October is prime-time for a fall surfcasting trip to the hallowed striper grounds of Cuttyhunk Island
Growing up as a surfcaster, I have read many epic tales from the fabled striper waters of Cuttyhunk, yet for some reason at 24 years old, I had yet to take the plunge and experience it for myself. The stories are almost mythical, and like many legendary fishing grounds, often times reality fails to live up to the imagined. My first trip to Cuttyhunk was not one of those instances— it lived up to expectations.
I’m sure our report pales in comparison to some of the striper action that takes place every year at Cuttyhunk, but the manner in which our first trip to the island unfolded was special and an experience I will never forget.
Four of my closest friends and I, all mid-20 year olds who’ve recently been bit by the surfcasting bug, set our sights on the weekend of October 17th for a prime-time fall fishing trip to hallowed striper grounds. Like true novices, we boarded the Saturday morning Cuttyhunk ferry from New Bedford with way too much fishing tackle, not enough sleeping bags (I forgot mine), and a palpable nervous energy that dripped both excitement and concern that our expectations would fall flat.
The ferry was quiet and nearly empty; aside from a few old-timers and their dogs, it was just us and another crew of three surfcasters. I was glad there were other fishermen on board. They were older than us and visibly brimmed with excitement—they’d probably done this before, I thought.
In an hour’s time we arrived at the island and were greeted by a few locals who had plenty to say about the subpar fishing of recent weeks. “Lots of small bass around”, they muttered. The other group of surfcasters, who were armed with a far lighter load of equipment, were not fazed. They reassured us that this weekend would be prime fall fishing. The child-like looks in their eyes instilled confidence in us Cuttyhunk virgins, and we trekked off from the dock convinced that the report of smaller bass was a precursor to the arrival of some hogs.
We lugged our cumbersome load of equipment through what seemed like a ghost town and took the first trail we saw that pointed toward the water. Exhausted, we needed to put our stuff down and physically couldn’t make it to the side of the island we most wanted to fish. The wind was pushing in hard on the northeast side, but we settled for a nook along the southwest for both comfort and convenience with our mother-load of cargo. Our planning wasn’t very well thought out in that regard.
Oh well— there were boulder fields everywhere.
We planted our excess gear along a hidden trail and descended a narrow gully down a rock face toward a seemingly endless stretch of boulders, coves, and most importantly, whitewater. The water on this side of the island wasn’t choppy, as the cliffs served as protection from the wind, but the waves were 3-4 ft. and crashing to form some beautiful whitewater. The weather was quintessential autumn—foliage, a crisp breeze, and bright warming sun. I was officially psyched; finally, it was time to start relentlessly heaving plugs and covering as much ground as possible as a squad.

Almost as soon as the group split to start casting, Billy hooked up on his yellow pencil popper. It was a nice fish that murdered his plug, but after a nice run, she was gone. I knew this would be good trip right then and there. We’d been fishing for 5 minutes and already had on a 20-pound-plus fish. There were more to come.
Over the next hour or so, the five of us were getting semi-frequent action, although I had yet to get a fish to connect on my white pencil popper. I was enticing the occasional swirl behind my lure, but nothing like the aggressive hits I was seeing for my buddies. I switched to 9-inch rigged black Slug-go and continued hammering the whitewater to no avail. I even tried a bunker-colored needlefish and spook, neither of which triggered so much as a rise. Meanwhile, my surfcasting companions were all catching fish in the 28- to 34-inch range — they were all using yellow.
My college buddy Dave, who just started fishing seriously this year, caught a personal best 36-inch bass at high noon on a yellow popper. The others were getting nice hits every 10 minutes or so on yellow pencil poppers of various brands. I was done trying to be cute and stick out; I wanted to get on the board, so I switched to a yellow Guppy pencil popper that I had barely used in the past.
Things picked up for me— I immediately caught two smaller fish that hit very close to shore. As the tide flooded the boulder fields and the afternoon crept in, we were all getting the occasional hook up. Every 5-10 minutes you’d hear, “fish on!” From 12-2pm we each landed at least one fish of the 30- to 35-inch variety and a handful of others in the 25- to 30-inch range. The hits weren’t constant, but if you kept your line wet and were using a yellow lure, the strike would eventually come. The best part was these fish were leaving no doubt when they hit, with violent topwater explosions that you dream about as a surfcaster.
We continued covering ground to hopefully find a honey hole with the cow we were searching for. Thanks to Bret, we found that spot. Albeit it was short lived, but we enjoyed a thrilling few minutes together.
He had walked far ahead of the group with a look of conviction to an untouched set of boulders. Soon after, he shouted to us, and from 100 yards away I could tell the fish he had on was big, very big. I grabbed my GoPro camera and sprinted across the pebbly beach to hopefully get some footage of this fish. As I arrived on the scene, I saw that Bret had already wrangled the bass out of the boulders and was in the process of lugging her onto shore with an oncoming wave. He was playing it perfectly. He had gotten past the hard part, but at the last second, the lure popped. Fish gone. Damn it!
