Hey, hi!

Have I told you lately… that I love Maine? It’s the perfect blend of coast and woods, northeast no nonsense ‘tudes and friendly vibes, cities and towns with food scenes and remote, off-grid areas. It feels separate from the distinctly preppy part of New England that is Nantucket, and is more Patagonia vest for utility as opposed to finance, you know?

There’s so much of Maine left to explore, but I have to say, we had a pretty perfect long weekend on the midcoast. We stayed on Westport island, which was sliiiightly inconvenient, but worth it because the inn we stayed at was so charming and secluded. It was about a 45 min drive south to Freeport, and about 15 mins more to Portland. Next time we visit Maine I really want to see Acadia national park, so I suppose we’ll just have to make this an annual tradition. Here’s what we did:

Friday

Stay at the Squire Tarbox Inn

Quaintness friggin’ abounds at this little inn — I can’t say enough good things about it. I ended up picking it because it was like, $500 for three nights on 4th of July weekend, so it felt almost too good to be true. Guess what? It was true, and then some. When I booked, almost all the rooms were available, but it was full of people come the weekend.

It’s a historic property with the first structure dating back to 1760, and it’s been truly lovingly restored (not just in terms of marketing BnB speak) and decorated. This is the kind of place I would kill to live in — so I very much soaked it up while we were there.

Our stay included breakfast, and if you ask me what my perfect breakfast is, it’s what we got. Yogurt, granola, fresh fruit, a baked good, and an egg dish every morning prepared by a sweet little lady named Olga. We didn’t bring Oswald because we wanted to do some activities that he’d be too lazy for or not allowed at, but this is a dog friendly place and there were a handful of doggies there that made us miss our own little idiot.

Breakfast in Boothbay Harbor

I actually think Boothbay Harbor was the cutest town we stopped in throughout the trip, and it was also the first. We got breakfast at Waves, an adorable little diner that had a surprisingly quick wait time during peak breakfast hours, then did a lap to some of the shops and by the water. I got some salt water taffy I was excited to eat before realizing that half the bag was licorice flavor (yuck) and picked up a new hat because I was in need of a performance fabric one that I can get wet in the pool.

On our way to the next thing, we also stopped at an adorable craft fair where kids were literally doing burlap sack races and the local rotary club was selling lemonade. I bought a little bud vase from a lovely ceramics lady and we got suckered into a passionfruit maple syrup concoction from a cute old dude we couldn’t pass by.

A Little Nature Walkabout

I was craving outdoor time but I’m not much of a hiker, I’m more of a… walker. I found this 1.7 mile trail near the inn that was a mix of woods and water, but some of the water appeared to be dried up? Sad. We still enjoyed our little jaunt, though, and I looked so cute in my new hat (which happens to match our latest water bottle addition)! A win is a win.

Lobster Rolls for Lunch

Here’s where we made a wrong turn. I wanted to hit Five Islands Lobster Co., but it was out of the way from the inn, so instead we stopped in Wiscasset, which is much closer. There’s two lobster shacks right across from each other there: Red’s Eats and Sprague’s Lobster. Red’s had a big line we didn’t feel like waiting on, but it turns out, all those people were onto something. I can’t speak to the quality of Red’s, but I can tell you that Sprague’s lobster roll was not worth $35 (lots of meat but rubbery and lacking in flavor), and their fish and chips was one of the worst I’ve had, and I’m a get-fish-and-chips-everywhere-I-go kinda gal. Next time, we’ll go to Red’s or Five Islands.

Some Antiquing Never Hurt No One

You didn’t think I’d go somewhere for the weekend and not hit an antique store, did you? Every time we pass an antique or thrift store, a sign that says “yard sale” or “estate sale,” or just a sorry looking piece of furniture on the side of the road, Jeffery looks at me out of the corner of his eye to see if I’ve noticed, waiting for me to screech at him to pull over.

