Maine – Portland: The Old Port and Other Favorites

Now that we have rambled in other parts of the city, we will return to the Old Port with its quaint streets, mid-19th century buildings and layers of Portland history.  Boothby Square, just a block up from the waterfront is bordered on one end by the Customs House.  It is quintessential Portland with cobblestone streets, colorful old buildings (spared by the Great Fire of 1866) and an old stone horse fountain.  The grey building was Samuel Butts home and store and it dates to 1792. 

The other end of the square is anchored by the Portland Regency Hotel, which was built in 1895 as an armory for the Maine National Guard.  After it was decommissioned in the 1950s, it was use as a warehouse until 1984 when developers with a vision of what the city was to become converted it into a luxury hotel. 

Instead of moving further into the Old Port right away, we’ll take you on a little detour one block beyond Franklin Arterial to India Street and into what used to be the Italian neighborhood.   Walk past the horse fountain toward the Customs House and on to Fore Street Restaurant.  Depending on the time of day, you may see the staff stacking the daily supply of wood for their oven fire.  Take the landscaped stairway on your right and you will arrive at the front door of Standard Baking (as good place for coffee and a snack).  Turn left on Commercial Street, cross Franklin and walk one block to India Street with the Grand Trunk Railroad building on the corner.

In Portland’s early days, India Street was the main access leading down to the waterfront and it was lined with homes and businesses.  As the city grew and the congested neighborhood became less desirable, the area became populated by immigrants with India Street becoming a predominantly Italian neighborhood.  The close-knit residents even built St. Peter Parish Church, but for us the most significant reminder of that era is Micucci’s, a flourishing Italian food business that was established 1949 when Emilio (Leo) Micucci opened his food business.  The business is still family owned and run, and it holds fast to its heritage and the tradition of providing the finest products and service for both its retail and wholesale customers. 

This plain-front brick façade gives no hint of the vibrant and delicious offerings inside, from the deli counter with a wide range of cheeses and meats to the aisles of pastas, olive oils, canned tomatoes, capers, etc., to their wine selection and up a short flight of stairs to the spices and cold cases filled with fresh and frozen ingredients as well as separate case of tempting sweets.  If the line isn’t too long, be sure to queue up for a slab of their delicious Sicilian pizza.  That will help sustain you on your walk, but you will probably want to come back later to do the rest of your shopping.  Before you leave, be sure to go out the parking lot door and take a glance at the mural of Casco Bay and tall-masted ships on the wall of the opposite building. 

If you are interested in beer, a tour of Shipyard Brewery (just a block away) may interest you and for English majors, there is a boulder in front of the Marriott Residence Inn that marks the site of Henry Wadsworth Longfellow’s first home. 

For those of you heading back into the Old Port, Middle Street (right outside Micucci’s) will take you into the heart of things.  First you will pass a row of restaurants whose names will be familiar if you have been reading Portland dining and travel magazines: Duck Fat, East Ender, Ribollita, Honey Paw, Hugo’s and Eventide Oyster Co.  A local favorite just a few steps off this stretch is Tomaso’s Canteen, a former workingman’s bar who’s  location and good food has made it a favorite casual meeting place for friends.    

Follow Middle Street past the police station and enjoy the varied architecture that characterizes the Old Port.  At the corner of Exchange Street you will come to Post Office Park, the former site of a beautiful marble post office that was built quickly after the Great Fire out of white marble, a material not suited for northern winters.  It was eventually demolished and the empty lot gave rise to this popular urban park.  The only post box in residence these days is an interesting red post-style that was a gift from Shinagawa, Japan, Portland’s sister city. 

Across the street at Tommy’s Park, Mark Gatti has been selling steamed hotdogs at this location for 37 years now.  In spite of all the fancy food restaurants, his cart is one of the most enduring and endeared food venues in the city (Pierce).  At the back of the park is a new mural that, due to the building’s renovation, recently replaced the trompe l’oeil mural (1985) of the old post office that had stood in the park across the street.    

The new 4-story tall mural was selected from 47 applicants and was completed in 2019.  In the words of the artist Will Sears the design was inspired by “the color found about an hour before sunset incorporating only hues found locally” (Harry).

Standing on the corner between the two parks, you can look up Exchange Street to catch a glimpse of Portland’s City Hall. Across the street, opposite Starbucks, is the Exchange Building.  Originally, this was the site of the Customs House.  The present rich architecturally texture building was built in 1884 as the home of the First National Bank (“Ruins”).

Before turning down Exchange Street, take a few extra steps past Mark’s hotdog cart to visit the “Lobsterman” in front of the Nickelodeon Theater.  We love going to the Nickelodeon on Tuesdays for their $5 movie special.  For now, ignore the snow on the bronze statue, we’ll talk about that later.

This summer Exchange Street got a whole new look when the City blocked the street to vehicle traffic and encouraged the restaurants to create open-air dining venues, allowing them to comply with COVID-19 regulations.  The street is also home to a bevy of boutiques and galleries.  Remember to keep an eye open for interesting architectural details while you are shopping and dining.

Besides window shopping, remember to keep watch for unique trade signs and other interesting architectural and historical details.

If you have a taste for Irish fare or just want to stop for a beer or some other beverage, you might consider Bull Feeny’s on Fore Street.  According to their website the restaurant was named in honor of Hollywood director John Ford (nee John Martin Feeney), who was a Portland high school hero known for lowering “his leather helmet like a bull and charg[ing] through the line.” 

The building itself dates to 1867 and over the years it has had a variety of businesses housed within its walls.  Some time in the early 1940s it “became the Seamen’s Club to attend of the needs of the thousand of sailors in town during World War II.” 

