Discover the Island Charm of Cuttyhunk, MA

Ever wish you could hop in a time machine and go back 50 or 60 years to experience a less frenetic pace of life? It's not as far-fetched as it might sound. There's a place off the coast of Massachusetts where you can do just that ... at least for a weekend.

"It's like 1960 --you're stepping back in time," notes Captain Jono Billings, who owns and operates the Cuttyhunk Ferry out of New Bedford, about 18 miles north of Cuttyhunk Island, a 580-acre arc of stone and sand that's the westernmost of the Elizabeth Islands that lie between Buzzards Bay and Vineyard Sound.

For such a small place, Cuttyhunk has a long, colorful history. In 1602 --nearly 20 years before the Pilgrims landed at Plymouth Rock -- Bartholomew Gosnold sailed from Falmouth, England to establish a colony in the New World, explored the areas near present-day Kennebunkport, Cape Cod and Martha's Vineyard, and built a small fort on what he christened Cuttyhunk Island.

A 70-foot stone tower was constructed in 1902 commemorating the 300th anniversary of that historic landing. After passing through the hands of several English earls and dukes, Peleg Slocum purchased the island in 1693, and her family continued to live on Cuttyhunk for the next 165 years.

In 1865, a group of Rhode Island fishing enthusiasts bought a large portion of the island and built the Cuttyhunk Club and a few fishing stands, enhancing its reputation as a prime spot for sport fishing. In fact, two 73-pound, world-record striped bass have been caught off Cuttyhunk in 1913 and more recently in 1967.

Local fishermen know all the qualities and quirks of the area's waters, offering their services to visiting anglers and acting as expert navigators for ships sailing into New Bedford Harbor, piloting them through the dangerous Sow and Pig Reef on the west end of the island.

Fishing isn't the only way to interact with nature on Cuttyhunk. Half the island is a nature preserve, home to a variety of birds and mammals, as well as wildflowers, sweet peas, bayberry and a host of other flora. Plenty of hiking trails wind through the landscape that's largely craggy and reflects Cuttyhunk's glacial origins. It's covered with the same kind of rocks and stones found in the mountains of New Hampshire and Vermont.

Although largely a day-tripper destination, visitors can overnight on Cuttyhunk with some advance planning. Most boaters prefer to stay aboard their own craft if properly outfitted, but limited accommodations are on land as well. Avalon, the Inn on Cuttyhunk Island, offers seven rooms, while Cuttyhunk Fishing Club has eight. A few cottage and house rentals are also available through Pete's Place Rentals.

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Where to Dock

Cuttyhunk Marina
‍508-990-7578
‍The marina offers 50 transient slips that can accommodate vessels up to 110 feet and have freshwater hookups and 30- and 50-amp electricity capability. About 50 moorings accommodate vessels up to 50 feet. Pump out, ice, picnic area and restrooms are available.

‍Frog Pond Marine Moorings
‍508-992-7530
‍This mooring field is located in the outer harbor off the port side of Bell 6 upon entering Cuttyhunk. Bright white balls mark the moorings, which are first-come, first-serve. Tie up to any mooring that doesn't say PRIVATE, and the mooring collector will come to your boat to collect a $45 rental fee.

‍Jenkins Moorings
‍508-996-9294
‍Located in the outer harbor to the right of the channel's entrance, moorings are first-come, first-serve during the high season. If you spend the night, call and they'll deliver fresh oysters and raw-bar items to your boat.

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Where to Dine

Cuttyhunk Café
‍508-802-8633
‍This coffee shop is located on the town fish dock. Start your day with coffee and pastries, pick up chowder and sandwiches for lunch, and finish the day chowing down on fresh lobster boils with corn, potatoes, onion, chorizo and steamers.

‍Cuttyhunk Fishing Club
‍508-992-5585
‍Just south of town on Cemetery Road, this B&B offers the best breakfasts/brunches on the island, and you don't have to be a guest to enjoy it. They don't take reservations, so grab a cup of coffee and an Adirondack chair while you wait for your table and enjoy the porch with a million-dollar view.

‍Cuttyhunk Island Market
‍508-538-1218
‍Open daily from 9:00 a.m. to 5:00 p.m., this rustic spot offers all the essentials: dry goods, sundries, bread, dairy, fresh veggies, plus 10-inch subs with a bag of chips. We may be small, but we have it all.

‍Cuttyhunk Shellfish Farms
‍508-990-1317
‍This floating raw bar provides fresh Cuttyhunk oysters and clams, along with stuffed quahog and hot clam chowder to boaters during the summer, delivered right to your boat. Call them on VHF Channel 72 or stop in at their shack on the fish dock during the day to place your order.

‍Soprano's Pizza
‍508-992-7530
‍The only sit-down restaurant on Cuttyhunk, this in-season eatery serves gourmet brick oven pizzas and seafood specials. Think a pizza oven held hostage in a garage, four picnic tables in a driveway lit by tiki torches, and a croaking bullfrog in the pond! Can't beat that kind of ambiance.