In a sea full of foodies, the city of Portland is a bright beacon.
“We need to pace ourselves.”
This was the mantra for the day and had already been repeated 7 times before rolling into Portland, Maine’s city limits. The artsy “Vacationland” metropolis has a positively booming culinary scene, and I was pretty hungry. With only one full day to stuff myself silly, I knew strategy and stretchy pants were going to be key.
Here’s how to eat and drink your way through Portland, Maine in 24 hours.
(There are plenty of eateries and drinkeries I had to leave out for sake of time, but that just means future versions of this exact post.)
Before we slap on our maternity pants for the impending food baby, let’s talk about where to sleep off all of that delicious fare. The centrally located, nautical-themed Portland Harbor Hotel will have you walking in relatively close proximity to everything in the downtown Old Port area, while other cool neighborhoods are still well within reach. I slept like a very full baby in one of their newly renovated rooms.
Now let’s eat.
12PM: LUNCH
Bite Into Maine @ Allagash Brewing
It’s no secret that fresh lobster is Maine’s pride and joy. Indulging in a classic lobster roll obviously had to fit into this 24-hour eatfest itinerary, and why not have it be numero uno on the list?
Bite Into Maine has a solid reputation for making some of the best of these buttery-mayonnaisey beauts and I had no problem being the judge of that. In season, their trio of food trucks are in and around the Portland area, but in the winter, just one posts up at none other than Allagash Brewing (famous food truck meet famous brewery, boom).
I marched right up to the window and was delighted to see three different lobster roll options (Maine, Connecticut, and Picnic style) AND that you can get a flight with a miniature version of all three options. I went with the classic Maine lobster roll because I love mayo, and opted for the 6oz. of lobster stuffed in there, because WHY NOT. (It was worth it.)
TELL US HOW IT WAS:
Um, delicious. Slightly toasted buttery roll, heaping lobster with the perfect amount of mayo, and chives for a bit of zest. It was probably one of the best lobster rolls I’ve had, and totally worth the price tag ($34 for the 6oz). I washed it down with a beer that was good, but I would’ve preferred to wash it down with another lobster roll, if I’m being honest. But, pace yourself.
1:30PM: SNACK
HIFI DONUTS
Every good food itinerary needs a donut stop. Enter, Hifi Donuts.
Prepare to drool.
With three donut types (crullers, cake, and yeast) and a load of brilliant flavors, you’ll be hard pressed not to find something you like. I snagged a half-dozen of these bad boys to taste here and there, when I wasn’t eating something else in Portland.
TELL US HOW IT WAS: The honey-dipped cruller, Mexican hot chocolate, lemon poppyseed, and calico glaze all blew my New England socks off.
2:30pm: Mid-day snack
The Shop by Island Creek Oysters
Ah, oysters. You either love ‘em or you hate ‘em. I happen to love them and was ready to slurp down some of these notoriously delicious New England oysters.
The Shop By Island Creek Oysters in Portland’s East Bayside neighborhood fulfilled everything I was looking for - quick, fresh, and adult beverages at the ready. They make a killer Bloody Mary, topped with a…you guessed it, OYSTER. And, although my pants were getting tighter by the minute, these would, at least, be not too filling.
TELL US HOW IT WAS: It’s the type of no-frills place that works — fill out your oyster-ordering card, drop it at the counter, saddle up to a table, and enjoy. ENJOY I DID. (I hope you read that last line in a British accent, because that’s how I typed it.)
4:00PM: MID-DAY SNACK x 2 (and dranks)
DIRTY DOVE BAR
A dive bar is a must for me in any town or city and Portland’s newest bar fit the bill nicely. The Dirty Dove in the East Bayside neighborhood is a funky mix of speakeasy-dive bar with elevated and imaginative cocktails + bites, where everyone is welcome.
A booklet housing a seasonal menu, house rules, and prose reminiscent of refrigerator magnetic poetry is a breath of fresh air. A pocket-sized kitchen puts out very tasty small plates, while solid jams play in the bar and a tiny Etch-A-Sketch or Lite Brite entertain you, 80’s style.
TELL US HOW IT WAS: Fun, delicious, and fun. I can vouch for the Mystic Cheetah cocktail, fried chicken sandwich, and fish croquettes. Great, now I’m drooling just thinking of them.