The owners wanted their pub to reflect Portland’s strong Irish heritage so they incorporated a lot of that history into the design.  While you are there be sure to explore both levels to see all the old advertising signs and other pieces they have included in the comfortable décor.  While you are upstairs, remember to pause for a moment to look down toward the harbor through the beautiful arched windows.  John Ford would have approved of this set.

Across Fore Street from Bull Feeney’s are two shops we especially enjoy when looking for authentic Maine gifts.  Skordo offers freshly ground, small batch spice blends and rubs as well as cookbooks and beautiful items for the kitchen and the table.  Their four-jar spice packs are beautifully packaged and always a welcome gift.

Next door Maine Potters Market offers fine handmade pottery pieces from local potters.  They handle a wide variety of styles and price ranges, making it easy to find the perfect gift or souvenir to bring home as a reminder of your stay in Portland.

Fore Street’s curving path follows Portland’s original shoreline and was the main access road to the wharves before the major landfill that began in 1853 to make way for the arriving railroads and create Commercial Street.  The basement walls in many the businesses on Fore Street have waterlines that bear witness to the tides and wakes that slapped against their old reinforced stone seawalls.  The street with its 1850s- and 1870s-era buildings looks much as it did back in the days when huge ships were being loaded and unloaded just a half block below on Wharf Street. 

The cobblestones on Wharf Street slow down your pace but that is fine because it gives you time to take in the unique character of the buildings, shops, and restaurants in this stretch.  It doesn’t take too much imagination to see what this stretch would have looked like, filled with tall-masted ships and sweating, swearing men moving the ship’s cargos.  The dirt and grime are mostly gone, but not the character.  Street and Company, the acclaimed seafood restaurant, is a wonderful choice for a candle-lit dinner in a space that has long been lit by candles and lanterns, and newcomer Central Provisions’ small plates menu is an excellent choice if you are able to score a reservation.  If a beer and a burger are more to your liking, Gritty McDuff’s Brew Pub has been a favorite for locals, as well as tourists, since 1988.   

Many visitors to Portland spend most of their time in the Old Port, which is understandable, but something you might like to consider is a visit to the Victoria Mansion (a few blocks away at 109 Danforth Street).  Built in 1858-1860, the mansion was “the summer home for Ruggles Sylvester Moore and his wife, Olive.  They were both from Maine originally, but Morse made his fortune in New Orleans where he operated luxury hotels” (  Their summer home had all the newest conveniences of the day with “hot and cold running water, flush toilets, central heating, gas lights, a servant call-bell system, wall to wall carpeting, and a 25 foot long stained glass skylight.” 

One of my favorite rooms is the Turkish smoking room with its walls painted like a Bedouin tent.  During a special tour, we were delighted to be able to climb the house’s tower and discover that at the very top, the observatory was also painted in the same tent motif but it was still in unrestored condition.

The month of December is an excellent time to visit the mansion.  A bevy of local florists decorate its lavish interior and turn every room in the home into a holiday tour de force. 

I’m guessing that several readers are questioning my sanity in suggesting a visit to Portland, Maine, in the winter, but it is can be a magical experience.  Yes, it is cold, but nothing that a good down coat, boots and proper layering can’t combat.  The waters of Casco Bay help moderate the temperatures compared with those inland. 

One of the best reasons to come off-season is that the hoards of summer tourists are gone and it is much easier to get reservations at any of the finest restaurants.  Snow gathers on the architectural details of the buildings and the Old Port takes on the look of a scene out of Charles Dickens’ Christmas Carol.  

Bringing in a contemporary perspective to the city streets, local luminary artist Pandora LaCasse’s creations festoon building fronts and parks from the waterfront all the way up to Longfellow Square.  I’m actually eager to pull on my coat, boots, muffler and all that goes with it to walk out into the night and view these bold-colored, geometric designs.  The experience is especially magical when a light snow is falling.  Remember that there are an inviting number of restaurants and pubs that make excellent warming spots along the way. 

The snow doesn’t stop the lobstermen who come down to the harbor to warm their boats in the pre-dawn hours and shovel the snow off their decks into the icy channel before they take off for a day of fishing. 

Hearty joggers and walkers still take their daily walks along the shore and the stark contrast between the dark snow-lined tree limbs and the white snow is stunning. 

On certain mornings when a light wind blows very cold air into a warmer layer of air above the water, Sea Smoke, really a kind of fog, rises over the harbor, creating a magical cloudy effect.    

No matter what time of the year you come, Portland is a beautiful city with a vast array of opportunities to explore. We hope to see you on the streets some time soon.

Recommended Resource:

Harry, David.  “Portland historic preservation panel endorses Tommy’s Park mural.”  December 10, 2018.

Pierce, Kathleen.  “How a 34-year-old hot dog cart has survived Portland’s fancy food explosion.”  June 13, 2017.  Bangor Daily News .com.

“Ruins of the Merchant Exchange.”  Maine Historical Society)

4 thoughts on “Maine – Portland: The Old Port and Other Favorites

  1. Good morning Toni! And of course Don! Another delightful blog in which I learn all sorts of info that I know I won’t retain! Oh dear! Rather a surprise to see myself with you, Toni, in one of your pictures! My daughter Leticia is here visiting (a benefit for me of Covid as her avocado food fairs have been shut down so she visits) and she asked me to say ‘hi’ to you both. Oh when will this all end and movies start again?! I worry that maybe not for a long time, if ever. Keep well! Alice

    Sent from my iPad


    Liked by 1 person

  2. p.s. When are you leaving? After the election? I voted in person absentee two weeks ago in case there were long lines and outside in iffy weather. Go Trump!!

    Sent from my iPad


    Liked by 1 person

  3. Another great tour with areas that we have been to, but obviously missed so much! Can hardly wait to go back and see what we missed!


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