The Worst of the Worst : Confessions of an Anonymous Portland Waitress

In my last post, I wrote about the customers that bring me joy, make me laugh, and truly make my job worth doing. However, dear readers, I’m sure you anticipated what was to come next. I can’t be nice forever because holy friggin heck this job sucks sometimes. So without delay, let’s jump into my list of the worst of the worst, the customers who occasionally make me wonder if I’m already dead and waitressing is simply my special punishment in hell. After reading, you can let me know if you think I’ll be serving until I’m financially solvent or if I should anticipate being here for all eternity.

[Read more…]

My All-Time Favorite Customers: Confessions of an Anonymous Portland Waitress

It’s hard to believe that July is here again and the Portland tourist season is in full swing! The summer months can be wild, uproarious, and occasionally painful for a server in Portland—and yet every year I seem to forget, and then I find myself doing the damn thing again. Which is how some women describe childbirth. Horrible pain, complete amnesia, and then—oh hell why did I do this again??

[Read more…]

Confessions of an Anonymous Portland Waitress: The Most Annoying Things Customers Do In Restaurants

In my last post, I revealed some of the best things about being a waitress, which is a kick-ass job most of the time. But there’s no doubt about it: Sometimes, serving is the WORST. Rude or high-maintenance tables can turn the joy of serving into a professional nightmare. In fact, you might be committing restaurant transgressions that are causing your server to curse your name and—don’t you doubt it—take her sweet time getting your order to the kitchen. So I’m here to help! The following is my personal list of the most annoying things customers do in restaurants. In a city where dining out is an integral part of daily life, every customer should learn how to act like an upstanding food citizen.

[Read more…]

Secretive Reality Show is Looking for Hip Portland Locals to Host


A new reality show is coming to Portland with the goal of sharing the often overlooked story of Portland as a home to young, thirsty, and single.  And as a city that offers them amazing and unique experiences through a world class food and drink scene. They are currently looking for two Portland locals to host the show. Try your luck. [Read more…]

Old Port Holiday Gift Guide 2016


We picked some of our favorite merchants in the Old Port and hand-selected items to help with your holiday shopping woes! There’s a gift idea here for every loved one and you can feel good about supporting local businesses! [Read more…]

T-Rex Takes Over Portland, Maine on Halloween 2016

Did you see the T-Rex take over Portland, Maine yesterday?! Don’t miss this video and Happy Halloween from Portland Old Port & Jared Saulnier.

The Portland Old Port Guide to St. Patrick’s Day

The Portland Old Port

Every year on March 17th, St. Patrick’s Day is a day to celebrate the color green, four-leaf clovers, and drinking (the latter evidenced by 6 a.m. bar-openings). Here are all of the events happening in Portland this St. Patrick’s Day! [Read more…]

Confessions of an Anonymous Portland Waitress

Confessions of an Anonymous Portland Waitress (1)

I must begin with the most terrible, most humiliating secret of all: I am a waitress! I am yet another overeducated, underemployed, late-twenties-to-early-thirties Millennial that, despite all the initial promise of my generation, has found herself trapped in the food service industry even though I am, like, way too old to being doing this. The TV soundtrack goes wah-wah.

But it’s okay! Thanks to years of therapy, in which I have dealt with the fact that I’m surely letting my pulled-themselves-up-by-their-bootstraps Baby Boomer parents down, and thanks to the last legal drugs for those moments when all that therapy fails, I have come to terms with the undeniable truth that I actually enjoy being a waitress. I like it so much that I’ve stopped skirting the issue when people ask what I do. A few years ago, I would answer, “Well, I’m working as a waitress, but I’m looking for something better.” Or maybe, “I’m a waitress, but I’m really working on my short story collection.” [Read more…]

Return To The The Escape Room

Part 2: Electric Bugaloo

Part 2- Electric Bugaloo (1)

Back in July the Portland Old Port crew was invited to be among the first visitors to the newly opened The Escape Room. In case you missed our first article, the premise is simple – up to 10 people are locked in a room and must work as a team to crack codes and solve puzzles in order to unlock the door and “escape” within the allotted 60 minutes. In our first go-round we came close…but failed. Just one unsolved clue stood between us and victory.

When The Escape Room opened they had one room, The Hunting Lodge, and one mystery – you are locked in a hunting lodge and needed to solve the clues and escape before the hunter returns. A few months later, they added a second room with a Stephen Kind theme and all-new puzzles. We were recently invited back to preview the newest room, The Bunker, which takes the place of the original Hunting Lodge room. [Read more…]

29 Ways to Ring in Your 2016 New Year in Portland’s Old Port


From 14-course tasting menus, to midnight champagne toasts from one of the highest vantage points in Portland – there is truly something for anyone looking to celebrate New Year’s Eve in the Old Port. With this many choices you are bound to find the perfect New Year’s celebration for you. If only finding the right date was this easy! [Read more…]