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Author of The Great American Retro Road Trip: A Celebration of Roadside Americana – and executive producer for digital content, innovation, and strategy at WABC-TV Channel 7 – Rolando Pujol first received praise for a book he had written when he was in grade school. “In formal and informal capacities, I’ve been a writer my entire life,” he explains.

During his time at a parochial school in North Tarrytown (now Sleepy Hollow), NY, Rolando wrote and published a short story, two books on religion, and one book on astronomy. He recounts these early memories of writing as not only elucidating his passion for the written word, but also giving him first-hand experience with the realities of the craft.

“I’m being exceedingly generous when I say they were ‘books’ that were ‘published,’” Rolando jokes. To show his encouragement and that he was impressed by his work, Rolando’s father typed up his son’s efforts, and the two worked together to bind them into small books with cardboard paper, staples, and tape. “One of my elementary school teachers read the first three to the class and affirmed my humble efforts,” muses Rolando.

However, the next year, Rolando received what he refers to as an early example of rejection. When Rolando presented a different teacher with his final childhood book, she dismissed it, tossing it in her desk’s junk drawer. As time went on, it was clear she had forgotten about it. Rolando asked for the book back at the end of the school year, only to have the copy returned to him scuffed and ink-ridden.

While that incident stuck in Rolando’s memory, he clarifies, “That early encouragement from my dad and a kindly nun was enough to propel me forward, and the indifference shown by the other teacher was a lesson, too, that not everyone is going to appreciate what you do.”

A journey through journalism

Like many writers in their formative years, Rolando explains, he spent his time “looking for any excuse to write.” He points out how in his teens, from showcasing his writings in the church’s Sunday bulletins to writing and editing for his high school paper, he encountered plenty of opportunities to do so. 

Once he went to college, he wrote and edited for Columbia University’s Daily Spectator while majoring in history. He owes much of his academic inspiration to history professors Alan Brinkley, Eric Foner, and James Shenton. He also notes journalism idols Charles Kuralt, Charles Osgood, Jack Perkins, and Bob Dotson, who clarified the type of journalism Rolando was eager to pursue. 

“It should come as no surprise that my work has primarily centered around Americana-based storytelling, tales from the road, interesting people and places, and pockets of storytelling where history meets journalism,” he states. “The two fields are one and the same, with journalism the first and most crucial step in the documentation of history.”

While still in college, Rolando took his first job as a newsroom assistant at The New York Times, a role that he credits as not only making a significant impression on him, but also focusing his attention on print, despite the emerging digital scene circa 1995. “I never really considered any other career path: journalism, in some form, it would be,” says Rolando.

Counting himself fortunate to have worked for the Long Island and New York editions of Newsday, as well as The New York Daily News, Rolando also worked locally as a news editor at what is now The Journal News in White Plains, NY. He observes, “Soon, I found my subjects of interest weren’t just limited to news, and I began to write about history, preservation, arts, and culture.”

Indeed, while serving as managing editor at amNewYork, Rolando began writing about these new topics, and also launched several blogs. From there, he went on to work at a number of television stations, including WNBC-TV – where he contributed a regular on-air segment, Hidden City, featuring content reminiscent of that in his new book – and WPIX-TV. Now, he works as the executive producer for digital content, innovation, and strategy at WABC-TV Channel 7. 

Formative, familiar inspirations

Just as writing and journalism impacted Rolando’s youth, so did his upbringing in Sleepy Hollow. Growing up in the setting of Washington Irving’s The Legend of Sleepy Hollow left a resonant impression on Rolando; he remembers learning everything he could about Irving as a child. “Growing up in Sleepy Hollow, NY, was a seminal experience because the region is suffused with history and lore. You live among the ghosts,” he asserts.

As a child of Cuban immigrants, Rolando also notes how this impacted his family’s relationship with the country around them. “Growing up in a family of immigrants instilled in me both a special pride and a perpetual sense of otherness, and endless questions about my ‘Americanness,’” Rolando describes.

This tension is encapsulated in a 1977 incident where Rolando’s father had the door slammed in his face when trying to introduce himself to a neighbor. However, Rolando clarifies, this ignorance was not the complete picture of his experiences growing up, and much of the good is owed to the types of places featured in his book.

“Many people were deeply welcoming and gave me trust in and admiration for our American system and instilled in me a desire to be a productive part of it,” recalls Rolando. “I saw roadside Americana – the Howard Johnson’s, the McDonald’s with their McDonaldland PlayPlaces, the old candy shops – as a vivid and beautiful manifestation of America, and we were always welcomed in those places.”

Rolando only grew to love and appreciate these spots even more as he got older. “These places were a symbol of an America I could be a part of,” he points out. “There’s a reason the subtitle of the book is A Celebration of Roadside Americana. There’s a lot to celebrate about these places, and they often don’t get their due.”

Launching “The Retrologist”

With this deep, nostalgic interest blossomed a motivation to capture and share stories about all that is retro and roadside. It wasn’t until the spring of 2012, however, that “The Retrologist” began in earnest, with the launch of Rolando’s Tumblr blog and the start of his Instagram posts.

He decided to dedicate a new space, beyond his Twitter account, to writing, sharing, and building community, specifically related to his interest in vintage or old-fashioned places he’s come across, whether they be active businesses or long-gone remnants of what used to be. Discovering and telling the stories of these places, and sharing them with an audience, is at the core of “The Retrologist,” a neologism he aptly chose to describe his work as “an unofficial expert in studying and celebrating the past, those things ‘retro’ or vintage.”