6:00PM: Pre-Dinner Sweet Treat
Gorgeous gelato
Cleanse your palette with a refreshing scoop of gelato, because why not? Gorgeous Gelato is located just a hop ‘n a skip from The Portland Harbor Hotel, putting you in the perfect position to freshen up before dinner at the onsite restaurant. This cute lil shop brings a little bit of Italy to Portland with legit gelato in a whole slew of flavors like lemoncello, bacio, and hazelnut.
TELL US HOW IT WAS: I ordered the scoop duo of ‘gorgeous’ (vanilla with chocolate chip and caramel) + pistachio. They were both creamy, but the ‘gorgeous’ flavor won, in my book.
8:00PM: Dinner
Blue Fin Restaurant @ The Portland Harbor Hotel
As long as your following the day’s mantra of pacing yourself, you’ll have room for dinner. Good news is that you don’t have to venture too far - Blue Fin Restaurant at The Portland Harbor Hotel is just what the foodie doctor ordered.
The cocktails were refreshing, the bartender was super friendly, and the menu features dishes that are basically Maine-on-a-plate…and, extra points for the super comfy bar stool-chair hybrid.
TELL US HOW IT WAS: I had the lobster ravioli and it did not skimp on the lobster. Pillowy pasta filled with cheese and lobster in a cream sauce? It was reaaallllllllllllllllly good (that’s like 17 l’s in “really”). The steak hit the spot too; cooked to perfection.
9:30PM: Craft Cocktail O’Clock
Blyth & burrows
Don’t worry, no food here (although they serve it). Cap off your night with a craft cocktail at Blyth & Burrows on Exchange Street. The inventive menu will turn you into an adventurous drinker and the ice cube formations will leave you wondering, “how in the world did they do that?”
TELL US HOW IT WAS: I was more impressed by the diamond-shaped cube of ice than the drink itself, but perhaps I just chose the wrong one. Bonus points for the Kung-Fu movie + Wu Tang music combo in the back bar though.
8:30AM: Breakfast
Becky’s diner
Hopefully you burned some of the previous day’s calories whilst you slept in the comfy-cozy hotel bed. Because, breakfast at Becky’s Diner awaits. Becky’s is a Portland staple, which means it’s good, but also that it’s a busy place. You’re probably going to have to wait for this quintessential diner experience, but you’ll likely wait at any of the other popular Portland brunch spots, if it’s a weekend. They’re known for their lobster omelette, pancakes with wild Maine blueberries, and eggs benedict. We tried two of those three.
TELL US HOW IT WAS: It was quick service, plenty of coffee, and everything tasted pretty darn good. If you get the pancakes, do yourself a favor and ask for the real maple syrup - anything else just isn’t going to cut it.
11:00AM Lunch (part one)
Central provisions
Three words: MAKE. A. RESERVATION.
It’ll be worth it. Central Provisions is smack dab in the Old Port section of Portland, slinging small plates with locally sourced food, and tasty cocktails in a historic building. It’s cozy and the menu is designed to dazzle…dazzle it does. I had heard through the interweb grapevine that the Baja Fish Sandwich was something to be had — I can confirm. Perfectly cooked fish is the star of this delightful sandwich, paired with some unassuming pickles that actually blew my mind, they were that good. Wash that down with the Brown Derby cocktail and you might just live here now.
TELL US HOW IT WAS: This is probably my favorite place of the whole 24-hour food tour, if that gives you any indication.
12:00PM: Lunch (part two)
Gilbert’s chowder house
I know, I know, you’re full. I was too. BUT HEAR ME OUT — this is quite possibly the best clam chowder I’ve ever had, so if you can’t eat it as second lunch, get it to go.
Disclaimer: I have no photo of the actual chowder because I was excited and ate it all before remembering.
TELL US HOW IT WAS: See above statements.
Notable tips:
bring a food-loving partner in crime and split dishes to avoid that over-full feeling.
Take a nap if you need it.
Bring stretchy pants, seriously.
Walk around as much as possible.
PACE. YOURSELF.
And that, folks, is how you eat (and drink) your way through the foodie city of Portland, Maine in 24 hours.
Now if you’ll excuse me, I need to go fix myself a salad for the foreseeable future.
Disclaimer: This blog post features a few places that were in collaboration/hosted, but rest assured it was all carefully curated and opinions are all my own.