How to Fall in Love with Portland, Maine

How to Fall in Love with Portland, Maine

On an early May morning, I stepped off a Greyhound bus and onto a foggy street. A heavy carpet of mist blanketed the city that I had just arrived in as I inhaled the frosty air. This was probably the last spot in America that was still breathing in winter. I had just landed in Portland,Maine.

I walked passed by old Victorian mansions with large naked trees in their front lawns. They were dotted with crocuses around their base and other signs of spring approaching. The forewarnings of winter’s end had been actively happening in the rest of the country for a month already. Portland was a little late to the seasonal trend.

As I walked through the maine ( ugh, I’m sorry) main intersection at Congress and High street, I couldn’t believe that this was the epicenter of the town...I mean city. A few of the red brick buildings were higher than four stories. It seemed that as soon as you walked into the center you walked out of it. It felt like a larger version of a town from the Berkshires, cozy and calm. At a high traffic intersection, the cars still slowed down for pedestrians with no hints of road rage.

There was something effortlessly charming about it. The signs of commercialism hadn’t fully swallowed up the city center by the big box stores ( but there was one Starbucks). Portland, Maine holds all of the quaintness of a town while still being able to claim that it’s a city and has been placed on the list of one of the best small cities to live in the United States. After spending a weekend there, I totally understand why.

The city’s red brick buildings, abundance of trees, and always being able to catch a glimpse of the ocean has somehow maintained some of that old-timey magic that big city folk ache for as they sit in their high-rises, crowded subways and long commutes. Portland is one still a place that reminds visitors of a slow pace, low stakes, tranquil way of living.

The well preserved brick architecture is what got me. Only because preservation has been something that Portland has always been fighting with. The city has gone through no less than five fires in its time. The most destructive one,  the Great Fire, happened in 1866.

Most of the town ( ugh I’m sorry “city”) was burned to the ground due to an Independence Day celebration ( that’s like getting burned alive at your birthday party). It incinerated most of the town: the commercial buildings, churches, and hundreds of homes. But Mainer’s aren’t ones to complain. They know how to tough it through a hard situation ( I mean they willingly live there during WINTER).  

So like a phoenix rising from the ashes, Portland rebuilt itself in brick and Victorian styled homes and architecture. It  is one of the few little cites that is part of the  National Register of Historic Places ( it’s like America’s personal UNESCO). Which is why it feels a little older than other modern American cities.

The more I have traveled in my life, I have wondered why certain spots strike me more than others. It feels more than just the conversations I am having or food I am eating, but why do some places captivate me?

I feel a certain alignment with the place and have slowly figured out why. It is the places that prioritize my similar sense of comforts

I think every traveler, no matter how far away they are, are always looking for pieces of home. Our brains have a funny way of always looking out for what feels familiar. Even travelers, who actively are searching for different, subconsciously always want home.

For me that is four things: bookshops, coffeeshops, nature, and art.

Portland conquered all of them. I couldn’t walk for more than five minutes without running into another coffeeshop, bookshop, or gallery in order to warm up during this brisk spring weekend and the view of the ocean was always within a five minute walk.

I was attending WITS, the Women in Travel Summit, and unfortunately was cooped up in hotel conference rooms most of the time and wasn’t able to explore as much nature as I would have liked.

I only had the weekend, but if you are looking for a cozy weekend somewhere that really does appreciate the good life- great food, connection to nature, and artistic edge- then go no farther ( which you really can’t go farther north if you want to stay in some semblance of civilization) and nestle up in Portland, Maine.

Where To Stay

Tuck in at the Francis

Although I will always be a die-hard backpacker, during the conference, I needed to prioritize my comfort. I wanted to stay someplace that reflected the coziness, quaintness, and history of Portland, and I couldn’t have found a better match than at the Francis.

As a history buff, I especially love staying in boutique hotels with historical background. I like feeling connected to that city’s history, and the Francis is part of the National Park Service’s Registry of Historic Places, guaranteeing its historical preservation for future travelers to enjoy for years to come. You are quite literally sleeping in the a historical piece of Portland. The new owners at the Francis have worked hard to pay homage to those who came before them.

Bit of History

Like most old edifices, this building has had a few identities through the centuries. The hotel is named after Francis Fassett who helped redesign Portland after the Great Fire in 1866. His set his legacy in brick and stone all over the city, and this building is part of that collection. His work around the city ,including the hotel, is now protected due to the city’s priority to preserve historical buildings, which keeps his influence alive and well over 100 years later.

