Acadia... you have to go to the Jordan Pond Tea House and have popovers and lobster chowder. It's a state law, you have to. Seriously, you'd be crazy not to. What we do is park there, do the ride, and then have lunch.
Jordan Pond House at Acadia National Park
Portland... Benkay is a sushi place at the edge of the Old Port on India St. I have been having the Deluxe Sushi lunch there for a decade. The sushi boats are also good. Micucci is an Italian grocery store up the street. In the back of the store they have a little place where you can get slabs of Sicilian style pizza. Ottos is one of those new wave pizza joints that serves things like potato pizza. Kinda fun, and perhaps a better choice if you kids are afraid of sushi.
Holy Donuts charges 2 bucks a donut. But if you want to know what a donut should be, you have to go try one.
Benkay Japanese Restaurant and Sushi Bar: Portland, Maine
OTTO Pizza : Boston/Cambridge/Portland, ME
The Holy Donut - 194 Park Ave and 7 Exchange St., Portland ME
I never miss Round Top ice cream when I am in Damariscotta. It's all good, but ask what's fresh, esp. the fruit flavors like blueberry. It's on 1A.
Round Top Ice Cream Stand - Ice Cream & Frozen Yogurt - Damariscotta, ME - Reviews - Photos - Yelp
One of my favorite places in Maine is Camden. There is a modest motel on top of the hill coming into town.
You can walk the town from there. We like Cappys Chowder House. There is a walking path up Mt Battie (it's a hill and not an especially big one). If you get up early, you can sometimes see the mist rising from the town and the bay. Very nice.
Cedar Crest Inn | Camden, Maine | Hotel Lodging Accommodations Rockport, and Rockland Motel
Another place we like is the Driftwood Inn. This is like stepping into the past. In the early days of car tourism, a lot of places where thrown together with what could be scrounged or bought cheaply. So the locations is great, watching the sun go down from the porch is something we love to do, and the food is really good. But everything is mismatched and the mattress prob won't be anything great. We love it.
Bailey Island Maine Hotel-The Driftwood Inn Maine Hotel, Hotel on the water near Brunswick, Maine
If you have a chocoholic in the family, try Len Libbys. The dark chocolate covered cashews are dangerously good, and make sure somebody tries the Needham ice cream, and try a bite.
Welcome to Len Libby