Transformative American Road Trips: Stories from Coast to Coast

In celebration of the summer Travel edition focused on the enduring tradition of driving across America, we gathered reflections from 13 creative individuals who shared their most impactful road trips. They recounted the destinations, unexpected detours, companions, and encounters that made these journeys unforgettable. Despite their diverse routes, each traveler agreed on one truth: few vacations ignite the imagination quite like a long, winding drive.

Philadelphia to Nashville, 2013

During the early, uncertain days of our relationship, my husband Peter and I spontaneously drove from Philadelphia to Nashville after a hectic Sunday shift at a Mexican fusion restaurant. Fueled by youth and a mixtape featuring country songs from the 1950s to the 2000s, including Kenny Rogers' “Ruby, Don’t Take Your Love to Town,” which later inspired a song on my album, we embraced the adventure. We posed by the Nashville sign, enjoyed traditional Southern 'meat and threes,' and experienced our first honky-tonk at Robert’s Western World. Witnessing a musician's upright bass tricks broadened my understanding of country music’s vibrancy. Though the accommodations were far from luxurious, and I ended up with a severe allergic reaction en route home, the memories from that trip linger in the background of many songs I've written about Peter.

Austin to New York City, 2021

After finishing filming in Austin, I intended to return to New York but found myself lingering in Texas with my newly adopted pit bull, Neon, and friend Ben Levine. We made a sweet stop at ThoroughBread bakery to savor their warm peanut butter and jelly cookie and unique kolaches. At Waco’s Magnolia complex, the crowds were massive, and I tried their renowned chicken salad croissant, delightfully flaky and delicious. Dallas offered expansive, empty streets under the intense June heat, and at one point, the highway shimmered in the distance like a mirage. We dined at a stylish sushi spot with jalapeño-ranch aioli drizzled over a rainbow roll, where I stood out in casual attire amid more formal diners. The trip was filled with meaningful conversations and laughter that helped calm my nerves about the future. Ben also taught me how to properly inflate tires after I faked knowing how—a true road trip lesson.

New York to California, 1973

In 1972, having recently learned to drive at age 24, I journeyed from New York to Arizona photographing with 35mm film. The following year, I embarked on a more ambitious trip using a large-format 4x5 camera, traveling along the old U.S. highway system that passed through the heart of towns. Dressed in a safari jacket and khakis to fit the explorer’s role, I photographed daily, preserving my film with ice packs renewed at motels. I also distributed 56,000 postcards of my images around the country, hoping to connect with audiences beyond New York’s art scene. Unlike earlier experiences where locals were suspicious of my photography, the large camera and tripod drew less concern. One memorable encounter occurred in Ashland, Wisconsin, where a local lawyer, acquainted with my friend John Szarkowski from MoMA, invited me to dinner and a viewing of the Watergate hearings—an unexpected connection on the road.

Santa Barbara to Carmel-by-the-Sea, California, 2024

Touring the Pacific Coast Highway again, a route that has called me back since I was 22 and homeless, I reflected on how music sustained me through hardship. Traveling with my crew in a minivan, we started in Santa Barbara and stopped at a cliffside motel near Pismo Beach. After two shows in San Francisco, I rented a convertible to visit fans and friends at their farm in Sebastopol. My final performance was in Big Sur, beneath towering redwoods at the Henry Miller Memorial Library, where I debuted my song “Endless Tree.” The natural acoustics were breathtaking. We ended the trip at the Carmel Mission Inn, where a morning hike introduced me to the vibrant California poppy—small moments that brought deep joy.

Boston to Coastal Maine, 2022

Following the end of the Covid lockdown, my family embarked on a spontaneous two-month road trip starting in Boston. We drove a rented red Jeep, taking each day as it came. One poignant moment came looking out from a farmhouse in Ghent, New York, where the lush landscape moved me to tears—I hadn’t realized how much I needed that peace. We explored lively Providence, indulged in sardines and ricotta toast, and ventured into Maine’s Bar Harbor, where friends took us on a foggy boat ride to Little Cranberry Island, a community rich with lobstermen. The absence of billboards made the trip feel like a retreat into nature. We spent countless mornings by the water, with my husband and children swimming while I sketched. The journey reminded me to slow down and savor life’s simple pleasures.

Atlanta to New York City, 2013

Shortly after college, my friend Sakinah and I joined mentors Wintter and Mia on their drive from Atlanta to New York for the Afropunk Festival. Packed into a Ford Explorer bursting with luggage, we rode along without knowing how to drive ourselves. The soundtrack was Kendrick Lamar’s “Good Kid, M.A.A.D. City,” and I spent hours gazing out the window, daydreaming as I had as a child traveling from the Jamaican countryside to Kingston. This trip offered me a new perspective on the U.S., from visiting diners and gas stations in North Carolina to exploring monuments in Washington, D.C., whose weighty symbolism left a deep impression. Arriving in New York, I immersed myself in the city’s vibrant creative scene, connecting with diverse communities—a transformative experience that motivated my move there the following year.