Rolando adds that what started out as merely a curiosity quickly became a new calling, and skyrocketed thanks to social media; his largest following is on Instagram where he has over 94,000 followers. “When I doubled down on Instagram as a creative outlet in 2019, the account took off, and it soared during the pandemic, when my photos and musings from my travels resonated with readers trapped at home, restless and full of wanderlust,” Rolando recalls. 

What exactly does Rolando mean when he refers to “roadside Americana,” you might ask? Whether it’s “quirky roadside attractions like giant buildings shaped after the product they sell or represent: giant coffee pots, ducks, shoes,” or “iconic pit stops like South of the Border, off I-95, with a kitschy theme and billboards along the way to build excitement and anticipation,” these spots and landmarks can consist of just about anything vintage or nostalgic that’s meant to grab your attention and make you stop by.

Curious mom-and-pop stops or “world’s biggest” creations also fit the bill. Rolando notes that their being roadside relates in large part to the development of these places parallel to the car and national highway system. “But,” he notes, “they can just as well be on Main Streets, with homey barber shops and cute ice cream parlors that add charm to American downtowns.”

The looming potential for a book

Rolando explains that from the very beginning, he was always encouraged to write a book about this work, to the point where he began to worry about his capability, or if the concept was even viable. In his eyes, Instagram posting and book writing were on two different planes.

Rolando recognizes that this angst persisted despite the support of many people, from an old boss to an old newspaper colleague. This colleague not only offered constant support on Facebook, but in his last exchange with Rolando after the colleague became terminally ill, he once again encouraged him to write a book. Rolando acknowledges him by name in The Great American Retro Road Trip, and was deeply touched by this final interaction with him. “Truly, I did not lack encouragement,” Rolando observes.

In 2022, Rolando launched his Substack. Also around this time, he began considering a book pitch for publishers. Then, he says, “the moment of kismet happened.”

An email from an Artisan Books (Hachette Book Group imprint) editor inquiring about Rolando’s interest in writing a book landed in his inbox. Shortly after, Rolando signed a contract to write The Great American Retro Road Trip and recognized just how much his past efforts had culminated in this fulfillment of a childhood dream. “I soon realized I had been writing this book my whole life,” he explains. “Now, I had a deadline.”

Where to next?

Rolando describes his research for “The Retrologist” and his book as “endless and constant.” Having built digital maps for every state, as well as many countries, Rolando plots places he wants to visit and creates ever-growing lists that draw upon a variety of sources: websites, articles, social media posts, Google Street View, tips from readers and commenters, or random strikes of inspiration, like a place spotted in the background of a TV news report. 

While he likes to keep a basic itinerary when going on a trip, Rolando also lets recommendations or discoveries along the way change his plans. On a 2022 Montana trip, he explains, “I ended up blowing up my plans after multiple people suggested I visit the Sip ‘n Dip in Great Falls. The tiki-style bar, since 1962, features ‘mermaids’ swimming behind the bar. I HAD to see this, and the location made the cut in my book, of course.”

With such a wealth of places he’s explored, Rolando found that in addition to balancing travel and writing for his book with a demanding, news cycle-reliant career, it was challenging choosing which locations to feature. The Great American Retro Road Trip encompasses every contiguous state (the lower 48; he hopes to include Alaska and Hawaii in the next book).

You’ll not only find plenty of roadside attractions, like the Flanders, NY, Big Duck or the Newark, OH, office building shaped like a massive Longaberger Basket, but you’ll also stumble upon a variety of quirky gems like a parade of dinosaurs, fiberglass Muffler Men, and the world’s smallest Buc-ee’s, situated deep in the Texan desert. This is, of course, in addition to a slew of ice cream shops, drive-ins, diners, and more. 

“Among those nearest to my heart,” reflects Rolando, “is South of the Border in Dillon, SC, which I first visited as a four-year-old during my first trip with my family, and Wall Drug in Wall, SD, which was a stop on my first solo cross-country road trip when I was 25.”

The significance of preserving roadside Americana

The Great American Retro Road Trip is not just about the places themselves, but understanding what it means to appreciate the built environment on a deeper level (using what Rolando calls “Retrologist Spectacles”). He seeks to encourage a sense of joy, fascination, and wonder in everyday life: “You can find curiosities and hidden stories in the most pedestrian strip mall.”

In bringing about this sense of optimism and curiosity, Rolando also hopes “to help us all understand how much we have in common,” which he recognizes is crucial now more than ever.

Part and parcel of this aim is supporting the small shops and businesses featured in the book. Rolando hopes to celebrate and preserve their characteristics and stories amidst an increasing homogenization in the country’s retail landscape that’s only been worsened by online shopping. He also wants to ensure that these spots will stay open for years to come.

“Buying the book and finding out about these places is a wonderful way to then get out there and support these shops. I want these places to survive for the enjoyment and enrichment of people not even born yet,” Rolando states. “This is exactly what is at stake: historic institutions that give our communities character, that add layers of richness that cannot be replaced when they are gone.”

To learn more about Rolando and explore “The Retrologist,” please visit his Substack rolandopujol.substack.com and follow him on Instagram @rolandopujol. To order your copy of The Great American Retro Road Trip: A Celebration of Roadside Americana, which was released on June 24, 2025, please visit hachettebookgroup.com/titles/rolando-pujol/the-great-american-retro-road-trip/9781648293719/.