Well guess what? We pulled over for this one. It just happened to be closing within the half hour when we arrived (saved by the bell, Jeffery), so we didn’t linger too long. There were stacks of vintage postcards I wanted to get for wedding thank you cards, but a sudden sickness from the fish and chips came over me, and the lights actually went off while I was in the bathroom :). So I scurried out empty handed and we headed back.

An Afternoon Nap, Then Dinner and Ice Cream

There’s not much better than a shower and a little nap before dinner on vacation, and this was no exception. We laid around a bit in our room then moseyed out back to lay on the grass and listen to the froggies before dinner. (I finished Wuthering Heights btw, it ruled.) We ate at Montsweag Farm Restaurant which was perfectly nice and full of sweet local families and older couples, and booked it over to Witch Spring Hill ice cream before they closed for soft serve. Idk why, but this soft serve was some of the best I’ve ever had? The vanilla and chocolate were both so perfectly balanced, and I’ve been chasing this high with lesser versions since. I’m not kidding when I say I think I’ve had like five soft serve cones in the past two weeks. It’s becoming a problem.

Saturday

Montsweag Flea Market

After breakfast at the inn, we got on the road to Portland, and naturally had to stop at the little flea market I saw the day prior. My grandpa had a permanent stall at a flea market when I was a kid, and while digging through old stuff always reminds me of him, flea markets in particular make me feel close to my fave guy. I didn’t end up buying anything, though, because I’ve become more discerning after years of pawing through vintage wares — it’s gotta really be something special these days to come home with me.

Shopping and Eventide Oyster Co. in Portland

I was pumped to spend the day in Portland because I loved it the first time I went some 7 years ago, but after spending time in smaller towns the day before, I was sort of itching to get back to a more rural area? My one non negotiable for Portland, though, was to get the lobster roll at Eventide Oyster Co., which I’ve been thinking about since I ate it last. It’s different from typical lobster rolls in all the best ways with brown butter, tender meat, and a pillowy bao bun. We also got donuts at the Holy Donut and we… fully do not understand the hype, lol. They were dense and claggy and stale? Maybe that’s what potato donuts are supposed to taste like, but I’m all set!

A Little Boat Tour of the Bay

I was tip tapping around the internet to find some fun excursion for us to do and settled on this boat tour of Casco Bay, which I recommend. It passes by several lighthouses, forts, and other landmarks, and the guy who did the narration of the trip was really sweet and enthusiastic. Oh, we also saw some seals! I did fall asleep for about 15 minutes, but that’s because I took an original formula Dramamine, okay?

The L.L. Bean Flagship Store in Freeport

I’d be lying if I told you that half my motivation for going to Maine wasn’t to go to the L.L. Bean store. We spent at least two hours there on the way back to the inn from Portland, and another good hour or so on the way home on Sunday, because I had to pick up my monogrammed Boat and Tote (a Wirecutter pick, TYVM). I was so overwhelmed by my urge to buy everything I saw, but settled on a large beige-on-beige with long handles and a zippered top, plus a big “C” monogram in maroon. I’ve since added a mini Boat and Tote keychain and another charm I made out of fishing lures and flies I found in the hunting and fishing store, of course.

Sunday

Last Bits in Wiscasset

Since we didn’t spend any real time in the downtown area of Wiscasset, we stopped off here on the way home and I’m so glad we did. I got a signed copy of Katie Sturino’s new book for my friend Maura from the bookstore Fiction, a really great iced matcha latte and turkey wrap from Treats, and I wanted to buy every last piece of stationery from Rock, Paper, Scissors. I wanted to check out Widener Co. that I’ve seen on TikTok, but they didn’t open till noon and we had — what turned out to be — an eight hour drive ahead of us.

That’s all for now! I still owe you the everything-we-bought-and-made wedding issue — don’t think I forgot. I’m just a little pooped from life and all the writing I do during my day job, yanno? Anyway, love you!