I immediately started pounding the same water, flinging my pencil popper in every direction. I danced my plug behind every boulder I saw, making sure to hit as much whitewater as possible. The Guppy pencil popper can really launch, which gave me the ability to hit a large expanse of structure and multiple patches of whitewater as waves crashed over the boulder field. Bret’s hit happened close to shore. Mine hit at the top of my cast, in the sudsy water surrounding a subsurface boulder about 80 yards off shore.
Billy had been behind the group, and while catching up he witnessed the crashing bass annihilate my plug. He screamed, “Woah! Danny’s got a big boy on, fellas.” All went silent as I fought hard to keep the fish from taking me into the rocks. It hit directly behind a boulder, and I was convinced I didn’t have a chance. I lifted my rod tip as high as possible to keep my line from grazing one of the many boulders between me and the bass. After thrashing on the surface, the fish made several screaming runs. Miraculously, I was able to maneuver the fish between several large rocks and could sense its exhaustion as it neared the shoreline. I patiently waited for the right wave and used its force to guide the fish ashore. I was relieved and tingly with adrenaline. Surfcasting euphoria at its finest.
The fish measured 46 inches and bottomed out my 30-pound Boga Grip with ease; we didn’t get the weight of the fish, but she was a true fatty. The five of us admired the monster bass in bliss and snapped a few photos. I hurried to get her back in the water, in awe of the fish’s beauty as I revived it. With a strong jolt of her tail, the majestic beast swam off. What a feeling to release such a gorgeous fish.
The remainder of the day was not as fruitful fishing-wise, but we were riding high from the afternoon. As night came over the island, we set up a small camp on the beach with a roaring fire and laughed. “That was special,” said Phil. Life was good.
The night bite involved about a dozen bass taken on darters, the majority of which Bret caught with his black Super Strike. These fish were all above 26”, a couple touching the 30- to 33-inch range. We probably could’ve fished harder that night and explored the island more thoroughly, but we were utterly spent and wanted to make sure we were ready for a productive morning. We fished until about 2 am and finally hit the sack. I burrowed myself in my 4 sweatshirts and two pairs of sweatpants, doing my best to get some shuteye. If not for the cow I caught earlier, this was the worst sleep of my life. Amazing how a big bass can change that.
The following morning a cold front rolled in, and I couldn’t bear being pressed against the frigid ground any longer. I popped up before sunrise with wind howling in my ears, and fueled up on a Cliff Bar and some water. We were back on the same stretch of rocky beach that rewarded us the day prior, only the tide was low and there were no waves to speak of. It turned out to be a lifeless morning on the water.
At this point it was 7:30 am Sunday morning and our ferry was leaving at 2 pm, giving us about 6 hours to make the remaining day count. Even after a dead morning, we had to grit out the next several hours and keep going. We knew we wouldn’t be back here until the following spring.
The next several hours were quite the grind. We had slept no more than 2 hours and had been walking or casting for a day straight. On this day the fish were not cooperating and our energy was waning. The clock ticked past noon and we had only seen a couple swirls behind our lures, no takers.

This was ok in our eyes. We had been rewarded with an amazing Saturday and felt like it was only right to leave empty handed on Sunday— a welcome repayment to the fishing Gods. We conceded to the poor fishing and packed up our belongings to make the haul back to the ferry, giving ourselves plenty of time for frequent rest stops. By the time we arrived at the dock, it was 12:45pm, giving us about an hour before departure. Time to take out the gear for one last session.
The water surrounding the ferry was the last place on the island I’d choose to fish. It was just flat, motionless water. I’m sure there was underwater structure, but nothing about this venue looked remotely fishy, except that on my third cast I got a solid wack. Apparently there are fish everywhere on this island! We saw a couple more tail slaps, but nothing connected.
The clock quickly hit 1:30 pm and it was just about time to wrap things up. At that moment, Billy came running down the beach toward me, magically with a 12-inch live pogy in hand…that he snagged! Turns out Billy had been trying to snag a singular pogy cruising the shallows for some time, and he finally did.
We were running out of time, but Billy was determined to get a nicer bass, as yesterday his biggest bass came off within minutes of our arrival on the island. I quickly tied on a large circle hook for him, and he sprinted back toward the water with the wounded pogy on his line. We all chuckled. The giant pogy looked hilarious as it weighed down on Billy’s fishing pole. He lofted a cast that traveled no more than eight feet.
While the rest of us laid around counting down the minutes until we had to leave, Billy stood concentrated on the water when his pogy began fluttering on top. I could see it from a distance creating a wake on the surface. Man, was it pretty.
Minutes before the ferry arrived, I heard that beautiful shout from Billy that could only mean one thing: there’s big a fish on the line! I saw that the fish must have hit only a few feet from shore, as it thrashed violently in the wash. You could see its size from afar— another good one. I sprinted over with my GoPro filming and was able to document the landing and release of the fish, and what a beauty it was. The clean 41-inch bass was light in color presumably from having spent a lot of time on sandy bottoms. She weighed 26 pounds, a personal best for Billy from shore.
I documented the release of the fish and we shared high fives all around. The other group of surfcasters on the island had witnessed the display as they waited for the ferry and came over to congratulate us. Our two groups merged, and the eight of us walked to the ferry sharing stories of what was a special trip for everyone. They had also caught several large bass and a bevy of smaller fish. We were all little kids in that moment. Time stood still.
See you in June, Cuttyhunk.

