Falling for Cuttyhunk

For many boaters, the quiet days of autumn are the very best time to visit this peaceful, scenic island off Southeastern Massachusetts.

By Gaelen P. Adam | Photography by Tom Richardson
Autumn can bring lakelike conditions to Cuttyhunk’s inner harbor.

All of the things that make Cuttyhunk such a great summer destination—long, sandy beaches, narrow roads, cute shops, protected anchorages and fish-filled waters—apply in the fall, too. But after Labor Day, the character of this isolated outpost at the end of the Elizabeth Islands changes, becoming quieter, more relaxed and—impossibly—more beautiful.

While the island’s inner and outer harbors are unlikely to be empty on the weekends in September and even October, they are much less crowded. Better still, the water is warm enough for swimming, especially in the inner harbor, but you’ll want a sweatshirt when you get out. The evenings can be downright chilly—perfect for snuggling in a sleeping bag rather than baking in a stuffy cabin during the dog days of summer. As the days get shorter and cooler, the sea breeze begins to slacken as well, which makes for a more comfortable ride to and from the island and better conditions for kayaking and fishing.

Boaters often have their choice of moorings during the shoulder seasons.

Island Exploration

Fall is also a wonderful time to hike the myriad trails and dirt roads that wind through the nature preserve on Cuttyhunk’s southwestern side. The weather is cooler, the tall grasses and wind-stunted bushes and trees that line the hillsides are turning golden brown and red, and the low humidity makes for spectacular views.

If you follow the trails to the southwest corner, you’ll find a tower that was erected in 1902 in commemoration of the 300th anniversary of Gosnold’s discovery of the island, sitting in the middle of Western Pond. Along the way, you’ll pass several of the six former World War II lookouts, including one that now serves as a viewing platform atop the 154-foot-high Lookout Hill.

Walk back along the dirt road that skirts the southern side of the island and you’ll be treated to views of Aquinnnah on Martha’s Vineyard and the vast Atlantic beyond. Eventually, you’ll pass the historic Cuttyhunk Fishing Club, built in 1864 for wealthy sport fishermen from New York and now a cozy a bed-and-breakfast inn.

Sites & Shops

On the road leading up the hill above town is a one-room schoolhouse, built in 1873 and home to a playground. Nearby, you’ll also find the island library and the headquarters of the Cuttyhunk Historical Society, whose exhibits range from Coast Guard rescues and storm stories to the island’s role in World War II and its history as a world-famous fishing destination.

If there’s one drawback to visiting Cuttyhunk in the fall, it’s that the few shops and local market are only open for short periods, if at all. It’s worth noting the open hours when you visit, however, as the shops often feature unique local crafts, plus you’ll get a better sense of what the island is all about outside the busy summer season. Just be sure to bring cash, as many places don’t take credit cards.

Heading for the Harbor

No matter what time of year you visit, getting to Cuttyhunk from the Buzzards Bay side is straightforward, even at night, so long as you pick up the unlit buoys that mark each of the two wide channels that lead to the outer basin. If approaching from Vineyard Sound, note that the route through Canapitsit Channel is narrow and fairly hairy, especially in a southwesterly or offshore swell; for newbies, the best and safest approach from the Sound side is to enter Buzzards Bay via Quicks Hole and proceed from there.

The jetty-lined cut into the more protected inner harbor is narrow, but deep, and there is plenty of water throughout the mooring field—up to 10 feet. You can pick up any mooring not marked as private, and the harbormaster will come by to collect the $45 mooring fee. Note that the Cuttyhunk moorings only accommodate boats up to 50 feet, and although rafting is allowed, each boat will be charged the whole $45. You can also take advantage of the anchorages and save the mooring fee.

The channel to Cuttyhunk’s inner harbor is deep and well-marked.

Island Amenities

If you’d rather get a transient slip, the town-owned Cuttyhunk Marina has them, as well as ice and a dinghy dock. The marina docks are home to shops selling fresh seafood and ice cream. There are also restrooms on the dock (but no showers), and often a lunch cart, but the island is dry, so be sure to bring your own alcohol if you want it. You can also beach a dinghy near the former Coast Guard Station for a walk on Barges Beach, or to swim and watch the boats pass through the cut. However, be aware that both the ferry and the water taxi dock at the Coast Guard station, so leave the approach clear for them.

