It took about 4 hours to get to Cuttyhunk and then another 45 minutes to go around the island to enter its very protected harbor. There were not too many boats there, but it had an extensive mooring field. We tied up to one of the mooring balls, the eyelet variety, which is a bit trickier, but all went well.
Cuttyhunk is part of the Elizabeth group of islands that are located just north of Martha’s Vineyard. Most of them are privately owned by the Forbes family. Cuttyhunk was the first English settlement in New England but only lasted 22 days! The Cuttyhunk Fishing Club bought most of the island in 1863 and its members included Jay Gould and others like him. Their guests included Theodore Roosevelt, Grover Cleveland and William Taft. Now the island is sparsely populated with only 52 full time residents. It attracts boaters and fisherman to its lovely harbor. There are very few tourist accommodations - a couple of inns on the island, and a few homes available to rent scattered over an area 2.5 by 1.5 miles.
That night Jonny went for a paddle while Lynn prepared meatloaf for dinner. All of a sudden a boat pulled up with two young women selling raw oysters, clams and shrimp cocktail! So that took care of the appetizer course of our dinner - delicious shrimp cocktail.
On Wednesday, we packed a picnic lunch and took the dinghy in and tied up at the town dock. The townspeople we met were very warm and friendly and very careful about Covid (as is almost everywhere we’ve been in New England). No wonder they are doing so well in their recovery!
Our plan was to spend the day hiking around the island. There are lots of trails that line the waterfront and roam through the woods. We took one trail up to the highest point of the island and had an incredible panoramic view.
Some of the trails took us up cliffs where we could see across to Gay Head, the sandy cliffs of Martha’s Vineyard. Most of the “roads” were really just dirt paths and the only paved roads were in the tiny village area near the harbor. The only vehicles we saw were a few golf carts and one pickup truck.
Scattered throughout the island are bunkers that were used during World War II by the U.S. Army. Two hundred fifty soldiers were stationed on Cuttyhunk to watch for German submarines!
The village center included lovely natural shingled homes and an inn with amazing stonework.
A small market was only open to on-line orders while we were there. The restaurant (in the owner’s yard), a small museum, the town hall and the school were all closed. But at the town dock one can get a take-out breakfast and order lobster dinners to go, which of course we did! That evening, the raw seafood boat came by again but we were clearly satiated with our lobster. We are definitely taking advantage of our favorite New England seafood on this trip!
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