Maine has always seemed somewhat exotic to me, probably because I’m from Hawaii, the farthest state from Maine as possible. I’ve always had a desire to visit, fantasizing about steaming lobster in a quaint cabin we rented on the coast. Anthony and I even made friends with a couple from Maine on our Morocco trip back in 2017, and though they invited us to their riverside cabin in Edgecomb, we never made it up there. Maine always seemed just a little too far — if I was going to spend eight hours traveling, I might as well go to Europe, right? It wasn’t until COVID, when I was desperate for another road trip, that a friend informed me that a delightful beach town called Ogunquit is only five hours away from New York City. FIVE HOURS?! Our previous trip to the Finger Lakes took that long! I dove into research and could sense almost immediately that I would love it here. In fact, less than two weeks after our first trip to Ogunquit, we returned because we had so fallen hard for it. Here are some of my recommendations:


I honestly don’t know if we would have loved Ogunquit as much if we hadn’t stayed at 2 Village Square Inn. This impressive, three-story bed & breakfast overlooking the rest of town is easily the best b&b I’ve been to in the U.S. The owner, Bruce, was the epitome of a host, making each guest feel like part of a family. There are 17 charming guest rooms, and I was impressed by the detailed description of each room on the website. Both of the rooms on our two separate trips had direct views of the water, and I loved waking up to the sunrise — the first light to hit (continental) America! The rest of the b&b is just as lovely, from the heated saltwater pool and jacuzzi, to the porch with rocking chairs. Each morning, we found a different spot on the three-acre property and were given a laminated menu and dry-erase marker to make our breakfast selection. The food was as wonderful as I expected: French toast with berries on one day, scrambled eggs and hash browns with peppers another day. Bruce checked on each guest to ask if they wanted a refill on anything. Freshly-baked blueberry scones and cookies were individually wrapped and available throughout the day, as was local coffee in the lobby. I could go on and on about how exceptional 2 Village Square Inn is, but just take my word for it: Book this place and book early because it sells out quickly and is full of return guests who also know what a dream this place is. 


The first thing you should do in Ogunquit is walk along Marginal Way. This 1-¼ mile winding cliff walk connected our b&b to Perkins Cove and is the most scenic way to get across town. There are 39 socially distanced benches scattered along the walk, and we appreciated the unending opportunities to climb down rocks to get closer to the sea.

Anyone visiting Maine for the first time should take a lobstering boat ride, so that’s exactly what we did. We sailed with a lobsterman and an extremely knowledgeable tour guide (as well as a few families with young children), stopping by various traps to haul in freshly caught lobsters. Lobsters are fascinating! We learned that “lobsters never die.” Basically, lobsters don’t age, they do not grow weaker, and they do not become infertile. In fact, they become more fertile in their old age. Lobsters can regenerate lost limbs and regularly outgrow their shells. Once their waistline feels a little snug, a lobster will shed its shell, pump itself full of water to grow, then harden its outside into a new shell. (This is where soft-shell lobsters come from; they’re lobsters caught during this molting period.) Lobsters that have just molted are at a vulnerable stage for about three months until their new shell grows. Since lobsters don’t have bones, they can shed and grow indefinitely. Maine has strict laws about what type of lobsters can be harvested; they must be a certain size, and cannot be pregnant. When our lobsterman hauled in a pregnant one, he threw it back out into the sea. Female lobsters carry thousands of eggs, so pregnant lobsters are much more valuable in the wild than on a dinner plate. To book a trip, just call FinestKind as soon as possible. They have multiple trips throughout the day, and other trips besides lobstering ones, but they were selling out quickly when we were there.

I wasn’t too eager about checking out the beaches in Maine (I’m from Hawaii, after all!), but when we first went to Footbridge Beach around dusk, I was in awe. After crossing a little wooden bridge over idyllic marshland that gave me flashbacks of Normandy, we arrived at the most expansive beach I’ve ever seen. With soft sand that reminded me of Lanikai, this wide, flat beach with a low shore is the perfect place for young children learning how to swim. It’s also much less crowded than other beaches in Ogunquit, and it was so tranquil walking along the water. We visited a second time in the late morning, and it was decidedly less romantic and filled with more families, but it’s so spacious that even then it was hard not to appreciate the beach. It’s best to either walk or catch the trolley to Footbridge Beach, as the nearby parking lot charges $25 for the whole day. If you get there early and leave before 8am, or come late, I think they stop charging for parking.


Obviously, we had to eat lobster at every meal. It was my first time in Maine! Our favorite lobster happened to be the first place we tried, and it also happened to be the cheapest. We ate at The Lobster Shack twice during their lunch special: $20 for two one-pound lobsters, corn on the cob, and coleslaw. Yes, you read that right: $20 for two really good lobsters. I have yet to see a better deal anywhere else. The casual restaurant is housed in a former shack that once stored traps, rope, buoys, and other fishing equipment for lobstermen.

Our b&b gave us a $100 gift certificate (see, aren’t they perfect?) to Ogunquit Lobster Pound, so we had two dinners there. On our first night, we went on a Saturday around 7pm. Big mistake. The restaurant comprises both an indoor space that resembles a gigantic log cabin and a vast outdoor area that reminded me of camp. But the size of the space didn’t matter; it seemed like all of Ogunquit was here for dinner. We ended up waiting an hour and a half to be seated. For the second dinner, we learned our lesson and arrived earlier (and on a Sunday) and were seated immediately. To order, we walked up to the tank and chose which lobster we wanted, then they cooked it and brought it out to our table. It was a fun experience and a great way to enjoy lobster. Random tip: Their free bread is phenomenal!

Another lobster spot we tried was Barnacle Billy’s, which seems to be on everyone’s must-trys. I preferred The Lobster Shack for its lunch deal, but this restaurant was more atmospheric because you can eat right on the water.

If, for some reason, you’re sick of lobster, Brix+Brine is a chic raw bar. Don’t forget that Maine is also amazing at oysters!

Quick Day Trips

About a half-hour drive north is Kennebunkport, the fancier version of Ogunquit. It’s where the Bush compound is, if you’re into that. We had some extra time so we drove up to have lunch at the famous Clam Shack. There was a long line, but the lobster rolls were worth it! Cheap parking is available in the lot behind The Clam Shack. Also check out Rococo for ice cream flavors like chai cardamom, goat cheese, and guava and Maria cookies.

A 15-minute drive south is Cape Neddick, a gorgeous little peninsula that houses the iconic Nubble Lighthouse. If we had more time in southern Maine, I probably would have wanted to spend a night on Cape Neddick!