Cuttyhunk’s inner harbor is protected in all directions, and is very quiet during the off-season. However, if you’re looking for a night ashore, make a reservation at the Cuttyhunk Fishing Club Bed & Breakfast Inn. Even if you sleep aboard, you’ll want to enjoy breakfast on the Club’s verandah, which overlooks Vineyard Sound. The Cuttyhunk Ferry services the island only once or twice a week during the shoulder seasons, steaming from New Bedford in the morning and returning in the afternoon. While docked on Cuttyhunk, the ferry offers light food and espresso all day.

Combining minimal attractions with a host of outdoor experiences, Cuttyhunk is a great option for a late-season cruise or daytrip. Newport, Block Island, Martha’s Vineyard and Cape Cod are all within easy reach of Cuttyhunk, and are at their most beautiful in the fall, not to mention far less crowded and less expensive—all good reasons to extend your boating season through October.

Cuttyhunk Names & Numbers


(508) 990-7578; VHF 9

Dockage, Moorings & Service

Cuttyhunk Marina (508) 990-7578
Public marina with transient slips, moorings and fuel. Slips have water and electric.

Jenkins Moorings (508) 996-9294
Rents transient moorings in the inner and outer harbor.

Frog Pond Marine (508) 992-7530
Manages transient moorings in the outer harbor only.

A public anchorage is located in the northeast corner of Cuttyhunk Pond. A second anchorage can be found in the outer harbor, just west of Canapitsit Channel.

Cool Shops

Cuttyhunk Market
Carries basic provisions at the corner of Broadway and Post Office; hours are limited in fall.
Cuttyhunk Fish Market
Fresh fish and shellfish on the town dock.
Cuttyhunk Corner Store (508) 984-7167): Clothing, gifts and more a few steps from the harbor.
Sea Girl Gifts (508) 990-9820): Handmade bags, jewelry, clothing, funky ornaments, hats and more.

Where to Eat

Cuttyhunk Fishing Club B&B Inn (508) 992-5585
Serves breakfast to guests and non-guests alike on the veranda overlooking Vineyard Sound.
Cuttyhunk Shellfish Farms (508) 971-1120
Floating raw bar that delivers direct to your boat. Also offers lobster bake and raw bar catering.
Bart’s Cart
An institution at the town docks; serves breakfast and lunch items in season, weather permitting.

Things to See & Do

Cuttyhunk Historical Society, Museum of the Elizabeth Islands (508) 984-4611)
Home to exhibits on island history and ecology, as well as trail maps. Open late June to Labor Day.

Fishing Mecca

Cuttyhunk has long been famous for producing big bass.

Cuttyhunk has been regarded as something of a holy land among striped bass fishermen since the mid-1800s. That’s when a group of wealthy sportsmen—defectors from the nearby West Island Fishing Club off Little Compton, Rhode Island—established an elite bass-fishing club on the southern shore. Perched on spindly stands extending from shore, the anglers would cast lobster tails into the surf for huge bass and bluefish. The island’s reputation as a striper mecca was further cemented in 1913, when local angler Charlie Church pulled the then-world-record fish of 73 pounds from Canapitsit Channel.

Today, the rocky inshore waters surrounding Cuttyhunk continue to harbor large stripers throughout the season, which typically extends through October. Indeed, fall can be the very best time to fish the island, as it serves as a holding area for bass that are fattening up for their southerly migration.

If new to the area, hiring a guide for a day or half-day trip is money well spent, and Cuttyhunk is home to some legendary guides, including Bruce Borges, Jimmy Nunes and George Isabel. Many of these local skippers fish the famous Sow and Pigs Reef southwest of the island, which takes plenty of local knowledge to fish well (and safely). Of course, you can also do well by simply casting plugs and eels along the same beaches fished by our angling forbears—and you don’t even need to use lobster tails for bait! — Tom Richardson


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