Boston Area Escort, Confidante, and Travel Companion.

Dating Guide: Portland Maine

Portland is one of my favorite cities to visit, I try to make it up there at least twice a year. I feel like I’m often telling people to visit Portland for a weekend, it has so much to offer and I’m not sure everyone is sold on my rave reviews. Regardless, I have a few favorite joints I like to frequent on my journeys up north so I thought I’d share them with you. 

Coffee & Snacks 

TANDEM 

This place is fantastic and in my opinion, no trip to Portland is complete without a mocha and a baked good from Tandem. I highly recommend trying one of their biscuits (the cacio e pepe one is life changing) or their unique pies. 

Hifi Donuts 

Now I know this isn’t the first place to come to mind when most people think “Portland” and “Donuts” but it’s truly the superior option. I’m always overwhelmed by the delicious offerings but the blueberry ones are tops in my opinion. Their sandwiches are great too! 

Standard Baking Company

This place often has a tremendous line but it’s baked goods will remind you that life is pretty sweet. Their breads are like none other and their chocolate chip cookies are substantial. It’s definitely worth the wait and worth cheating on your diet for. 

Funsies

Round 1 

I was first exposed to this Japanese chain of Dave and Busters type arcades in Los Angeles, I had no idea at the time that we even had any in the northeast but we certainly do! This place is chock full of nostalgic games as well as new imports (some not even translated to english yet) and you can spend hours here. They also feature private karaoke suites, bowling. darts. and billiards.

Coast City Comics

I always visit this place when I’m in town. As some of you know I’m quite the fan of comics and this place not only has a jam packed recent releases section but a pretty sizable collection of back issues. There are scads of collectibles plastering the walls but I can’t speak to the selection as I’m usually engrossed in the comics. 

Yes Books

I discovered this place while meandering on Congress Street, burning time while waiting for a friend and I’m so happy I stumbled upon it. If you’re a book lover, the place may be overwhelming as there are so many books in one business! Things are organized by genre but you still have the novelty of not exactly knowing what treasures you will stumble upon since they are mostly used books. They have a ton of fantasy offerings and there never seems to be enough time to look at all of them but you are bound to find something to make you feel nostalgic here. 

FOOD

Duckfat

I feel like Duckfat needs no introduction, it’s the place most Boston and Boston adjacent people seem to namedrop whenever I bring up Portland. It’s a pretty great spat for an afternoon meal. I love their sandwiches (their take on the BLT is a must for me every time) and of course, everyone loves their poutine. 

Empire

This isn’t your usual Chinese joint. From unique offerings (Duck Fried Rice? Please and Thank you) to every dish I’ve tried making my tastebuds sing, this place is one of those you have to experience to believe. Prior to the pandemic it was practically impossible to get a seat here and now it’s take out only which is pretty great because it makes the food more accessible. 

Scales

After going to Portland a few times I kept hearing people mention Scales so I made it my business to try it out. The pictures of their dishes online looked fantastic so I visited one evening and was not ready for what would become a life changing moment. Their fish dishes are beyond belief and masterfully prepared, and their non fish dishes all sound incredibly seductive (I’ve not strayed from the fish so I can’t say for sure). This place has secured itself a spot in my shortlist of favorite restaurants and I love going here with a charming companion. 

S.