How to Fall in Love with Portland, Maine

Francis Fassett built this home for Mellen E Bolster who had a dry goods shop and was man about town. The shop was named Bolster, Snow & Co ( take a look at that Victorian punctuation). The new owners of the Francis also opened up a restaurant titled just that (even though English teachers might cringe when they look up the place). I sadly did not get to eat at Bolster, Snow & Co but heard it was fantastic ( and a reason to come back).

It was later turned into a funeral home and then was vacant for several years before the new owners decided to renovate the building into a historical boutique hotel.

Decor + Details

Stylish history welcomes you at the front door. A 19th century mechanical clock welcomed me as I turn into the Francis off of the street. I later learned was made by Seth Thomas Clock Company, which is the oldest clockmaker in the United States.

I rocked up with more things than I had expected from the conference and felt like a bit of a bag lady as I walked through the beautiful brick building with a white columned entrance and into this sleek and modern interior.

The new owners of the Francis renovated the classic structure into a fifteen-room hotel with modern amenities ( and great wifi). An area of the building has been transformed into a spa, which I sadly did not have enough time to partake in ( but gives me a reason to return!).

The interior design of the lobby and lounge area had such a delicate balance between modern minimalism and Victorian charm. Tall windows allowed sunlight to pour into each room. Around the check lobby and waiting area, they had several charming and beautifully decorated chimneys that not even Santa Clause would want to come down and dirty the place in soot. Stain glass windows complimented the minimalist photography done by Nicole Wolf, a local photographer, and bright bouquet of pink dahlias and roses gave each room a pop of color.

I loved all of the photography around the space, and the lovely attendant, Alex, caught me staring at it. She told me that the hotel was doing an exhibition of female only photographers ( 2 points for Beyonce).  

My Room

I walked into my room and quickly reconsidered my plans for the day- did I have to go to this conference and network with people? I would have much rather starfished out on my giant bed and forgotten about any self-imposed obligations.

I was given a corner room with a view of Tandem cafe across the street ( which I will get to in a minute) and to my right was a view of the rolling hills and pine trees of the countryside in the distance. It reminded me that I wasn’t too far from getting lost in the woods if I wanted to. I had views of the roofs of the surrounding houses where people had decorated with lawn chairs or gardens growing on top of them. This is a place and a people that clearly can’t get enough greenery and sunshine when the opportunity arises.

My room had beautiful play between historical architecture with a modern cover. It had more than enough room for me to get work done on their desk and do yoga in the morning ( something I have to do whenever I am traveling). In one corner was an intricately decorated chimney with one of the Nicole Wolf paintings hanging above it. I was swimming in natural light and didn’t need to turn on any lights until the sun had completely set.

The bathroom had a lovely array of Malin + Goetz fancy soaps ( I wish I smelt like cucumber + cilantro all the time). Although I was full from my conference, they had a fantastic selection of locally made food products from cold brew to chocolate and chips. I looked at them in longing but my stomach begged me to be gentle with her since - next time.

Alex brought me to my room and explained the layout to me. Before she left, I playfully asked her if she had ever seen a ghost or if there were any ghost hauntings rumored in the Francis?

“Well since it was a funeral home, the ghosts are already dead. So. they haunt the place they died in, not the funeral home.”

That was totally sound logic.

If only my home in Brooklyn could have been this nice.

I sat down on the bed felt the weariness of my travels and clothes tumble to the floor as I laid down and put on one of the spa robes hanging by the door. I wondered why I denied myself such a simple luxury back home.

The Location

I sadly had to spend more time out of the room than I would have liked because of the conference. But as someone who loves to walk, it was a perfect location in the city. Nestled in the fancy West End neighborhood, the Francis was a 10-minute walk away from the city center. So it pushed me to go through a less explored and more residential part of town, filled with gorgeous Victorian houses, ivy strangling the brick buildings, and magnolia blossoms flaunting themselves to the world for the first time in a year. Even though I felt busy, the walk reminded me to slow down and enjoy the last place in America that spring was kissing.


I was surrounded by the rusty red buildings nearly everywhere I walked.  The homes and edifices aren’t vibrantly colored or slathered with street art as other cities are turning towards. Portlanders keep their art indoors.

Regardless of its simple facade, Maine has a long connection and history with artists coming and working from all over the world. I mean, it is a quiet spot to get your art done for one, and who wouldn’t be tempted to capture the natural diverse landscape around you? I resisted the urge to purchase an easel and canvas and just paint by the sea all weekend. It is still a hub for experimentation and advancements in aesthetics, techniques, and individual practice. So I can understand that with not many people around you to distract you, you are bound to get your work done.

