Last week on a twitter thread from The Clock Out, it was mentioned that readers may like to see local guides to different cities. Well I am not much for a world traveler (I have been to India, however) so I can’t offer judgement on a ton of places. If there is one thing I do know, it is Portland, Maine. I can’t say enough about this little city. If it wasn’t so damn expensive to live there (relatively speaking), the Mrs. and I would consider it. However, we like our little plot of land and the privacy that comes with it, so that won’t be happening anytime soon. Instead, we make the trek into the Portland area on a daily basis, including most weekend days, because there is always something to do in Portland.
Portland is not exactly a destination for a week-long trip, but if you are out there debating the next city to take a trip to explore on a long weekend, I recommend you come check out to the city of Portland. From the working waterfront to the parks of Deering Oaks and the breweries littered throughout, there is plenty to explore.
This will be a multi-part series covering food, drink, sights, and activities. First up, let’s talk about food. I will be giving only a few places for each meal so that this thing doesn’t turn into a full-blown novella.
In the spirit of transparency, I must admit something. I flat out do NOT like seafood (for the most part.) I know, I know. Right off the bat you’re thinking, “Why the hell is someone who doesn’t enjoy seafood giving a food guide to a city known for its fresh seafood?” Well, the simple reason is because I want to, and someone was foolish enough to give me admin privileges for this blog. So, buckle up. I have included several spots in this guide upon the recommendation of some of my friends, so if it is beasts of the sea you crave, there are a couple spots listed that you should check out.
Let’s talk about breakfast.
If it is only sustenance you crave, then these are the spots to hit while in town.
Miss Portland Diner
This sweet little spot on Marginal Way near the back-bay offers your classic breakfast menu and is one of my favorites. There is not a lot of seating as this diner is the old-school trolley car style diner so it’s best for smaller groups. Nothing fancy, just well-cooked breakfast food and plenty of it. I highly recommend the shamrock omelet.
If nothing else, you must go there because of the slogan. “Becky’s Dinah, nothin’ finah!” They have gargantuan pancakes, and everything is cheap as hell so try it all. This spot is also one of the only places on Commercial St. you won’t have trouble finding decent parking for!
The Holy Donut
This isn’t necessarily a breakfast spot unless you consider only eating donuts “breakfast.” Which I do. And hoooooo boy do these donuts rock. These things must weight close to a pound and they are greasy, dense, delicious freaking donuts. If you don’t stop in when you’re in town, you’ve done yourself wrong. The chocolate sea salt donut arouses me.
If you are looking for a bit of a boozy first meal of the day, check out these two spots.
Their bloodies and mimosas are the bombdiggty. Their food is even better. It’s greasy, it’s comforting, and it’s a little quirky. The line will undoubtedly be out the door on any given Sunday, but it is absolutely worth the wait. Go here.
The menu here is not terribly overwhelming. It is simple, a little on the pricey side for breakfast in my opinion, but the drinks are excellent and it’s a cozy little spot. I went here for a New Year’s brunch a few years ago and it is one of my favorite brunch memories. The only downside is sometimes parking is a bitch. I hate parking on Congress St.
Alright so you’ve walked around a bit, maybe you went to the park and checked out the farmer’s market, and you are ready for lunch. Here are three spots that I (and several others) recommend.
Gilbert’s Chowder House
Fittingly, this place is known for its chowder. As mentioned previously, I hate seafood. But I love me some clam chowder for some reason. This place has the best chowder you will ever have, and I’ll not be convinced otherwise. It also boasts a nice little patio to enjoy your meal outside if the weather permits. Get the bread bowl of clam chowder and then take a nap.
It’s probably a little weird suggesting a pizza place in Portland, Maine, but this pizza is fantastic. Thinner crust, specialty pizzas like the pulled Pork & Mango or the Mashed Potato, Bacon & Scallion never disappoint. We get these giant pies at work frequently and they are honestly part of the reason I like my job so much. If you’re not looking for a whole pie, at least stop into the Congress St location and grab a slice for a snack.
The Highroller Lobster Co.
What would be a guide to Portland, ME without including a recommendation for a lobster roll? Although they are repulsive, bottom feeding ocean bugs who literally eat trash, people seem to be obsessed with Maine Lobster. Some people say these lobster rolls are the best in Portland, so I figured I would include them. If you’ve never had one before, I’d recommend keeping to the classic that is just lobster meat and a little bit of mayo because that’s what a true lobster roll really is. I at least know that.
For dinner, I’ve included two spots I really love and a third spot that people rave over when people talk about Portland dining.
Great Lost Bear
GLB isn’t exactly “fine dining” which is why I find myself at home every time I go in. With a menu full of food that screams “you are fat, but you will enjoy this,” I’d plan on giving yourself some time to settle before going out for the night after eating here. It’s all reasonably priced, delicious comfort food. GLB also offers the best tap selection out of any place I have been to. Ever. With something in the neighborhood of 70 beers on tap and a bunch more cans and bottles, it is a beer drinker’s heaven.
In the heart of the old port you will find Timber Steakhouse. I took the Mrs. here for Valentine’s a couple years back and the steak was outrageously good. This is going to be a bit on the pricey side for a dinner, but the quality of product, the quiet, intimate atmosphere, and super friendly staff was one of the best dining experiences I’ve had in Portland. I still think about that ribeye every now and then.
Street & Company
Known for its seafood, Street & Company will be at the top of any list when talking about seafood dining in Portland, so I felt that I needed to include this spot just as I did with The High Roller. When clients come into town, the boss man takes them here. I can’t speak from personal experience, but the consensus is that this is the standard for dining when you are in the old port looking for salt water cuisine.
Portland has oodles of restaurants to eat at so if none of these places look intriguing, there is bound to be something that does. Remember to tip your wait staff, and I’ll see you next time for Your Guide to Portland, Maine Part 2: Drinks.