Windjammer Festival | Boothbay Harbor, ME

Everyone has their own coastal town of Maine. Mine happens to be Thomaston and Rockland, but my boyfriend’s is Boothbay. They’re all basically the same thing. Some have more things to do than others, but — when it comes down to it — shopping, food, salt water, and boats are what each community revolves around.

The last full of week of June is the Windjammer Festival in Boothbay, and I’m happy to adopt Boothbay as my coastal Maine community for just that week each year. The Festival is the start of tourist season for the town. All the shops are open and stocked full of knick-knacks, handcrafted goods, and expensive jewelry. Although the festival was supposed to be a week this year, it’s really a two-day ordeal. On the Tuesday of the week is when everything starts — the raffle, the Antique Boat Parade, and the hoards of bourgeois vacationists.

Here’s the best kept secret from spying tourists, though. The Used Book Store on top of the hill is the crowning jewel of my trip every year. Most books are 50¢, but they go up to as high as $3. All the books are delivered from the library, and this is the one time each year where they do the sale. Between my boyfriend and I, the classics section of the store is wiped out within 10 minutes of the store opening. At this point, we really need to create our own library. However, when we build our house in a few years, our only definite plan is to have a whole level become a custom library filled with our books. It will look similar to the Beauty and the Beast library.

Also be sure to thoroughly browse through Enchantments. It’s a hippie-esque store where each shelf is stuffed with odd finds. I was able to purchase a beautiful surrealist photograph this year that I’m absolutely in love with. It’s called O Duomo Mio by Thomas Barbey. You’ll find vintage posters, boho garb, glass, books of zen, wicca, and others, wind chimes, jewelry, and anything else you could imagine.

On Wednesday, is the Windjammer Day. In the afternoon, all the Windjammers and Schooners sail into the harbor where they anchor for the night. Usually four or five boats sail in, taking up the majority of the harbor. This year, only two came. It was rather disappointing, and I can only presume that it’s due to the change in festival management this year. Hopefully, it will be back to normal next year.


Other than that, though, very little happens. So be prepared to eat, drink, sunbathe, drink, shop, and, oh, did I mention drink? It’s a vacation in the true sense of the word. Nothing but sea breeze, sun, alcohol, and good food.

Speaking of good food. The absolute best restaurant in the whole of the harbor is The Thistle Inn. If you don’t eat there, you’re crazy. Both their pub menu and their fine dining menu are fantastic! Specifically this season, the pan seared scallops on a spinach and couscous risotto were fantastic. A choice like that on a menu is a gamble because risotto — even at the best restaurants in the world — are incredibly hard to make well and are even more hit or miss. However, The Thistle Inn hit it out of the park. It was by far the best choice on the fine dining menu. However, everything was great — the Lazy Lobster, the Lobster Paella, the chicken, the steak, the oysters, the crab cakes, everything.

So, if you find yourself in the Boothbay region for Windjammer, look up at the corner balconies of the hotels and you’ll find myself, my boyfriend, and the in-laws each and every year. Remember, though, this is not a trip to take if you’re looking for a travel adventure. This is the epitome of a vacation.


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