Portland Art School is conveniently located in the city’s main street with fresh blood and ideas pumping art out of the heart of the city. There are over 80+ galleries and museums in the city center alone.

And where there is art, comes the unique characters that are attracted to it. It has its fair share of eclectic art folk. I saw a man in white overalls, sombrero walking a tiny little dog ( and it wasn’t Cinco de Mayo) to couples dressed like they just walked out of an LL bean magazine but with electric blue hair.  Although Portlanders are constantly telling them that are not where Fred + Carrie live, it certainly can be just as weird.

Friday Art Walk

The most comprehensive way to experience all of Portland’s art scene in one night is the Friday Art Walk. It is a night where the city truly came alive ( meaning there were more than 5 people on the street at one time).

It was a bit of a chilly day, but that didn’t stop Mainers from getting out and socializing. My old roommate from Portland once told me that Mainers don’t let the weather get in the way of their plans. She would often have to go to school after Mother Nature blessed them with three feet of snow the previous night. In a land of eternal snow, she could count the amount of times she had snow days on two hands from Kindergarten to graduation.  

Although I’m from upstate New York, I still hate the cold. So, I hopscotched from one gallery to another, which seemed to be as popular as bars are in the Czech Republic or taco stands are in Mexico City- you could see four others from the one you were standing in.

There was a wide range of contemporary art galleries, fine art galleries, and craft shops in Portland.  I took my time admiring the locally made art and crafts of New England while sipping on cheap wine and stuffing my pockets with cookies to save for later.

Out of all of the galleries I visited, my absolute favorite one was the Mainly Maps, Framing, and Gallery.

It is run by a swarthy local named Leo, who used to be a professional clown  ( I’m not kidding). He looked like he was born and aged by the sea. His face was framed with a well trimmed white beard, and his skin was red from spending many hours squinting against the sun and reflection of the water. I have no idea if this was his real history- but that is the kind of person he looked like.

The expansive room was filled with maps of every type, color, and style. It gave me the same anxiety that a bookstore does: that there simply isn’t enough time to explore the whole world.

He had the most perfect Maine accent- not as harsh as an accent from a Boston construction worker but a straight shooter. He had the confidence of a man who had seen death and didn’t blink.

“Haave some cheese or wine,” he offered as I had already finished pouring my glass.

I complimented his store and told him I was a travel writer.

“Ah well if you like this, then yah haave to go down to the basement. You’ll love it.”

I grabbed a few slices of  Cabot cheese ( the high brow/ low brow cheese of New England) and store bought pepperoni and made my way down.

The basement was filled with eclectic and one of a kind artwork from his collection: old posters, more maps, rare artwork from local artists.

I came back up and we started talking about travel. He sat back in his chair and offered me more wine, cheese, and recounted his brief visits to New York. With his voice, he could have read spam emails to me and I would have been endlessly entertained.


541 Congress St

Portland, ME 04101 Arts District, Old Port


Monday- Saturday 10:00 am - 7:00 pm

Sunday  12:00-5:00pm

Some of the other places I didn't get to check out but wish I did was

Portland Art Museum- focuses more on artists from Maine and America like Winslow Homer, Edward Hopper, Louise Nevelson and Andrew Wyeth, overall but includes its lionized painters like Monet, Degas, Picasso and Renoir.

Maine College of Art- the oldest school in Maine several galleries and opportunities to tour the art studios around the year.

Portland Art Gallery- a large art gallery that showcases Maine artists.


Matilda, Hermione, and Belle were all characters that I STRONGLY identified with as a child. I have yet to grow out of my love of books and bookstores ( and to this day still need to read myself to sleep or else I toss and turn).  

Needless to say, bookstore culture is the one thing I seek out ( and love getting books in other languages, even if I can’t read them...yet). Within my first musings of the city, I noticed its multitude of bookstores, possibly too many for me to go through in a single weekend.

Let’s go through what I was able to scavenge through.

Yes Books

On my first day there, I dipped into Yes Books to get out of the cold and start getting some feeling back to my fingertips ( why, WHY, would I pack gloves in MAY!).

I opened up the door and was hit with one of my favorite smells: aging paper.

I don't know why all used bookstores have that smell: the fermenting of parchment, the wood covers deteriorating, the tenderness and skin cells left by each previous owner imprinted on every book.

