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When it comes to cities named Portland, I will admit to a bit of my heart will always be in my hometown — the “other” Portland, way out west in Oregon. But I can also say that Portland, Maine, has captured a pretty big piece of my heart, as well.
A two-hour drive south from Bangor, Maine’s largest city is a funky mix of old and new, whether you are talking about architecture, food, drink, museums, galleries, shops or markets. It’s an urban area that’s also a hop, skip, jump or bicycle ride from some of the state’s best natural sea and land resources. In other words, it’s perfect for a day trip, weekend getaway or leisurely multi-day vacations. And I’ve done all three.
So, let’s break it down!
It’s a straight 130-mile shot south down Interstate 95 and on to Interstate 295 from Bangor into Portland. You can also take an alternate route by staying on I-95. Either way, it’s about two hours, and you are looking at a minimum $1 in road tolls, regardless which of the two routes you select. Frankly, I kind of enjoy the 10 or seconds it takes to hand over my toll money and exchange a pleasantry or two with the toll booth operators.
Whether your plans are just for a day trip or to spend a more extended stay in Portland, I recommend finding a convenient spot to park, lock your car and head out on foot. Traffic in the city can be heavy during working hours and parking a bit tricky to find. There are a number of parking garages downtown in addition to metered street-side parking, which is free on Sundays. When I drive into Portland, I start looking for the first available spot when I am still several blocks from my destination. Once I spot one, I pull in. Quite frankly, Portland is a city made for exploration on foot.
Ready to head out?
Among the more popular attractions in Portland — and for good reason — is the Old Port.
Running along Casco Bay and bordered by Commercial, Middle, Union and Franklin streets, Portland’s Old Port is five blocks of working waterfront, unique shops, historical buildings and enough photo-ops to fill a memory card and then some.
You can’t help but get a sense of the city’s past when you’re walking on the Old Port’s cobblestone streets. What is now Portland was first occupied by Europeans in 1632. When Maine became a state in 1820, Portland was the state capital for 12 years before it was relocated to Augusta.
These days the Old Port — much of which is on the National Register of Historic Places — is the heart of modern Portland and provides a window into its past. Many of the businesses in the Old Port are housed in 19th-century warehouses and buildings that were saved from demolition in the 1970s, thanks to forward-thinking historical preservationists.
One of my favorite things to do in the Old Port is to grab a coffee to-go and find a bench to sit on overlooking the harbor and Casco Bay. If I look hard enough and let my mind go free to imagine, I can look through the forest of modern sailing ship masts on boats bobbing at their moorings and can almost see those fishing boats or merchant schooners from another age centuries ago sailing or steaming into port. This vision is helped by the sounds and smells of this working waterfront — seagulls screeching overhead, fog horns sounding, sea air blowing and the hustle and bustle that comes with a working waterfront, regardless of era.
Back in the present, my feet often take me over the cobblestones, and I am happy to spend an hour or two window shopping and ducking into shops that catch my fancy. And trust me, with dozens of unique, locally owned shops in the Old Port, my fancy is caught a lot. Whether you are in the market for locally sourced seafood, hand-made candy, craft beer, custom jewelry, Maine-inspired fashions, books by local authors or even something for your pet, you are going to find it in the Old Port.
When it comes to the arts — be it visual, musical or any other medium you care to mention — Portland has you covered. The Portland Arts’ District is a short walk from the Old Port up to Commercial street where you are going to find museums, galleries, performance venues and several great restaurants.
The Portland Museum of Art has quite the collection of permanent exhibits showcasing American, European and Maine artists. In March be sure to check out the exhibit “Relational Undercurrents: Contemporary Art of the Caribbean Archipelago,” featuring works depicting the impact of the area’s colonial past on its contemporary art and culture.
Never let it be said that the Portland art scene takes itself too seriously. The three-day homage to all things Felis catus, also known as CatVideoFest, will be held at the Portland Museum of Art on March 29 to 30. The event raises funds for cat shelters and cat charities with showings of cat animated videos, cat music videos and internet cat vignettes.
At the Children’s Museum and Theatre of Maine you only have to be young at heart to enjoy all the exhibits geared toward imagination and learning. Kids can discover their own superpowers at the museum’s Action! Headquarters! Exhibit where they can try out a secret identity, choose a superpower and act out their heroic Portland-themed adventures on an actual stage with puppets! Come on, how much fun is this?