Nashville to Memphis, 2017

My bandmate and partner Julien Baker invited me to visit her hometown. She picked me up in Nashville, where I was recording, and drove us back to Memphis, crafting a playlist featuring Memphis artists like Big Star and Three 6 Mafia. Julien is an unpredictable driver, so I focused intently on the road while she sang and danced. The landscape along I-40 features striking rock formations that cascade with waterfalls in the rain. Julien showed me her high school, former workplaces, and the skate park where her band performed. We also visited her father, a prosthetics maker. Despite Julien’s veganism then, we dined at Central BBQ, a Memphis staple she insisted was essential. At Overton Park, I wrote much of my song “Kissing Lessons,” inspired by our deep conversations about our pasts and queer experiences. Road trips offer a meditative space where creativity flows as the horizon stretches endlessly ahead.

Dallas to Tucson, Arizona, 2018

Promoting the Estela cookbook took me to unexpected places. With my friend Sebastian, I drove from Dallas to Tucson, sharing some of the most meaningful conversations about relationships and personal growth of my life. We listened to Fleetwood Mac, Tom Petty, and Neil Young, matching the mood perfectly. Along the way, we stopped regularly to enjoy exceptional barbecue. Tucson’s desert landscape captivated me, especially the saguaro cactuses standing tall outside homes—something I had only seen in photographs before. Visiting Saguaro National Park revealed their impressive scale, water-gathering abilities, and delicate flowers. Though we couldn’t stay for the fiery sunset sky, the cactuses left an indelible mark on me, a spiritual connection I revisit often.

Sioux Falls to Eagle Butte, South Dakota, 2023

While touring a show in Sioux Falls, I detoured to Pierre to bury my father, a parole officer whose jurisdiction included five reservations. As an adopted Lakota, I felt connected to this journey, traveling through Crow Creek, Lower Brule, and Cheyenne River reservations on rural roads. I enjoyed stopping at local lunch spots like V.F.W. halls and American Legions, where meals were hearty and affordable. At a rest stop along the Missouri River, I visited a museum honoring both Lewis and Clark and the Lakota people, paying respects to a large statue of a native woman wrapped in a star quilt. The vast prairie landscape, with its sweeping valleys and tributaries, offered a profound sense of solitude and connection—alone, yet deeply accompanied by memory and nature’s magic.

Chicago to Ithaca, New York, 1992

After graduating high school, I traveled from Chicago to Cornell University to study architecture. This trip marked a milestone for my family, symbolizing a transition from collective experiences to individual paths. My dad rented a dark blue minivan, and we packed sandwiches from the store into a new cooler. With a Rand McNally map marked in red pen, my brother and I curated the road trip playlist, balancing our love of hip-hop with my mother’s dislike of explicit language. Stops included a friendly Wendy’s in Erie, Pennsylvania, where the welcoming atmosphere contrasted with my parents’ memories of travel dangers for Black people in earlier decades. An accidental missed turn led to a chance meeting with a friend also on her way to college, a moment that added warmth to the journey. My mother later admitted to tears after dropping me off, but overall, the trip was filled with joy and hope.

Albuquerque to San Cristobal, New Mexico, 2019

Invited by the Lannan Foundation in Santa Fe to moderate a discussion with scholar and activist Ruth Wilson Gilmore, I traveled with my aunt DeeDee Halleck and my 11-year-old son Remy. The trip began with an unexpected arrival of Lee Lew-Lee, a former Black Panther, setting a powerful tone. We stayed near El Rito amidst striking pink box canyons. On a tense hike, Remy calmly navigated us away from a cliff’s edge. Our journey included art pilgrimages—riding horses past Georgia O’Keeffe’s Ghost Ranch, visiting fiber artist Wendy Clarke and her llamas in San Cristobal, and touring the home of sculptor Nancy Holt in Galisteo shortly before its sale. Holt’s work, steeped in cosmology and desert Zen, felt like a guiding presence, and I felt compelled to heed the directions her art implied.

San Francisco to Healdsburg, California, 2023

Chef Chris Kostow invited us to host an event at his Charter Oak restaurant in St. Helena. Landing in San Francisco, I followed my rituals: lunch at Zuni Café and a visit to Swan Oyster Depot’s counter. From there, we headed to Napa Valley. My companion Rita drove through landscapes marked by wildfire damage, yet the resilience of the standing trees was uplifting. The event brought camaraderie as we cooked alongside remarkable chefs. Afterward, we enjoyed classic American fare at Gott’s roadside hamburger and milkshake spot, despite Rita’s reluctance to eat milkshakes for dinner. Our journey became a leisurely exploration of towns like Healdsburg, Yountville, Sonoma, and Marshall. We admired Schramsberg Vineyards’ cellar treasures and savored barbecued oysters at Nick’s Cove in Tomales Bay. The trip was a rhythm of stopping, eating, sightseeing, and embracing the changing fog and coastal beauty.

These interviews have been edited and condensed.