Sailing Mystic Hearts

Cuttyhunk Island is part of the Elizabethan Islands just northwest of Martha’s Vineyard in New England. As the far western island in the chain, it lies between Buzzards Bay and Vineyard Sound. Easily a day sail from nearby Block Island, Newport, or Nantucket (where we cruised from), it’s well worth a visit for the beauty and tranquility that the small little island offers. If you choose to spend more than a few days here, note that provisions, restaurants, and shopping is limited on the island. There is one market just up the main road from the dinghy dock that operates on limited hours. A seafood boat makes deliveries to boats in the anchorage, but we didn’t purchase any. I’ve also read that there is now a cheese shop in town that sells charcuterie boards, but it wasn’t in existence last summer while we were there. 

Fun note about wildlife: Coyotes were one of the last animals we would have expected to see at Cuttyhunk. Over the years, coyotes made the swim from Cape Cod to each island down the Elizabethan Island chain, finally ending up at Cuttyhunk, but that’s exactly what they did. While dinghying into town on our last visit there, we saw a funny-looking gray ‘dog’ with a long snout sitting at the end of the beach next to the channel. It didn’t seem afraid of our presence as we passed by at a distance, so I took a photo, zoomed in, and realized it wasn’t a dog at all. Such a beautiful creature, and living in one of the prettiest places we’ve ever visited.

FAVORITE ACTIVITIES

BARGES BEACH – This is a lovely little beach! Accessible by the entrance to the harbor, there are places you can pull your dinghy up ashore. We preferred to use the dinghy dock in town and walk to the beach, but either should be fine. Just take note of any signs marked on sections of the beach where beaching a vessel is not allowed.

LOOKOUT PARK – Take Tower Road up to Lookout Park, the highest point on the island, for 360 degree views of water. The walk itself isn’t too strenuous for being uphill. On a clear day, you can see Martha’s Vineyard to the southeast. The view from the top was the closest we’ve felt to being back in the British Virgin Islands where you can see all the islands in the distance (minus the palm trees, of course). There are some old WWII bunkers at the park. We have not personally wandered on any of the trails into the scrub. New England is tick country (with Lyme disease being a very real threat), so cover up, wear appropriate bug spray (especially around the ankles), and check yourself very well after adventuring outside. Ticks in New England are awfully tiny and easy to miss. Checking oneself by touch (especially in warm spots like the back of the knees and groin area) and then having a partner visually check works well.

WALK TO COPICUT NECK – One of the more beautiful walks on the island will take you down Bayview Drive past the Cuttyhunk Yacht Club (less of a yacht club and more of a place where the kids pick up their Sunfish sailboats) and down Blue Heron Drive. Again, wear bug spray (we found mosquitoes out here after a little while), but the views of Cuttyhunk Pond and the tiny Cape Cod style homes on the hills were beautiful. The whole area looks like the photos you see on postcards.

ACTIVITIES ON THE LIST FOR NEXT TIME

CUTTYHUNK HISTORICAL SOCIETY – From our understanding, the historical society is a small museum with a few exhibits and local artifacts from the island’s history. Originally settled by Native Americans (the Wampanoag tribe) and later the English, there is much to learn about the early history of the island and how Cuttyhunk made a name for itself.

RESTAURANTS

CUTTYHUNK CAFE – We had breakfast here one morning and sat on the dock. We were not impressed with the quality of the food, so we won’t be returning.

CUTTYHUNK LOBSTER SHACK – We didn’t actually eat here and can’t attest to the food quality, but this shack on the waterfront was a bit pricey for our liking (pricier than Nantucket, where we just sailed from, so that’s saying something). Last summer, lobster dinners were $52, hot buttered lobster rolls were $44, a whole lobster (no sides) was $42, and orders of french fries were $10. They had several other food items to choose from, but we opted for our own homemade seafood dinner on the boat.

SOPRANO’S – With limited food options on the island, this place is our favorite! It’s a pizza place run out of a family’s basement/garage, with picnic seating available in the driveway. It’s usually busy during the summer months when they are open; we took our pie back to the boat to enjoy.

SHOPPING

CUTTYHUNK CORNER STORE – Located at the corner of Broadway and Bayview Drive. You can’t miss it; it’s at the first intersection as you walk away from the dinghy dock. If you like to collect souvenirs, or want a t-shirt with the name “Cuttyhunk” on it, this is the place for you. I believe this store is open seasonally, so best to check the hours before visiting.

HELPFUL INFO FOR BOATERS

TRASH – There are no public dumpsters available.

RESTROOMS/SHOWER FACILITIES/LAUNDRY – There are public toilets at the waterfront, but no showers or laundry facilities.

MOORINGS – I believe moorings in the outer harbor were $55/night when we visited in 2021. (Our boat is too large for any of the moorings in the inner harbor, so we didn’t attempt to go in the channel.) There is plenty of space to anchor outside the outer mooring field, so this is what we recently did. 

GROCERY – Cuttyhunk Island Market has limited provisions and operating hours. We’ve never had a need to shop here, but hear they carry the essentials.

We love Cuttyhunk Island and know that we will always look forward to sailing here when in New England. It’s the perfect island for a small getaway, to enjoy long walks in nature, or even an afternoon on the little beach.