Often I think of the beautiful town
That is seated by the sea;
Often in thought go up and down
The pleasant streets of that dear old town,
And my youth comes back to me.
— on Portland, from “My Lost Youth,” Henry Wadsworth Longfellow
There’s a certain feeling to Portland that’s difficult to name but easy to recognize. Perhaps it’s the way the light moves across the water, or how the streets seem to hold onto their stories. As part of Literary Month at The Longfellow, we’re taking a closer look at the city’s roots, and tracing a path through Portland where its literary history still quietly lingers.
Visiting the City’s Storied Past
Longfellow Square. At the center of the city, Longfellow Square offers a natural starting point. Anchored by a statue of Henry Wadsworth Longfellow, the square serves as both a landmark and a reminder of Portland’s deep literary ties. It’s a place to pause, take in the surroundings, and consider the legacy of a writer whose words continue to shape the identity of the city.
Wadsworth-Longfellow House. Just a short walk away, the Wadsworth-Longfellow House offers a more intimate connection. Preserved by the Maine Historical Society, it’s the childhood home of Longfellow and one of the oldest standing structures in Portland. Inside, rooms are carefully kept, offering a glimpse into early life in the city and the beginnings of a literary voice that would resonate far beyond it.
For those interested in going deeper, the Maine Historical Society provides a broader look at the region’s past, connecting literature with the people and events that shaped it.
Longfellow’s Birthplace Marker. Along Fore Street, near the Residence Inn, a simple stone marker notes the site of Longfellow’s birthplace. It’s easy to miss, but worth seeking out. There’s something quietly meaningful about standing in a place so unassuming, knowing it marks the beginning of a life that would leave such a lasting imprint on American literature.
A City Best Explored on Foot
Portland’s literary history is best experienced at a walking pace. Along the way, you’ll notice the small details, historic facades, shifting views of the harbor, that bring the past into focus.
For a more guided experience, Maine Day Ventures offers a thoughtfully paced walking tour through the city’s past. Beginning in the Old Port and moving through downtown and the waterfront, the experience traces more than 300 years of history, from maritime industry and architecture to the lives of poets, artists, and changemakers who shaped the city. It’s an engaging way to see Portland through a wider lens, with stories that connect its literary roots to the broader sweep of Maine’s history.
A Broader Literary Legacy
And let’s not forget, Maine’s literary roots extend well beyond Portland. The state has long inspired writers drawn to its landscapes, its seasons, and its distinct sense of place. From the poetry of Edna St. Vincent Millay in nearby Rockland to Harriet Beecher Stowe, who wrote Uncle Tom’s Cabin while living in Brunswick, Maine has shaped voices that continue to resonate far beyond its borders. That tradition carries forward today in the work of contemporary authors like Stephen King, Lily King, and Elizabeth Strout, each offering their own perspective on life across the state. There’s a shared thread of observation and atmosphere that runs through their work, a tradition that continues to evolve, shaped as much by the present moment as by the past.
Celebrate Literary Month with Us
Portland invites you to explore at your own pace, to follow its stories as they unfold from one street to the next. And when you’re ready to continue the experience, we’ve gathered a selection of our favorite local bookshops in a companion guide on our blog, offering even more places to discover and settle in with a good book.
Interested in connecting with the Maine literary community? Join us on April 16th for Sips & Stories – an event that pairs two of life’s greatest pleasures: good books and great drinks.
As Literary Month continues at The Longfellow, we look forward to sharing more of what makes this city such a meaningful place to read, reflect, and stay awhile.