I realized that the store seemed pretty true to its name in that YES books are here, but you have to do the searching for what you want on your own. The most uptight librarians would have a heart attack if they saw the schizophrenic upkeep of the store.

There were “labels” of each genre, which gave me some sort of direction, but there were also just random towers of books that ate away at the walking space. Only if you asked the man at the desk, in his flannel would he know if he had something- the catalog was conveniently located in his brain. If there was a method to the madness, few of the visitors could see it, but I still found it fun, nonetheless.

This isn’t the kind of place you go to if you want to get in and out. Due to its minimal curation, you need to dedicate at least seven hours to really get a feel for this place. It is the kind of bookstore where you want to spend long hours musing and buy just what looks interesting and is enough with your pocket change. Because I didn’t know what I was getting into, I was a little defeated because I didn’t have that kind of time, but it felt good to just rest my brain and warm my hands for a bit.

There were a few moments where I thought the towers of books seemed a bit wobbly. If they all collapsed on me, it would take a few days for firemen to find me. So, explore with curiosity but caution.


589 Congress St

Portland, ME 04101

Arts District, Old Port, West End


Sunday- Monday 10:00 am - 6:00 pm

Green Hand Bookshop

Another fantastic used bookstore, Green Hand is the organized older sister to Yes Books. Unlike the used bookstores where it is disorganized and you open a book and a moth comes out, Green Hand keeps their books ( and hands ) tidy. This used bookshop in Portland is highly curated and has an impressive stock in nearly every genre. It specializes in more unique, rare books, with an eclectic mix of fiction, especially in horror and sci-fi.

The woman who owns it, Michelle, seems to have had a brain enhancement to maintain so much knowledge about books. She is like a human algorithm,  “Oh if you like Nabokov then you would probably Camus, Marquez, and Joyce! She is highly knowledgeable about literature and authors in all genres ( I could have spent have of my time talking to her).

The book cute french postcards tucked away in little corners, which always make good bookmarks.


661 Congress St

Portland, ME 04101West End



Print: A Bookstore

I passed by Print when I was driving with my old roommate to go visit the Portland Head Light and Fort Williams Park and begged her to pull over.

I saw the tall windows with the name painted inside in lovely font and immediately wanted to roll out of the car and into the bookshop. Sadly we didn’t have time, but I dropped a mental Google pin to return.

Print is a great independently owned bookshop with new books. It has been named one of the best independently owned bookstores in Portland. They have a great selection of contemporary pieces and the classics but really put an emphasis on Maine authors and locally printed works. Their displays have a clear art and activist edge. Although I didn’t get to attend, there seems to be public readings happening nearly every week. It seems like a great bookstore that is trying to build more community.


273 Congress St

Portland, ME 04101East Bayside


10:00 am - 7:00 pm


Coffeeshop culture is a common area that is reviewed when visiting a city ( my addiction is telling me to write this in an attempt to normalize its impact). But coffee shops truly are my happy place. Whenever I am tired, need to rest, be a little introverted, or get an energy perk, coffeeshops are the way to go. I was able to review some of the best coffeeshops in Portland, and as the digital nomad I am trying to be, these coffee shops were especially great work in or study in.

Tandem Coffee Roasters Portland

Tandem was one of the first places I found. Well, I was lead there in a sense. I came across it because, first, it was across the street from the Francis, and, second, I was low key stalking a corgi. I had seen this four-legged friend be walked in the same direction as I was heading as I moved away from the bus station and through this misty city. The moment I saw its stump legs waddle away from me, I vowed I would pet that corgi. Yes, I am proudly a corgi lover, borderline obsessive. I can spot their gate out in a of crowd of dogs and will pummel them out of my way until I get to the breed that is only good enough for the Queen.

The corgi and its owner were walking a good distance up ahead of me but fortunately the streets rarely have more than 3 people on it at a time, so I had a consistent clear sight to stalk, I mean, see the corgi.

The girl walking the corgi paused in front of a building that looked like it used to be a gas station because of a solitary awning where one probably  used to stand under to avoid the temperamental Maine weather as they put gas in their car. Now it was allocated to shading hipsters on picnic tables scarfing down a cinnamon roll and espresso.

The walker slowly started tying the dog up outside, and I casually ( frantically) came up and asked to pet her dog as she clearly wanted to stop inside a beautiful coffee shop.

“Sure!” she said, “This is my coworkers dog actually, he isn’t mine.”

I had a Dorothy moment and realized I wasn’t in New York anymore. You are that trusting that you can tie someone else’s dog up outside and aren’t afraid of it being taken?! ESPECIALLY A CORGI!? There was too much trust in this town.

