Squirrel Island is posh. You don’t realize it until you arrive at the Yacht Club float, and are greeted with, “Welcome to Squirrel Island. Who are you visiting here?” It was a very kind greeting, and I felt welcome, but I also realized that if I didn’t have an answer to her question, I would’ve been told it was a private club. And she didn’t even work as an attendant at the Club!
That said, the Yacht Club maintains several guest moorings, and based on what it says in the cruising guide, visitors are welcome. I’m sure that is true, but I suspect one needs to be very careful when using the amenities. I was thankful I had an answer to the question, and it seemed they were too.
Squirrel Island is one of the first and most exclusive summer resorts in Maine, and likely the United States. It was founded in 1900, and the cottages date back to 1850s and most did not have kitchens, bothrooms or running water until 1930s. The community today feels like it did then since there are still no cars on the island (other than two trucks for deliveries) and only a few golf carts for the older residents. Even cooler, there are no bicyles, scooters or skateboards, so everyone is forced to walk, and therefore interact. The only way to know what year or decade it is it to look at everyone’s gear, vineyard vines, tennis raquets, and baby strollers, phones and tablets. Thankfully my brother had taken away the iPads and iPods prior to the trip.
Tennis is big on the island, and always has been. Squirrel hosted the US Open tennis shampionships in 1920, and has 4 beautiful clay and grass courts in pristine condition. There is also basebell and soccer fields.
My favorite activity is walking or running the path around the island that connects all the houses There is actually a road that can access every house, but they do a good job keeping it hidden. And the path is perfect for a 1.5 mile walk or run, and obviously can be done in laps to increase the doistance.
I’d never been to Boothbay by boat, and it was a nice trip. A solid 5 hours in the Emilie Belle, but that was at 18 knots because I was towing a dinghy. Boothday is far too crowded for me, and I have a feeling if I went by car in the summer, I would make a rule similar to the one I have for Bar Horbor: that I will only go by boat in the high season. But since I had arrived by boat on Squirell, Siobhna and her mother were planning to go to the harbor for dinner, so I joined and we picked up Penn to save him a ferry ticket. It was a good Italian restaurant, certainly better than the less croded harbors, but not better enough to make me want to go back by car!
Squirrel is a gem of an island, and certainly warrants a visit. And if it is made accessible to the public by residents, a huge thank you is in order like the Cruising Guide says.