My wife has family in the Portland area, and so we've visited for many years now. We used to come up 3-5 times a year, but now that my mother-in-law has moved back to the area from Orlando, we're coming up once a month. While there are plenty of pluses and minuses with that, one big plus has been our ability to try more restaurants. First caveat, my wife and I are big fans of Hugo's, but we knew even before they took the four month hiatus to remodel that we would need more places to eat, since we can't afford to eat at Hugo's every month! Here's a listing of what we've tried since the MIL has moved back.
Bar Lola - went during Restaurant week. We enjoyed the food and ambiance greatly, will return.
Miyake - Phenomenal sushi, the best duck taktaki I've ever eaten. Fresh out of the ocean uni, who could ask for more.
Grace - Beautiful room, very good food at reasonable prices. Had a veal sweetbreads in pasta carbonara prep which was wonderful.
Eventide Oyster - went for lunch this past Friday. Great oysters (though one shuckers hands were really shaking!). 2 orders of awesome fried shishito peppers, tuna tartare, fluke crudo, biscuits all top notch. Excellent cocktails as well. Another winner.
Zapoteca - Mexican - food was good, but we had some serious service issues (others in the room were also complaining, so it didn't seem to be just us). I'd like to try some more of their food, but I think we'll wait until more off season when they aren't so busy. The kitchen really seemed in the weeds all night.
Caolia's - great food and service. Had wonderful polenta fries with addictive cheddar sauce (more like spreadable cheddar), goat cheese and tapenade, pasta with pork/beef ragu, and paella. Can't wait to return.
Holy Donuts - completely wonderful bacon/cheddar, chocolate sea salt, chocolate cinnamon, Maine blueberry. All great. Plus they make the ice for iced coffee out of coffee, so there's no dilution as the ice melts.
One Fifty Ate - very good bagels, went to Scratch first, but they were sold out by 9:45 on Sunday Morning.
Q Street Diner South Portland - went with my wife's aunt and uncle for breakfast on Sunday morning. Great diner food, newly renovated since I last went there a few years ago.
Hugo's - First let me say that the wife and I are some of Hugo's number one fans, and we loved getting the eight course blind tasting. The new set up offers a five course tasting where you pick all your choices. The food was just as amazing as always, but we weren't as psyched about the vibe as in the past. They now have just 5-6 tables for parties of 3 or more. Everyone else sits at the bar. Now we are generally fans of sitting at the bar, but you don't interact with anyone behind the bar. Everything is brought form behind you, so you're constantly turning towards the server. The cost has risen a bit as well, since 2 people for a five course tasting with wine pairings will run you $300 before tip. It was always expensive, but now it's nearly impossible to eat there for under $300 per couple. I'll return as the food was still stellar, but I think we'll only go once or twice a year now.