She stepped in as I gently patted his fluff and asked her what she recommended when she came back outside.

“Oh the cappuccino is great, but I love the chai,” as she slowly started untying the dog’s leash. I fought with every fiber of my being to not scoop the corgi up and start running towards the ocean.

“ I think this is one of the best coffee shops in Portland, at least in this area,” she said.

I made a mental note that this place was more than just for corgi hunting, but would be great spot to grab a morning coffee and then snuggle back into my bed at the Francis.

Tandem has two locations, and I only got to experience the one at the West End location.

It has lovely minimalist decor with tall open windows and white walls that were illuminated by the natural sun, which only shines through 4 out of the 12 months.

It was charming and the glass cases at the counter was laden with pastries and sweets that I could not touch ( I’m gluten free, sadly). They are quite glutones with their gluten: cinnamon rolls, scones, giant cookies, and muffins lined the counter like gems a jewelry box.  So, I just got a drip coffee ( WITH OAT MILK), which was perfect and not too acidic as I longed over the baked goods that would make my skin crack and break out like the Bolivia Salt Flats.

The stay and to go cups had silly little sentences all over them. I love a coffee shop with a sense of humor.

Reminder: Tandem was also across from the Francis and they have a special breakfast package where they will bring Tandem baked goods and coffee right to your door! No need to get out of those plush spa robes and greet the world yet.


742 Congress St
Portland, ME 04102



7:00 am - 6:00 pm

Speckled Ax

A local recommended that I try Speckled Ax’s coffee first. She said it was the only coffee that just made her happy! As if there was a clear distinction in her mood before and after having the coffee ( my thought bubble envisioned a *before* frazzled Cathy cartoon next to an *after* calm Cathy cartoon).

I was on the hunt for the uniquely named Speckled Ax (fortunately a short one since everything here is so close together). I look for coffee that gives me a thunderbolt of excitement that, for me, manifests itself as creative mania. That’s when the caffeine kicks in, and I start to believe that I am the most profound writer in the WORLD ( as she shoots up from her desk, coffee in hand, and spills hot liquid on her computer).  

I got to try it out on my last day, hoping I could have some energy to get work done on my 6 hour bus back to New York ( I don’t recommend taking the bus WHATSOEVER). But I figured this would ease some of the pain.

I walked into a well seated and busy cafe with Edison lights and dark wood seating. The place was crowded for a Monday morning, and people were busy clicking away on their laptops or discussing the newest art trend. Clearly a good coffee shop to study in or get some work done. I ordered an Americano and walked by all the roasting equipment, set up like beakers in preparation for a science experiment. Apparently, the coffee here is wood roasted, which takes longer to roast but keeps more of the flavor in.

As I paid for my coffee, I turned back and saw these beautiful speckled clay coffee mugs for sale and wish I had enough room in my bag to get one.

“Enjoy the sun today!” my barista exclaimed at me as he passed me my americano.

“That’s a rarity for you folks, isn’t it?” I said with a thick layer of New York sarcasm.

“Yup!” He gleefully exclaimed and continued and turned back to make another espresso.

Lord this place is sincere. That’s just darling.  

As I walked out and sipped my coffee, I started to feel some of that creative mania kickin’. It was a little more acidic than I anticipated but made my bus ride home much more tolerable.


567 Congress St

Arts District

6:30 am - 7:00 pm

Bard Coffee

This was the only one I didn’t get to visit but wish I did. My local friend told me that this is a contender for the best coffeeshop in Portland, Maine.  I mainly wanted to check it out because it apparently does a pretty good Vietnamese coffee ( it’s just an excuse to drink caffeinated sweetened condensed milk. Hey, I’m not arguing with them). It is on the main stretch on Congress street, set in an old brick building with a fancy red arch way. On top of locally sourced coffee, they offer a lot of gluten options. Sorry, I mean range of pastries, sandwiches, and baked goods. The walls are covered in a pretty orange and white, breaking up the traditional bleached-white, minimalist decor all the Millennials go gaga for these days.  

According to their website, Bard coffee is as ethical as you can get. They have deep relationships with their farmers all throughout Latin America; the coffee is fair-trade and organic, and their roasting process is intentionally energy efficient ( mmmm I can taste the morality with every sip).

Please go for me and tell me how it is!


185 Middle St
Portland, ME 04101

Old Port


6:00 am - 7:00 pm

Let me know if this was helpful!