You Can Get There From Here:  A Mainiac’s Peek at Portland

By Ava Kabouchny

“Beautiful sunrise, isn’t it?”  “Good morning.”  Or just a friendly “Hi.”  This is how Portland, Maine, wakes up.  Having just returned from living in France for almost five years, I began to wonder if there is something in the ocean air, or water in Portland that makes everyone so friendly. 

That is not to say that the French reputation for lack of friendliness is correct, but the mornings just feel different here.

Getting to Know Portland:  Discovering Portland’s Secrets

So, wanting to know about this small, well-reputed New England city surrounded by water on four sides and having a population of only 68,000, I got onto a tour bus where the guide was my longtime friend and travel buddy, Charlie Frair.

Charlie has been guiding tourists from the small cruise ships that travel from Portland to Bar Harbor with stops in some of Maine’s other coastal cities along the way. 

Charlie’s sense of humor and gift for storytelling has served him well since he decided to become a Portland tour guide, doing so with great enthusiasm for about five years now for the Maine Tour Connection.

Mainers vs. Maniacs

With forty-eight passengers from all parts of the U.S. wanting to get a taste of Maine, I boarded Charlie’s bus where he told us about his Colorado roots.

But that he is now a transplanted Mainiac – the name given to us Maine residents who are ‘from away.’  That means those of us not born in the least populated state east of the Mississippi and crazy enough to stay in Maine after a first winter.  Those with the distinction of having been born here are simply called “Mainers.”

Hidden History of Portland:  Speaking Easy

The first bit of Portland history told by Charlie was about the city’s ‘father of prohibition’ Neal Dow, whose laws resulted in the Maine Law, making Maine a dry state from 1851 to 1933 when national prohibition was repealed.  During Neal Dow’s tenure, no alcohol was allowed to be manufactured, traded, or consumed, so speakeasies took hold, underground bars where homemade beer or other libations could be found. 

One speakeasy still exists, unknown even to most Mainers (or Mainiacs), but Charlie pointed to the street where it is located.  The entrance is so nondescript that no one would know of the staircase that leads down to a place where a bookcase hides the entrance, and only a few even savvier people know how to manipulate the bookcase to make it slide and reveal the door.  

(The evening of the tour, Charlie took me to this hidden speakeasy, where we enjoyed a glass of beer for five dollars, the cost of any drink, which must be paid for in cash.  Not even I, a Mainiac, will reveal its location only to say it is near Market Street.) 

Interesting Portland fact – the Maine Women’s Christian Temperance Union is now headquartered at 714 Congress Street in Portland, the house being the original home of Neal Dow and his bride.

A City Rebuilt from the Ashes

Most of Portland’s downtown area, once made mostly of wood, was reconstructed in 1866 when a total rebuilding was necessary after either a firecracker or a cigar started a fire in a boathouse on July 4, 1866, destroying 1800 buildings of which 1200 were residences while the rest were government buildings, churches, hotels, and shops. 

Portland’s Great Fire eventually put itself out on Munjoy Hill in the city’s east end.  Over the next wo years, the downtown area, where many of the tourist sites and a plethora of lobster and seafood restaurants are now located, was rebuilt in traditional New England red brick, a style in which the architects took great pride.  The downtown area has remained largely unchanged since its reconstruction.

A Home to Henry Wadsworth Longfellow

At 489 Congress Street, visitors are welcomed into the distinctive four-chimneyed boyhood home of American poet and writer, Henry Wadsworth Longfellow. 

Now a National Historic Landmark, the Wadsworth-Longfellow House is the oldest building in Portland and the first named historic site in Maine. 

Paul Revere’s Ride (1860), written by Longfellow eighty-five years after the famous ride, and The Song of Hiawatha (1856) are perhaps his most famous poems.  Longfellow also wrote about New England’s unpredictable weather, which greatly affected his moods.  Here is one small sample about his love of spring:

If Spring came but once a century instead of once a year, or burst forth with the sound of an earthquake, and not in silence. What wonder and expectation there would be in al; hearts to behold this miraculous change.  (Seasons)

Portland’s Most Famous Lighthouse

Henry Wadsworth Longfellow would often walk to Portland Head Light, thought to be Maine’s most photographed lighthouse, from his home on Congress Street and that walk, he claimed, influenced his poetry and writing. 

Bruce Garrow, a city park employee, and friendly greeter near the lighthouse, offers a bowl of cold water for visitors’ pets and a suggestion of where the best view of the lighthouse is  Not only the walk to the lighthouse but put onto America’s list of National Monuments in 1973. but also the lighthouse itself surely must have influenced Longfellow’s writing.  Seeing it is quintessential Maine, a view not to be missed.

A Hollywood Connection

Jumping to the 1950s and to the well-known actress of that time, Bette Davis, who while married to actor Gary Merrill, lived with him for ten years in nearby Port Elizabeth.  Together they used their wealth to invest in art and music and helped give Portland its name as an art and music center. 

Merrill Auditorium is named for its benefactors and is a center for concerts, plays, operas, high school, university, and law school graduations, and the inimitable performances of Maine comedian, Bob Marley, not to be confused with another, definitely more famous Bob Marley.  The Maine Bob Marley may have coined the phrase “You can’t get there from here,” the answer from a true Mainer to a lost tourist trying to get to Harrison. 

