Portland Maine ~ Enter Through the Back Door – Part II The Old Port

The Old Port, Portland, Maine

Back in the 70’s when I was a young gal, our Saturdays were spent shopping downtown Portland.

There were no malls, no mega marts.  You parked your car on the street, put a quarter in the meter and walked and shopped, rain or shine.

Dad would go for his weekly hair cut at Jack Murdoch’s up above Congress street, and my mum, Brion and I would go walking from store to store.  We’d always stop in for a hot dog at Woolworth’s 5 & 10 lunch counter as our treat for “being good.”

As kids one place that was generally off limits was The Old Port.  Up until the late 70’s this area was a haven for rowdy fishermen, sailors and ladies of the evening.  It was filled with pubs and head shops, bikers and hard working folks.  Definitely not the tourist destination it has since become.

Fast forward to 1978, a wonderful and innovative bunch of folks decided to turn these old, decrepit rat infested buildings back into the Victorian gems they are today.   They primped and painted, remodeled and renewed.  They literally transformed this otherwise, “bad” area of Portland into a lovely haven for artists, musicians and visitors to the city.  And yes, there are still a few good old places to knock back a PBR with a local fisherman too!

So, let’s start by grabbing a pint at one of the Old Ports originals…

Three Dollar Dewey’s

“One Dollar Lookie Two Dollar Feelie Three Dollar Dewey”

Three Dollar Deweys                                            A Perfect Pint!

Three Dollar Dewey’s, “Portland’s Original Alehouse” is a Portland institution.  Originally it was up on the corner of Fore and Temple Street in the OP.  It outgrew it’s location and moved the lovely old, communal, picnic table style seating down to Commercial street and opened the new joint, years back.

Deweys has an amazing selection of drafts and bottled beer and some wicked good chowdah, nachos and chili!  So grab a table, a nice brew and a basket of warm fresh popcorn (self serve) and enjoy the waterfront.


Deweys Interior

The interior of Dewey’s is like a great old waterfront dock warehouse.  Warm wood, dim lighting and old brick walls.  There are large booths that hold about 6 should you want a more intimate gathering, or you can join the locals at one of the original large, heavy carved farm tables.

Good, though perhaps… not great food that is moderately priced.  I always found going for some beers and nachos was a good way to go.  But the kids always seemed to adore going to Dewey’s.  I still think it’s because of the atmosphere and popcorn!

241 Commercial Street
Portland, ME 04101-4622

Abacus Gallery

“What is art but a way of seeing?”  Saul Bellow

The Old Port has seen a lot of businesses come and go over the years.  Sadly, I think there are literally about 6 remaining that were originals from back in the day.

One of the mainstays in the Old Port is Abacus Gallery.

I always enjoy walking by Abacus’s window.  They have super rad displays with some of the most creatively colorful housewares, exquisite woven textiles, and some of the most amazing jewelery.  I know it’s easy to be intimidated by the word “Gallery” if you’re not loaded.  One would think that it’s stuffy, inaccessible, maybe even pretentious.

No.  Not this gallery.  Abacus is fun.  Abacus is friendly.  They’ve got customer service nailed down if you ask me.   I like that. I love their super low pressure, friendly,  laid back staff.  It’s perfectly fine to go in, browse and oooh and ahhh to your hearts content, even if you don’t purchase, though I’m sure they would be okay if you did buy a little something too!

And the coolest part….??

Abacus offers price ranges to work with many budgets as well; making their artwork so accessible to most everyone.  Though I’m still pining over their most awesome lighting that they have and at a cool $675. while TOTALLY worth every single penny, I may still need to  convince the Mr. that it’s all THAT!  See he’s more into computers and techie stuff, and me more the decor genre of stuff!  (see photo below of that totally awesome lamp I will own one day!)

One of their regular products that they carry is their awesome yearly calendar (shown above).  I love this calendar because it is meant to be framed as a piece of artwork, instead of the normal spiral bound calendar thrown up on a tack.


THE  lamp!!                                                                     Exotic Jewelry at Abacus

By the by… it’s worth mentioning that if you cannot make it to P-Town any time soon, you can still shop at Abacus online at


“A good film is when the price of the dinner, the theatre admission and the babysitter were worth it. “
Alfred Hitchcock


This post is  not for the tourists but the guys and dolls relocating to P-Town to save you years of searching for the great stuff around town!!

Where do you even begin when explaining the MOST AWESOME STORE EVA????!!!  Videoport is beyond and I do mean BE-frEaCkiN-YOND the greatest store of ALL TIME!  Get ready to give up your video subscriptions folks!!

Super bananas selection.  Super cool staff that know movies and can just give you a good idea if you’re stumped.  This is not and I MEAN NOT Blockbuster gentle readers!

So I’ll be lazy today and give you a review that I found on Videoport.  Only because I swear this dude Adam got into my head and wrote what I felt… Verbatim.

“Videoport is the best video store ever, period. A fantastic selection as mentioned including the Criterion collection, Foreign films, and Incredibly Strange! Every day you are eligible for a free movie rental. If you buy a movie from them you get a free rental credit. If you put $20 on your account they give you $5 free credit, put $30 on there and they will give you $10 free credit! Come on!


The folks that work there are great. They are have given me lots of background on movies I never would have known otherwise, helped me avoid wasting my time watching movies that just suck, and turned me on to films I probably would have never found otherwise. They will create lists of movies I should watch and remind me. They are the real-life Geniuses that Apple modeled their iTunes feature by the same name after.

Oh and its a local business, so your money is staying in town!”


151 Middle St  Portland, ME 04101-4391
(207) 773-1999
Open 10 – 11pm daily (can you think of any other place that has these freaking hours?? Nutz!)

Let’s walk across the hall from Videoport now!