When not saving the day, kids can explore the world of light and cameras, learn about Maine’s local food movement or create their own experiments to explore the world of motion. Sure, it’s all for kids, but I dare any adult not to jump in and play along.
For live performances, check out The State Theatre that offers an array of musical and theatrical acts ranging from kid-friendly concerts to modern indie rock bands in the 1,800 seat venue.
Portland Stage Theatre of Maine offers live productions drawing talent from Maine and around New England on its Main Stage. It also showcases experimental theater acts in the smaller, 75-seat theater.
Then there’s the architecture in the Arts’ District where a stroll along Congress Street is another walk into Portland’s past.
There’s the Wadsworth-Longfellow House where poet Henry Wadsworth Longfellow grew up. The house contains original artifacts and household items belonging to the family. Head out back and check out the garden planted on what was the Wadsworth-Longfellow family farm plot.
For something a bit on the quirky side, head over to the First Parish Church and check out the 600-pound chandelier with the cannonball shot during the Revolutionary War in its center. The 16th-century church, which welcomes people from all denominations, is the oldest house of worship in Portland. One of the pews still bears the Longfellow name from the days the family worshipped there.
And for trivia buffs, here are two fun historical Portland facts to experience and share. Portland’s City Hall was built by the firm Carrere & Hastings, the same designers of the New York Public Library. And, Portland High School is believed to be the oldest standing high school in the country.
Head to Portland Head
When you’re ready to step away from the city, it’s a short drive from Portland to Cape Elizabeth and Portland Head Lighthouse at Fort Williams Park. Regardless of the season, it is well worth the trek as the iconic light and red-roofed keeper’s house are postcard picture perfect no matter the weather or time of year.
It was built in 1791 at the entrance to the primary shipping channel leading into Portland Harbor and Casco Bay and is the oldest lighthouse in the state. Today the light and park include 90 acres of hiking trails, a museum and gift shop.
Where to eat
Portland has found itself on the top of numerous foodie and restaurant lists, so it’s really hard to go wrong when looking for something to eat in this city. But I do have some favorites based on personal taste-testing experience.
Pai Men Miyake is a small restaurant with not a huge amount of seating and a limited menu. But it’s well worth the wait for a plate of the pork gyoza — steamed dumplings stuffed with Wolfe’s Neck Farm pork and cabbage. The gyoza simply melt in your mouth. Another favorite is the Katsudon rice bowl with panko-fried pork loin that has a crisp texture and divine flavor of pork that blends with the bowl’s pickled red onions. If it’s too crowded to get a table when you first arrive, simply give your name and contact number to the hostess and pop in next door at LFK for a crafted cocktail or sample one (or two) of Portland’s microbrews while waiting for your table.
I had one of the best burgers ever at The Great Lost Bear. The Bleu Burger is a half-pound of Angus beef covered in a gooey, hot blue cheese sauce. Add bacon, tomato and lettuce, and you have grilled heaven on a bulkie roll. With around 80 local and imported beers on tap, Great Lost Bear was named Maine’s best beer bar last year by Craftbeer.com.
Admittedly, I have a bit of a sweet tooth, and among my favorite Portland places to satisfy it is The Holy Donut. In either location, you will find a nearly overwhelming array of homemade donuts in which Aroostook County potatoes, local berries and fruit, local butter and New England eggs are the key ingredients. My favorite Maine-themed flavors are maple bacon, blueberry, apple and — wait for it — Allen’s Coffee Flavored Brandy.
Where to stay
The Portland Regency Hotel & Spa is perfectly located in The Old Port. Housed in the old armory, the hotel offers valet parking ($20) in a secure lot. There is an onsite restaurant serving traditional New England fare — lobster anyone? The bar at the hotel serves cocktails, beer and pub style food. This hotel is pet-friendly.
Holiday Inn Portland by the Bay is walking distance to everything fun downtown in Portland. This Holiday Inn has onsite parking [$10 a night], which makes it a perfect place to stay if you want to leave the car and explore by foot. It’s also overlooking Casco Bay and some rooms have that waterfront view. While this is not a pet-friendly hotel, it does allow certified service animals.
If not staying in a hotel, I am a huge fan of Airbnb accommodations. A quick search on the Airbnb site turned up 173 houses, apartments or rooms scattered around the city and available for short-term rentals through the site.
This story was originally published in Bangor Metro’s March 2019 issue. To subscribe to the magazine, click here.