“Hmmm.  Hmmm,” the Mainer says, “Now let me think a moment.  Harrison, Harrison.  Ya can’t get there from here”, said Bob Marley’s authentic Mainer accent.

A Center of Arts and Culture

Portland’s growing reputation for the arts has made the Portland Museum of Art a well-visited spot for both locals and tourists.  The PMA has a large collection of American, European, and contemporary art, including works by local Maine artists. 

A gift by philanthropist, John Chipman Payson in 1976 of seventeen paintings of the 19^th century Maine-born landscape and marine artist, Winslow Homer, precipitated the building of the Portland Museum of Art as it stands today, completed in 1983. 

The PMA was founded in 1882 by the Portland Society of Art and in 1908, by Margaret Joane Mussey Sweat. gave her three-story mansion, now known as the MacLennan House, worth a visit to see its free-standing staircase, and sufficient funds to the Society to create an art gallery dedicated to her husband.

Unabashedly Called the World’s Best Lobster

Food, and especially seafood, and especially lobster is not to be missed in Maine’s city by the sea, which has more restaurants per capita than any other U.S. city outside of San Franciso, and Portland’s small size makes them all two hundred and eighty-seven of them easy to reach. 

Even though I’m from away, that is, a Mainiac, I can attest to the sweetness of the meat of a Maine lobster, which in my humble Mainiac opinion, is the best anywhere.  More than 100 million pounds of lobster, 90% of the country’s lobster supply, are harvested in Portland every year and is done so sustainably. 

The lobsters are hand-harvested from small dayboats, and undersized and oversized lobsters are returned to the sea.  If eggs are present on a female lobster, the fisherman notches the lowest part of her tail and returns her to the sea. 

DiMillo’s restaurant, formerly a New York ferryboat, is a touristy Portland landmark and reservations are needed to enjoy the ambiance and the harbor views.  However, walking down just about any of Portland’s side streets, most still looking like they did decades ago, visitors will come upon terraced restaurants serving Maine’s delicacy in many different forms. Commercial Fish Market is where to go if you’re cooking, otherwise there are many great choices on the Portland waterfront. 

If you’re a purist, however, you will order a whole lobster, still in its shell, served with a wedge of lemon, corn on the cob, and a small pot of drawn butter.  Almost heaven. End your meal with a slice of blueberry pie (the blueberry is Maine’s official state fruit) and you’ll almost be a Mainiac, or at least have a sudden desire to become one.

And the Best Brew Pubs

Among Portland’s first immigrants were the Irish, and until COVID-19, anyone with the last name O’Brien could go to the Brian Boru Public House on Center Street and have a free beer. 

Alas, the public house never reopened after the pandemic, but a simple Google search of Portland Maine Beer will reveal the names of 20 brew pubs, most located on the waterfront. 

One of those pubs with a restaurant and free popcorn is Deweys, also once known as Three-Dollar Deweys, so-called for a reason not to be explained here. 

Deweys is Portland’s original alehouse and was voted the city’s best craft beer pub with forty-two tap lines. 

Located in the Old Port at the corner of Commercial and Union Streets, it is easy to spot – a pirate looks down from a corner window, and another greets restaurantgoers when they open the door.

Bourbon Street in Portland

On summer Friday nights, the downtown area of Fore Street, replete with numerous bars housed in New England red brick, turns into Portland’s facsimile of Bourbon Street. 

A section of Fore Street is closed to traffic so the revelers can enjoy their choice of drink while standing on the red brick sidewalks and on the street and going from brew pub to brew pub.

A Walk Up The Hill

Portland is a very walkable city and visitors can stroll up Congress Street and visit the Children’s Museum, the Theater of Maine and other theaters.

Also visit the Eastern Cemetery, where people who shaped the city’s economic, cultural, and social development are laid to rest along with soldiers from the colonial and civil wars. 

An estimated 7,000 people are buried in the cemetery’s six acres, which offer a view of the Casco Bay Islands and Portland Harbor.  Further up on Congress Street is the Portland Observatory, where a raised flag historically meant that a ship was ready to unload its cargo, such as molasses. 

A climb up the 105 steps gives a view of Portland’s historic architecture and of the harbor and Casco Bay.  The area at the top of the hill is known as Munjoy Hill, an area where many workers in the 19^th century built their homes, and at the base of which were workers from the West Indies who lived there because of the molasses trade.

Munjoy Hill is a now neighborhood of small specialty restaurants, some of which have outdoor seating in summer.  A right turn towards the ocean from “The Hill,” as it is known locally, leads to the Eastern Promenade with views of beautiful captains’ houses and Fort Allen Park, where a monument of a restored ship’s mast from the USS Portland looks over Casco Bay. 

Cargo ships during the Second World War, known as Liberty Ships, built in South Portland, were in a large part built by Wendy the Welder, Rosie’s little-known cousin.

Many Reasons to Visit Portland

Visiting Portland is a city where visitors will enjoy its friendliness, its art, its cultural and historical offerings, its safety, its working waterfront, and its incomparable, simply cooked, delicious seafood. 

Add all of that to a tour with Charlie Frair as your guide, and he might even take you to the secret speakeasy for a wicked good, five-dollar beer.