Experience Portland One Step at a Time With a Walking Tour
The most comprehensive way to see any city in the Northeast is on foot. Whether you’re learning about the city’s history, or looking to snag a beer in the oldest pub in Portland (which isn’t exactly conducive to driving anyway), walking exposes you to all the elements. The sights, the sounds, the smells (good and bad) waft around the city, giving you a real experience of what life is like here.
We appreciate those who wander and roam without intention. But if you’re motivated by reaching a destination, here are a few spots rooted in Maine’s history that are worth checking out.
Pubs in Historic Maine Buildings
There are two types of folks who fancy a frosty pint; those who earn their drinks after they exercise, and those who need their drinks before they exercise.
It doesn’t matter if this is your first or last stop; pony up to a bar in an historic building. Pubs like 3 Dollar Dewey’s and Gritty’s were established in the 1980s, but the buildings they occupy date back to the mid-1800s. These Old Port staples still have the original bricks and ceiling beams from 200 years of history, which is reason enough to pocket your phone and enjoy a pop or two, admiring an atmosphere rich in history.
Honoring Cape Elizabeth By Way of Hollywood
Portland has many beautiful statues around the city, and one of the highlights is the John Ford statue. Located on the corner of York and Pleasant, the memorial honors one of the first Hollywood directors to be considered an “auteur.” Ford built a prolific legacy in the Western genre, but he also earned a record four Oscars for Best Director in his lifetime, including one for his adaptation of John Steinbeck’s classic novel, The Grapes of Wrath.
There was once a bar named after Ford called “Bull Feeney’s” at 375 Fore St. The name combined Ford’s real last name (“Feeney”) with the nickname he was given during his tenure on the Portland High School football team (“Bull”). Unfortunately, it's gone now; the building is still looking for an owner as of this publication.
Walking as a Work of Art
Another crucial stop is up the hill on Exchange Street, where the Press Hotel resides. The walls display beautiful relics from the building’s history as the former home of the Portland Press Herald. Vintage typewriters and news copy from days of old hang everywhere to commemorate one of the country’s oldest and most respected professions.
The lobby also showcases work from dozens of artists around the state. Like the city itself, the charm blooms from its diversity of mediums, including metal work by John Nelson, pottery by Edgecomb Potters, and prints and paintings by Mainers inspired by their home state. And if you need a pit stop, grab a seat at the hotel’s UNION restaurant. The classy yet accessible dining area is surrounded by large glass windows, giving you a full view of the active Portland streets. Enjoy breakfast, brunch, lunch, dinner, or even small plates and a cocktail.
Follow The Line To Freedom
It’s easy to take Portland for granted as a hub for innovative, modern-day culture. But it’s worth recognizing the city’s long-ago efforts to establish a safe space for enslaved people fleeing the oppressive, early- to mid-19th century South.
The Maine Historical Society worked tirelessly to establish the Portland Freedom Trail, honoring the tens of thousands of enslaved people who fled along the Underground Railroad to find freedom in the United States. The trail honors crucial landmarks with plaques of historical context, including the Franklin Street Wharf, the Barbershop of Jacob C. Dickson, and the Abyssinian Church. The 13 landmarks are mostly set in the Old Port, making it a pretty accessible tour on its own.
It’s important to remember that, like other cities above the Mason-Dixon line, the formerly enslaved still felt the indelible sting of racism when they reached Portland. But this journey is a reminder that every step forward is progress, even if you’re wearing flip-flops.
Parking and Starting Points
Unless you need specific accommodations, you can really park anywhere. But we recommend finding a spot in the Old Port. It’s where most of the action is, and also gives you a home base to allow you to dictate how far you want to journey.
Street parking is plentiful, but depending on the time of day, other travelers could be targeting the same spots. When in doubt, the Casco Bay Parking Garage and the Old Port Square Garage are usually safe bets. But hey…this is a piece about walking. If you have to park far away, that’s more steps to add to the calorie counter!