Just got back from a week visiting family in Maine and thought I'd give a few thoughts on where we ate.
Federal Jacks, Kennebunkport: Basic brewpub, a local hangout (since it's one of the few places open full hours year-round). Family friendly, great patio (overlooks the harbor). Fried clams were good, - big and well fried - everything else was pretty basic pub grub. Burger overcooked (nice brioche bun, though). Surprisingly few seafood options for a place right on the water. Great beer, of course (they brew Shipyard in house). Beware the antipasto plate - it's entirely deep-fried, and mostly consists of olives (very weird).
50 Local, Kennebunk: Looking for a nice meal out in K-port and Bandaloop (a former favorite) was closed, so we found 50 Local. Cozy location, friendly staff. Cocktails are creative and use a lot of local ingredients, but the bartender has a heavy hand with the sweet/syrupy and both of our drinks (bourbon with ginger simple syrup and cayenne, and a white sangria) were cloying and hard to drink after a few sips. Food was tasty but IMHO seriously overpriced. My seafood stew had a nice broth and a reasonable amount of fresh calamari, mussels, shrimp and fish, but wasn't superabundant and was $33 - for that, I'd expect more refinement and perhaps more than your basic inexpensive fish/shellfish (especially in Maine). Bill came to about $100 for two cocktails and two entrees - too expensive for what we got, but otherwise it was pretty good.
Eventide Oyster House, Portland - Service was terrible, we were ignored at the host stand for about 5 minutes (this is a tiny place and the hostess was about 5 feet away), then after being seated we were again ignored for about 20 minutes - everyone around us was looking around, wondering why there were 5 servers and cooks behind the raw bar just standing around but no food was coming out or orders being taken. Very strange. Once we finally got service, though, the food was extraordinary. Jumbo grilled oyster with Korean bbq and potato crisps was one of the best things I've eaten in a long time, and razor clam salad was also amazing - fresh, clean, perfect - and the oysters themselves were flawless. The "ices" that came with the raw oysters are a great way to improve on standard oyster accompaniments - I'd eat an entire ice cream cone full of the vinegar or horseradish ice no problem. Cocktails were also delicious (try the negroni blanco). Expensive, but unlike 50 Local it felt like the attention to detail and the exquisitely fresh food was worth it.
Pai Men Miyake, Portland: Highlight of the trip for me. Last visit we went to the "real" Miyake for the sushi tasting menu, and it was easily one of the top sushi meals I've had in a very long time. Pai Men is also excellent, but in a very different way - more an izakaya feel, less formal and warmer. Steamed pork buns were delicious, as were the yakitori (grilled skewers) of chicken heart, chicken thighs, and shrimp (though the shrimp did have a slight "off" flavor of uncombusted fuel, which is weird since they use a special charcoal that's supposed to emit almost no smoke). My wife's ceviche roll was outstanding and innovative (unlike standard sushi for sure), and my miso ramen was also excellent - not the best I've ever had, but a very solid rendition that had me finishing the bowl even though I probably shouldn't have. And after shelling out the bucks at Eventide and 50 Local, it was refreshing for a huge and fun meal with many different bites and flavors to come in at about $70 for two, including drinks.
Benkay Sushi, Portland: Our final meal was sushi at Benkay. Not a particularly nice ambiance; it feels a little dated, and neither the food nor the surroundings are anywhere near the dazzling perfection of Miyake. But the staff is friendly, and the fish was impeccably fresh. Chirashi plate was a huge portion of various sashimi and very well-cooked rice, and my wife's nigiri was all well cut and fresh. If they have the raw oyster special, skip it - the oysters get kind of lost in the sauce. Overall a good, if fairly standard, sushi experience. We had our 2YO with us, and it was a great place for that - no kid's menu, but they were happy to recommend stuff for her (she loved the agadashi tofu and the salmon avocado roll) and were all smiles. Not a destination place, perhaps, but we enjoyed it.
Will DEFINITELY return to Eventide (despite the service) and Pai Men Miyake, and I wouldn't say no to Benkay again (though I'd like to try some other places in town for sushi besides Benkay and Miyake).