Tour Maine Series: Portand + a Printable Guide!

This is my last post about from our recent trip to Bostom, Salem + Plymouth, and Portland. I saved it ’til the end because I loved Maine that much. It was absolutely perfect. Perfect weather, perfect views, perfect shops, perfect food, perfect everything.

It was probably one of my favorite places I’ve ever been.

I will say this: the ocean in mid-May is COLD. When we went lobstering our guide said the water temp was in the 40s! (But look how pretty!)

One of the places I recommend eating is the Lobster Shack Restaurant. The food is good (they have live lobsters right by the cash register), but the view is spectacular. I’ve never seen anything like it. Oh, and the whoopee pies are worth the trip to Portland themselves. Woah Nellie.

Most seating is outside overlooking the water. There are some tables inside, but you don’t go to this place to sit inside.

That’s a pretty fresh lunch right there.

And while we’re on the subject of food another must-do in Portland is The Holy Donut that’s in downtown Portland. C.’s favorite was the lemon, mine was the dark chocolate glazed.

We got to Portland around 5pm the day we drove in from Salem. Instead of stopping at our hotel we drove on through to Freeport (about 30 minutes north of Portland). It was the cutest town! We said when we come back to the area we might actually stay in Freeport. We only spent a few hours there and wish we could have stayed longer (we got Moseby his kindergarten backpack–that they’ll monogram while you wait–at L.L. Bean).

The next morning we went on a lobstering tour with Lucky Catch Cruises. I can’t recommend enough. They let you bait traps, throw them out, pull them in, etc. or you could just sit on the boat. I learned that I’m very fast at baiting them with herring. Maybe I should quit my job as a teacher and move to Maine and work on a lobster boat? Sounds like a good plan to me. (note: they accept cash or checks only)

One of our favorite things we did was explore the Maine coastline by getting off the interstate. We hopped on Route 9 outside of Portland and took it all the way to Kennebunkport. We stopped and visited the Bush family of course. 😉

And yeah, their compound was nice, but this house was my favorite in Kennebunkport. It’s on Haverhill Avenue and overlooks the ocean and it makes my little historic preservation loving heart go pitter patter. This is a house dreams are made of.

And then there’s this house on route 9. Yes, beautiful and old. …but look at the second picture to see its view: a pasture with stone walls with views all the way to the bay. You know when they built this home 200+ years ago the view was what brought them to this spot and I can just imagine looking across the street (where their barn is) and seeing your livestock (in my head it’s fluffy white sheep) grazing in front of the Atlanta. Wow. Just wow.

That night we ate pizza at Slab back in Portland. The pizza was great, BUT they won’t let you customize it. If it says cheese pizza on the menu you can’t add a topping. If it’s a five meat pizza you can’t take ask for only four meats. And there’s only like five pizzas to choose from and I’m married to Mr. Picky…so yeah, just know that going in.

The next morning it was time to head out. We stopped at Mt. Agamenticus and hiked for a few hours. It was so beautiful! From one viewpoint you could see the Atlantic Ocean to your right and snow-capped mountains to your left.

After that we hopped on route 1 and took a leisurely ride towards Boston and Plymouth (we stayed in Plymouth that night) and I’m so glad we did because I found my ideal beach town along the way: York Beach. It was like the perfect little beach town straight out of the 1950s with a soda shop (that we ate at, ’cause duh), an arcade (old fashioned kind of course), and even a bowling alley…all right on the beach. Oh y’all, it was just perfect.

There is one thing we didn’t get to do while in Maine/Massachusetts and that was going on a whale watching trip. We’re already talking about taking the kids back when Lawson gets to be around 4 and that will be the first thing on my list of things to do with them. I think they’d love it.

Here is the Portland cheat sheet (click on this link to get a high resolution copy).

portland cheat sheet

I didn’t mention the shops in this post, but the shops there were great. I especially loved Market Square Jewelers (where I got a pretty new ring (‘new’ meaning from the 1920s of course) that I posted about on Instagram that day) and the Mangy Moose (in Freeport).

Thank you so my friend, Denise, for her awesome suggestions and to my friend, Sarah, as well. This trip was spectacular because of you ladies!

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