5 Fantastic American Road Trips for Music Lovers

Few experiences can rival a leisurely, music-themed road trip for soaking up the soundtrack of America. With the windows down (or the convertible top open) and your favorite hits playing, you'll truly enjoy the journey. While cities like Nashville, New York, and New Orleans are celebrated for their rich musical heritage, it's in the small towns that you'll find the juke joints and honky-tonks, as well as the farms and rural recording studios where legends refined their craft and pioneered new styles. Prepare your playlist and get set to hit the road.

Experience the Blues in the Mississippi Delta

• Start: Tunica, Mississippi
• End: Vicksburg, Mississippi
• Distance: Approximately 180 miles
• Recommended Duration: Two to three days

Memphis is a prominent blues center, but true fans know a pilgrimage to the genre's roots in the Mississippi Delta is essential. Highway 61 stretches through the flat, fertile fields and historic farming towns that gave rise to legends like Muddy Waters and B.B. King, earning the Delta its reputation as “the Most Southern Place on Earth.”

Start your journey at the Gateway to the Blues Museum, located in Tunica’s historic 1890s train depot, close to Robert Johnson's childhood home. From there, head to Clarksdale, where legend has it he sold his soul to the devil at the Crossroads. Although the exact spot is debated, a well-known Crossroads Monument marks the intersection of Highways 61 and 49. After exploring the Delta Blues Museum, dive into Southern sounds at the Morgan Freeman-owned Ground Zero Blues Club or the cash-only juke joint Red’s Lounge, then settle in at the Travelers Hotel. Originally a modest stopover for railroad workers in the 1920s, it has been transformed into a shabby-chic boutique hotel adorned with quilts and artwork from local Mississippi artists.

As you drive south, each town unveils a new part of the blues narrative. Rural Cleveland hosts the Grammy Museum Mississippi (home to more Grammy winners per capita than anywhere else in the USA) and Dockery Farms, a historic cotton gin where blues legends like Howlin’ Wolf and Willie Brown crafted their songs. Grab some hot tamales (a Delta delicacy) at Airport Grocery and detour to visit the gravesite of Robert Johnson in Greenwood and the birthplace of B.B. King in Berclair, just 15 miles away, before exploring a museum dedicated to King in nearby Indianola. Back on Highway 61, Leland features its own scrappy Highway 61 Blues Museum, a worthwhile stop before concluding your trip in Vicksburg. This riverside city, known as the birthplace of Willie Dixon, now buzzes with riverboat casinos and restaurants like 10 South Rooftop Bar & Grill, offering stunning views of the Mississippi River and the Yazoo Canal.

Celebrate the Summer of Love along California Highway 1

• Start: San Francisco, California
• End: Big Sur, California
• Distance: Approximately 150 miles
• Recommended time: Two to three days

Embrace your inner flower child on a ’60s-inspired road trip beginning in San Francisco. A morning walk through Golden Gate Park will transport you back to the Human Be-In that unofficially ignited the Summer of Love in 1967. However, the true essence can be found in the vibrant Haight-Ashbury, where the tunes of Janis Joplin, Jefferson Airplane, and the Grateful Dead once filled the air. Don’t forget to grab some albums at the expansive Amoeba Music, a treasure trove for music lovers that feels like a cathedral dedicated to pop culture. In the evening, check out the lineup at the Fillmore, a historic venue where the Dead performed 51 shows in the late ’60s.

On day two, rise early at the eclectic Hotel Zeppelin and embark on your journey south along Highway 1. Make a stop at the Grateful Dead Archive at UC Santa Cruz before heading to Monterey, the birthplace of the Monterey International Pop Festival, which inspired Woodstock. Explore record shops like Recycled Records, which has been around since 1975, and Siren Records Monterey, dedicated to new vinyl, CDs, and cassettes.

Further along the coast in Big Sur, visit the Henry Miller Memorial Library, honoring the often-banned author of Tropic of Cancer. This cultural hub hosts occasional live music events, featuring artists like David Crosby and the Red Hot Chili Peppers. Conclude your journey with a mindful experience at Esalen, a retreat center offering wellness workshops where icons like George Harrison, Mama Cass Elliot, Joni Mitchell, and Joan Baez sought spiritual awakening on these rugged cliffs.

Celebrate folk legends in New York

• Start: New York City
• End: West Saugerties, New York
• Distance: Approximately 175 miles
• Recommended time: Two to three days

Kick off your homage to the 1960s folk scene in Bob Dylan’s Greenwich Village. Recreate the iconic album cover of The Freewheelin’ Bob Dylan by snapping a picture at the corner of Jones Street and West Fourth Street. Catch a performance at his former haunts, like the Bitter End, where Joan Baez and Joni Mitchell once graced the stage, or Café Wha?, the venue where Dylan played on his first night in the city after hitchhiking from Minnesota in January 1961. Spend the night at the recently renovated Hotel Chelsea, a historic establishment from the 1880s that has hosted the likes of Patti Smith and Leonard Cohen. Now featuring a stylish lobby bar and the revived Spanish restaurant El Quijote, the hotel has shed its notorious past, including being the site where Sid Vicious allegedly killed Nancy Spungen.