Bull Moose Music

“If music be the food of love, play on. ”  William Shakespeare


I love this store!  It fondly reminds me of the old time, small music stores back in the 70’s & 80’s.  Great staff, great selection, great vibe.

If you are looking for some coolio new music, DVD’s or video games, this is your spot!

Rustic Overtones playing Bull Moose

Feeling a bit parched and hungry??  Yeah!!!

Let’s go to one of my favorite watering holes in P-town.  Ri Ra’s!

Ri Ra’s

“Few things are more pleasant than a village graced with a good church, a good priest and a good pub.”
  John Hillaby


There are really only a few, and I do mean a few authentic pubs left.  I have to say Ri-Ra’s has brought a bit of Ireland across the pond, to Portland.

I’ve never had a bad meal there and they truly know how to pour a perfect pint of Guinness.  So that is an epic win for me!

Their boxty …er “Potato Cakes”… are nothing short of divine… perfectly crisp, drizzled with balsamic, finished with green onions and sour cream.  OMG!

Mussels cooked in a whiskey garlic butter…. Come on!
Gimme a shot of Jameson with mine and I’m a happy lass!

Haddock with chips… Wicked!

Beef with Guinness Stew…. HUGE flavor!

Just make sure to order their chips with curry, just because you should.  Wow, these are something I can only hope to replicate in my lifetime!


It bears mentioning that during lunch you can only dine downstairs in the pub area and the water view is minimal (but the food of course awesome!).  At night you go upstairs and the view is OUTSTANDING!  In the summer months they open the large sliding windows to a gorgeous view of the harbor.

Do not.  I mean DO NOT let anyone fool you into going to DiMillos (the floating boat) restaurant. Ri-Ra’s is far, far better.

How do you find this amazing joint?  Walk straight through the Old Port toward the water and follow Commercial Street (that is the ONLY street that follows the waterfront of Portland) to the left.  Keep walking until you see the parking garage at the end of the road.

By the by…

There is a wicked GOOD pizza place behind Ri-Ra’s called Flatbread.   If you’re not wanting Irish food.  Definitely try them out!


72 Commercial Street
Portland, ME 04101
Phone: 207.761.4446

So if you go to Maine, you gotta bring home the lobstah! Where do you go???

Harbor Fish Market

“Is this chicken, what I have, or is this fish? I know it’s tuna, but it says ‘Chicken of the Sea.’ ”  Jessica Simpson


I must admit, I’m fond of the waterfront.  It holds my heart so tightly and will probably never release it.  That is okay with me.

I grew up on the waterfront of Portland.  I spent my summer days at the beach and spent a  lot of nights walking the shores.  It’s as much of a part of me as breathing.  Nobody truly understands it, unless they had it too.

When I was a young lass of around 16 or so I got one of my first real jobs on the waterfront working at Harbor Fish Market and to this day, it remains one of the BEST jobs I’ve ever had.  It soars above my interior design work which I have done for about 25 years and pretty much any other employment I’ve had.

It was a smelly, cold, wet, hard job.  But it was the most amazing thing I’ve done.  Truly.

They were some of the most honest, hard working bunch of folks, I’ve ever had the pleasure of working with.

So needless to say, I would be remiss if I did not mention the most awesome, the most amazing, the most… MOST gorgeous fish market in Portland, Maine.  Harbor Fish Market on Custom House Wharf.


The folks who work at Harbor Fish are real Downeasters.  So if you’re looking for a true New England experience, go there and have them ship you home some beautiful lobsters, steamers and mussels.  They’ll take care of you…wicked good!

9 Custom House Wharf
Portland, Maine

Retail Store Hours
Monday – Saturday
8:30 am – 5:30 pm
Sundays 9:00 am to 3:00 pm

Closed Most Major Holidays.

Lastly, I have to make notable mention of something close to my heart that you cannot miss… Especially on Sunday!

Brian Boru

The last great high king of Ireland.


Portland is filled with Irish and Scottish folks and I’m one of them!

I love a good pint of the black stuff or a double Jameson neat.   What I love even more is a good Irish session to go with that Jameson!

The problem with most Irish pubs is you go in there to hear good traditional Irish music and hear… well…
pop wank!

If I wanted to hear Beyoncé‘ I can sit in my car, thankyouverymuch!

Brian Boru has remains true to its roots.  Every Sunday afternoon they offer  traditional Irish sessions from 3-6 pm.  You can go in with the kids (it’s a pub… as in Public House, so kids are allowed before 6pm), grab some food and hopefully a place to sit your Irish a$$ and enjoy some great, great music.


It gets full fast!

Get there early to get a place to sit or you’ll be enjoying the Celtic music on foot.  Not as enjoyable, especially with kids!

These folks are 100% legit!

They show up with their Bodhráns, fiddles, Uilleann pipes and voices for a serious impromptu session every week and it’s nothing short of amazing to watch!  Good craic!

Look for the bright red building in the Old Port near the waterfront.

Oh, by the way…
Back in my previous life as an interior designer….
I assisted those boys with their color choice.  Hence, the iconic fire engine RED exterior.  I’m just sayin’.

Happy trails!

Stay tuned for next weeks post Portland, Maine ~ Enter Through the Back Door – The West End.

For Now: Check out Part I ~ Portland Maine ~ Enter Through the Back Door – The Arts District



3 thoughts on “Portland Maine ~ Enter Through the Back Door – Part II The Old Port

    • Hi there, Thanks so much. I accidentally posted it before it was completed. I’ve added more if you’re interested.
      Portland is a truly neat city! Very accessible, funky and friendly. I believe it has the most restaurant per capita (oddly enough!) too.
      Plenty to do, plenty to see and it’s beautiful year round. I recommend June or late September. Not so many tourists but still good weather!


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