4 Days in Portland, ME 2018


Earlier this summer, Andrew and I decided that rather than get each other gifts for our birthdays, we’d save the money and go on a trip together. After browsing flights for a few weeks and brainstorming cities we’d like to see, we landed on Portland, ME.

First of all, round trip flights from NYC to PWM were less than $120 per person on JetBlue. The flight itself is only about 90 minutes total, and the Portland airport is a 15 minute ride ($10 Uber) from the center of the city. All wins in my book.

We flew in early Wednesday morning and stayed through Saturday evening. It’s definitely the off-season, but there is still plenty to do in the northeast in the fall, and 4 days was enough to see most things, although I could definitely stay for longer, especially during beach season.



We stayed in an Airbnb on the eastern end of the city. The decor was absolutely perfect, and Andrew and I took notes on how our host had decorated in hopes of someday replicating in our apartment. I’ve already purchased a few new plants.

Portland is a very walkable city, and from our apartment we could walk to the Old Port and the Eastern Promenade. We did walk to the West End a few times, but it was definitely a bit of a hike, and on chillier days we Ubered.

There are a ton of chain hotels right in the Old Port area, but when we were booking they were pretty pricey. That being said, the coolest looking one was the Press Hotel, which used to be the home of the Portland Press Herald. Such a cool concept!


We ate SO MUCH. I feel like I never hear about what divine food exists north of Boston, but every meal in Portland was truly spectacular.


When we first arrived in Portland, we went right to Tandem Coffee and Bakery to wait for our Airbnb to be ready, and to eat. I had a biscuit loaded with globs of butter and jam and an English breakfast tea. The biscuit was flawless, with the perfect ratio of sweet to salty to creamy to crumbly. They had other flavors, including an everything seasoned one, which I could be tempted to try in the future.

For an afternoon snack, Andrew wanted to get his lobster fix in at the Highroller Lobster Co., where he had a lobster grilled cheese, and I, very allergic to all shellfish, had a beer. The interior was so cute, and I could definitely see the place being swamped during the summertime. The staff was excellent, and even gave me a free half beer when the one I ordered kicked.

Since I had skipped the lobster lunch, by the time dinnertime rolled around, I was famished. We had both decided that Duckfat was a must-go, and decided to head over, since it was only a 10-minute walk. We arrived around 6pm and there was no wait, but it was a Wednesday night in October and the place is tiny. I have to imagine that during peak season the wait has to be pretty wild. I would say it’s well worth it, though.


We started with an order of the duck fat fries. Yes. French fries fried in duck fat. They were truly divine. We shared a small order which was plenty for both of us. For the main course, Andrew had a duck confit panini, and I had a Cubano one. Both were otherworldly.

Duckfat is also famous for their milkshakes, although after the fries and the panini, my body couldn’t handle more food. I can imagine though, that the fries and a milkshake might make a magical pair.

Thursday morning, we slept in and headed out to the Old Port area around 11am, where we stopped at The Holy Donut for Maine Potato Donuts. I was VERY apprehensive about potato donuts. Why ruin a great thing with…potatoes?


They were phenomenal. I had one cinnamon sugar and one Maine apple donut. I have been thinking about the Maine apple donut ever since. It was moist and dense and had the perfect cinnamon-apple flavor for fall. The donuts weren’t warm anymore by the time we got there, but I can imagine they are mind blowing when they are. Definitely worth going, even if you’re nervous about potatoes in your donuts.

That evening, we got dinner at Terlingua, which was literally around the corner from our house. We waited about 5 minutes for a table (like most places in Portland, it was tiny) and split the brisket and pork board, with a side of jalepeno cornbread. What we really wanted was the jerk chicken board, but they were out by the time we got there, which was only around 7pm. So if you want the jerk chicken, get there early.

The breakfast we had on Friday morning was really the pinnacle of the trip, though: Hot Suppa. They don’t take reservations, and are also pretty tiny, but since it was a weekday in the off-season, we only had to wait about 15 minutes for our seats. We sat at the bar, but it affected my experience 0%. I read that the wait in the summertime and on weekends is a little daunting, though. But worth it.


I ordered the Mother Clucker, which consisted of a big biscuit with a big piece of fried chicken and a big scoop of sausage gravy and cheese curds. It was like biting into heaven. The chicken was juicy and spicy, the sausage gravy salty and creamy, and the biscuit melted in my mouth. I made Andrew walk the mile and a half back to our house after eating, since I felt like I had just ingested a bowl of paper mache. Andrew, having eaten an entire serving of chicken and waffles, felt the same.


Saturday morning before we left, we stopped at Dutch’s. It’s a counter service place where you wait in line to order, then seat yourself and they bring your food to you. We rolled up around 11am and waited a good 30 minutes to order. This time, we both ordered fried chicken biscuit sandwiches, although Andrew added bacon to his. While the sandwich was delicious, it was slightly overshadowed by the Hot Suppa one from the previous morning. By a slim margin, but someone had to be the loser here.


The amount we drank rivaled the amount we ate. Portland is a major beer city, but also had a bunch of wineries, distilleries, and even a meadery (we did not go there). All told, we must have visited around 5 breweries on Friday alone.


Aside from breweries, we also went to a few cool bars. We went to Novare Res every night after dinner. It was a cool, historic vibe with tons of different beers and staff that knows their stuff. Also could definitely be haunted.  I might have even felt a chill from a ghost, but who really knows?

Whenever Andrew and I travel, I’m obsessed with finding speakeasies. There’s usually at least one in every city we go to. What I like more than just a hidden bar with expensive cocktails is a hidden bar where a drink won’t set me back $20. Lincoln’s had everything I wanted. A secret and hard to find entrance plus a menu with nothing over $5. They only take cash, but there is an ATM outside the door…if you can figure it out.


And then there were the breweries. The most famous one I was eager to see was Bissell Brothers, which was in a huge, beautiful facility on the West End. In the same plaza is also a winery and a distillery. I even managed to drag Andrew to the winery (Cellardoor) for a post-beer tasting.


About 20 minutes outside of the city (a $15 Uber ride) is Industrial Way, where there are warehouses filled with breweries, wineries and distilleries. The most famous one is Allagash, although we didn’t stop there.


We made our way through Austin Street, Battery Steele, Foundation Brewing and Definitive Brewing before finally calling it a night. Everything is super close together with outdoor seating areas, lots of good dogs, and food trucks, so it’s easy to hop around and try different things. Depending on the brewery, the small 5oz pours of each beer ranged from $2- $4 each, making it too simple to try several at a time.


While most of the breweries specialized in the ultra-hazy, juicy New England IPA’s that we love, the best beer I had that night (and perhaps best beer I’ve ever had period) was Stuffed at Definitive – a stout brewed with Oreos. It was like drinking a chocolate marshmallow, which I suppose is exactly what an Oreo tastes like. They only brewed a limited amount, so only small 5oz pours were allowed. Although that did not stop me from having a few. Unfortunately, it kicked the next day, but I’d count on Definitive to keep brewing up the good stuff.

The final recommendation I have didn’t fall into any of these categories, but we did stop into Longfellow Books (twice). I love books and booksellers, and especially love to see the stores I’ve worked with for years and haven’t got to see in person. Such a charming shop with lots of excellent books. Support local booksellers!

Whew! It was a short but amazing trip. There’s still plenty of Portland left to explore, so I’m excited to go back sometime soon, hopefully in the summertime.


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