Up until last May, I hadn’t caught a winter flounder in 29 years. As a child growing up near Boston, I was a boy-wonder flounder-catching kid, and I spent countless summer days on my father’s boat drifting around and filling buckets full of these tasty little flatfish.
But my father died when I was 11 years old, his boat was traded in for a swimming pool, the flounder stocks collapsed, and I would enter a decades-long flounderless funk.
The winter flounder have made a miraculous revival in Boston Harbor, and last weekend I received an invitation I simply couldn’t refuse. Captain Jason Colby had an open spot, and extended an invitation out to the On The Water crew. I was all over it. I joined up with On The Water contributing writers John D. Silva and Ron Powers, and we spent the morning prowling Boston Harbor in search of my old friends.
It was a cool, dank and foggy morning. We cruised out of Quincy Yacht Club and ran through a series of islands, channels and bridges until we ended up near the Deer Island Flats. It had been a long time since I’d ventured into Boston Harbor, and I have a newfound respect for the beauty of the harbor, and the miraculous clean up that has occurred since my last visit.
I didn’t take long to hook up the first flattie. Russ Eastman of Monahan’s Marine was also aboard for the trip, and he was the first one to hook up. We were all using light conventional combos, which made the fishing a whole lot more fun than I had remembered. As a child, we always used heavy, clunky boat rods and dacron line, and sometimes you couldn’t even tell when a fish had taken the bait. Drifting in shallow water with light tackle makes the whole experience more enjoyable.
Captain Jason Colby’s boat is a Gold Line hull, it has plenty of a deck space, and it’s an “all business” kind of boat. We could easily fish 5 guys on the rail as we drifted. I especially like the fact that Jason has added rodholders in just about every conceivable location on the boat.
The Captain connected with a keeper flounder that would join the “varsity team” in the cooler. Once the tide began moving, the bite picked up dramatically. We began a steady pick of keeper-sized flounder. We didn’t get any whoppers, but we had very few throw-backs.
Despite it being a Sunday morning, there was not much of a crowd on the harbor. Fishing on Mother’s Day is always a good idea if you’re looking to get away from the crowds.
Although we did catch a few fish on clam strips, sea worms were the bait of choice for most of the flounder we sampled. Simply putting half a worm on the hook is all you need. Ron was kind enough to share a few of his homemade Zobo rigs with me, and they worked very well.

The final tally was 29 keepers in about 4 hours of fishing. Not bad for a drizzly Mother’s Day morning. I would surprise my Mom later that day with some tasty flounder fillets, freshly plucked from the sea.
I fried some up. They came out delicate and crispy, nicely browned. They tasted like I remembered… simple and delicious. I ate them with ketchup, for old-time’s sake.
Special thanks to Captain Jason Colby of Little Sister Charters. If you’re hankering to catch some flounder, I highly recommend him, you will not regret it. He’ll be running open boat trips on Tuesday and Thursday mornings for the next month, which is a good affordable way to get in on the flounder fun.
www.littlesister1.com
South Shore Flounder Fishing
For additional flounder tips and information check out our guide to South Shore Flounder Fishing.


Back in 1977 or ’78 I was invited out on a friend’s boat for a flounder trip in Boston Harbor. In a few hours we caught enough flounder to fill a 40 gallon garbage can.
Matt, is that why flounder stocks collapsed?
No, it was because of pollution in the harbour.
Ron I was wondering on your zobo rig how would you attach your main line to the esca light? It looks like it’s a key ring. I don’t know the technical term
Boys and Girls,
The limit (north of The Cape) is 8 fish/person over 12 inches. Usually the fishing is good enough for you to release anything under 14 inches and still limit out. Using “bigger hooks” like size 2 or 1, beak or khale prevents the smaller fish from being hurt so you can return them with a free conscience.
Ron attaches his ESCA with a stainless steel split ring and any kind of “small glowing gizmo” will help when the sky is overcast or the water is cloudy.
Good Luck!…..Jason
Great article and video! I’ve been lucky to have fished with Captain Colby a number of times, and have to say he runs the best charter boat in the Boston area. Never been disappointed, great guy, and he usually has great people aboard which makes for a fun trip! Can’t wait!
What color Esca light do you use
Nice to see and hear of fish coming back to your region or any region for that matter..!..
Since 2013, when Paul Diodati (Then DMF Director) doubled the commercial daily quota in Ma. State Waters the fishing has been dropping off dramatically each year. As of 2018, the fishing is less than 25% of what it was 5 years earlier. These fish simply cannot withstand intensified dragging. Boston Harbor and the surrounding bays and estuaries are the last place in the world where there is a viable inshore population of these fish and David Pierce, the current DMF Director needs to be made to understand that is makes no sense to net up the last of the winter flounder population.
ALL of these fish come at the expense of the recreational fishermen who had been utilizing them in increasing numbers throughout their recovery (1999-2012) with more and more people fishing for them and yet more and more (and bigger and bigger) fish available each year. It is obvious that the rec fishermen were not hurting the recovery but as soon as they increased the dragging the numbers (and sizes) went right down from there.
Call David Pierce’s office (617-626-1520) and tell him to stop the netting!