You’ve heard of the iconic Massachusetts beach vacation destinations: Cape Cod, Nantucket, and Martha’s Vineyard. While all these spots are worth visiting, a lesser-known island off the coast of the Cape is a local hidden gem. Cuttyhunk Island might just be Massachusetts’s best-kept secret.
If you’re after five-star resorts, boutique shopping, and expertly shaken martinis, you’re probably in the wrong place. While I enjoy indulgent trips as much as the next girl, there’s something special about the laid-back and unpretentious atmosphere of Cuttyhunk.
Cuttyhunk Island is the outermost of the Elizabeth Islands, located off the coast of Massachusetts. The island is relatively small, just a mile and a half long and three-quarters of a mile wide. Trust me when I say that what the island lacks in geographical size is made up for in terms of character and charm. Cuttyhunk has quickly become one of my favorite places, luring me back summer after summer.
Transportation to and on Cuttyhunk
To get to Cuttyhunk from mainland, there is a ferry service from New Bedford, MA. Private boat owners can also arrive by boat and dock in Cuttyhunk’s marina.
Something worth noting – there are very few vehicles on the island (most of which are owned by year-round residents). In our time there every summer, we travel around on foot, by bike, or by golf cart. While booking accommodations, inquire about reserving a golf cart if that interests you. Bikes are also a valuable mode of transportation; however, you’ll need to bring your bike on the ferry. Boat, bike, kayak, etc. rentals are unavailable on the island.
Part of Cuttyhunk’s charm is the lack of automobiles. Golf carts and bikes are constantly buzzing around the island, and there isn’t a traffic light to be found. Beach traffic is also non-existent in Cuttyhunk – a distinguishing feature compared to the other high-traffic islands in the area.
Where to Stay on Cuttyhunk
Avalon Inn
Since the island is quaint and lesser known, accommodations can be a bit challenging to come by. There aren’t any hotels on Cuttyhunk, although there are a few inns and bed-and-breakfasts. Every year, we visit with a larger group of 20 to 30 people and book the Avalon Inn for the week. The Avalon is an older building that is well-kept and perfect for larger groups. It sits atop a hill and has gorgeous views overlooking the ocean.
Cuttyhunk Fishing Club B&B
Another popular option is the Cuttyhunk Fishing Club. The B&B has eight rooms and serves breakfast daily. While I haven’t stayed there myself, family members have and mentioned it’s a great option. Vrbo & Air BnB rentals are available on the island as well!
Things to Do on Cuttyhunk
Churches & Barges Beach
The majority of our days on Cuttyhunk are spent lounging on the beach. The two most popular are Churches Beach (my personal favorite) and Barges Beach. Both options are beautiful and, most notably, not crowded. Growing up in the Northeast, I can attest to how packed beaches are during the peak summer season. It’s so refreshing to sleep in and leisurely make your way down to the coastline without worrying about finding space for a larger group.
Fresh Oysters & Stuffies at the Main Dock
After a long day at the beach, venture down to the dock and order fresh oysters, ‘stuffies,’ and clam chowder at Shellfish Farms’ Raw Bar. Oysters are caught and shucked on the dock daily! There’s also an ice cream stand, lobster stand, and small cafe with coffee and treats by the pier. A little something for everyone.
Grab Merch at the Corner Store
Once you’ve had your fill of seafood, swing by the Cuttyhunk Corner Store for a little souvenir shopping. I make it a tradition to grab a new long-sleeved shirt every year – they’re my go-to for cozy days at home.
Hit the Trails
The west side of Cuttyhunk is a nature preserve with trails for walking and biking. We’ve gone for walks here on overcast days to explore the off-the-beaten-path beaches in the area. The paths tend to be buggy, so bring bug spray!
Things to Know About Cuttyhunk
Cuttyhunk is a Dry Island
A small market on the island carries the necessities, although I recommend bringing groceries over since it can be slim pickings. Cuttyhunk is also a dry island, meaning no alcohol can be served or purchased there. We usually do a large grocery and liquor store run beforehand to ensure we’re stocked on everything we’ll want and need during our stay.
The Dock Jumping Tradition
Depending on the day, there are one or two ferry departures from Cuttyhunk. The real event isn’t the schedule, it’s what happens after the boat pulls away. As the ferry departs, locals and visitors alike gather at the dock to leap into the harbor waters. The tradition is a spirited send-off, rite of passage, and a little slice of what makes Cuttyhunk so special.
Whether you’re saying goodbye for the season or just cheering from the dock, the pier jump exemplifies Cuttyhunk – simple, joyful, and best experienced at least once. Trust me, you’ll never forget it.
All in all, Cuttyhunk is a special place. Everyone on the island is kind, respectful, and friendly. The days are long, the nights are cool, and the stargazing is mesmerizing. Life tends to slow down on the island; it feels like you’ve been transported back in time. It’s hard to articulate the magic that is Cuttyhunk in words… you’ll have to experience it firsthand for yourself.
Until next year, Cuttyhunk.