On the following morning, head upstate to Bethel Woods Center for the Arts, a venue and museum located at the original site of the 1969 Woodstock Music & Art Fair, which was once Max Yasgur’s dairy farm. This year, new camping options are available, including a glamping experience with in-tent bathrooms. If camping isn’t your style, take a scenic route east through the Catskills toward Woodstock. Try to catch a performance at the inviting Levon Helm Studios, an acoustically designed barn created by the legendary drummer, where his family continues the tradition of his famous Midnight Rambles. For an overnight stay, there’s no better choice than Big Pink, the modest house in West Saugerties where Dylan and The Band recorded The Basement Tapes.

Set off on a greatest hits road trip through Tennessee

• Start: Memphis, Tennessee
• End: Bristol, Tennessee
• Distance: Approximately 500 miles
• Recommended time: Five to seven days

Despite being the 36th largest state in terms of area and the 15th by population, Tennessee has consistently made a significant musical impact. This eastward route begins in Memphis, offering you a chance to craft your own experience: explore rock history with visits to Sun Studio and Graceland, enjoy blues music on Beale Street, or delve into the soul at the Stax Museum of American Soul. Travel about 60 miles east to Brownsville’s West Tennessee Delta Heritage Center, located in the very one-room schoolhouse attended by Anna Mae Bullock (later known as Tina Turner), now featuring her memorabilia—the only museum dedicated to Tina Turner in the world.

Kick off the country segment of your journey by visiting the site in Camden (85 miles further east) where Patsy Cline tragically lost her life in a plane crash in 1963. After that, take a 40-minute drive to Loretta Lynn’s Ranch in Hurricane Mills for a guided tour. Once you reach Nashville, you could spend a day, a week, or even a month and still not experience all the highlights: Country Music Hall of Fame and Museum, National Museum of African American Music, Ryman Auditorium, and the Bluebird Café. On the northeastern edge of the city, don't miss a backstage tour at the Grand Ole Opry and consider staying overnight at the nearby Gaylord Opryland Resort & Convention Center.

As you venture into the Appalachian region of the state, conclude your trip in true southern fashion at Dollywood in Pigeon Forge, which is introducing a new Dolly Parton Experience this spring that showcases her achievements as a songwriter, fashion icon, and philanthropist. If you don't take the time to relax at her new HeartSong Lodge & Resort, continue to where it all began: Bristol, Tennessee, located on the Virginia border, is home to the Smithsonian-affiliated Birthplace of Country Music Museum. This museum narrates the history of the pivotal 1927 recording sessions regarded as the “big bang” of country music.

Embark on a three-city tour across the Midwest

• Start: Cleveland, Ohio
• End: Chicago, Illinois
• Distance: Approximately 450 miles
• Recommended time: At least four days

The shores of the Great Lakes and the Rust Belt cities surrounding them have been pivotal in musical innovation. Start your Midwest journey in Cleveland, home to the Rock & Roll Hall of Fame, now featuring a new exhibit celebrating 2023 inductees such as Missy Elliott, Willie Nelson, Chaka Khan, and Rage Against the Machine. Cleveland earned this honor thanks to DJ Alan Freed, who championed the new genre and broke racial barriers in the 1950s. Pay tribute to his legacy by visiting his jukebox-shaped grave in Lake View Cemetery.

Head west along I-90, veering north at Toledo to reach Detroit, where the Motown Museum is set for a multi-million-dollar renovation and expansion. This museum houses Hitsville U.S.A., the first headquarters of the iconic record label, in a white house on West Grand Boulevard purchased by founder Berry Gordy in 1959. Enjoy a meal at the Black-owned Waffle Cafe on Livernois Avenue, and don’t miss the Motown mural by artist Fel’le, showcasing legends like Smokey Robinson, the Temptations, and the Supremes.

Continue your journey through Michigan and arrive in the Windy City. Chicago boasts a rich musical heritage, from blues and gospel to modern jazz, but it also holds a special place in the hearts of Gen X-ers and elder Millennials for its indie rock scene, being home to both Lollapalooza and Pitchfork Music Festival. Snap a photo of the iconic Marina City towers, featured on the cover of Wilco’s Yankee Hotel Foxtrot; grab a pint at the Rainbo Club, where Liz Phair shot her Exile in Guyville album cover; and check out performances at the Empty Bottle, Lincoln Hall, Riviera Theatre, or the Metro. For a classic finish, unwind at the Green Mill Cocktail Lounge, a bebop and free jazz venue frequented by Al Capone. Though not the most luxurious, Hotel Versey is rich in rock history; formerly known as the Rock and Roll Days Inn, it has hosted legends like Greg Allman, Nirvana, and Radiohead. It’s rumored that Kurt Cobain and Courtney Love dyed their hair in the bathtubs, while Sheryl Crow rollerbladed through the lobby. (Please refrain from doing that now, as it's prohibited.)