for one final stroll through downtown Cincinnati or a visit to Findlay Market, the city’s beloved historic marketplace filled with local flavours and artisanal treats, before transferring independently to the airport for your flight home.

If you have more time to devote to your adventure, consider extending your journey. Options include travelling south into Kentucky — perhaps to explore the Bourbon Trail or the scenic Bluegrass countryside — or looping back north to Cleveland via Columbus, completing your circuit through the heart of America’s Midwest.

Speak with your Discover North America Travel Specialist to tailor an extension that perfectly suits your interests, ensuring your road trip ends on a note as unforgettable as it began.