September 30, 2022 7 min read

Team Cheeky Fishes the Great North Woods

Team Cheeky takes a few days off for a team retreat in the Maine woods and were treated with heavy rains and a shower of fish. As we prepared for our annual team retreat, the only person who really knew what to expect was founder and CEO Ted Upton who has fished the Magalloway River for most of his life. Thank you to Wendy and Mike of Bosebuck camps for being such wonderful hosts.

“It was where I learned to fish and it was a real full-circle experience to share this place with the team,” Ted said.

With every fishing trip each angler takes away something different. For Team Cheeky this was no different. We have a wide range of anglers across our company from the novice to the well-traveled experts. Read how each of them viewed the trip.


Emma (Shipping): I had a few goals before the trip. One was to catch my first fish on a fly. I have only recently started fly fishing.  There were so many obstacles to overcome for me. I live around the woods, but this was different, no cell coverage and no people. The first tributary we went to was amazing. We crossed the stream and I just looked around thinking of wow. What a beautiful place. And then I caught the fish, my first native brook trout and first trout on a fly. All the hard work paid off. The trip really opened my eyes and makes me comfortable to step outside of the box knowing that I have such a great team around me there to support me.  


Walker (Sales):  I fish a lot and have a bucket list. Catching a native brook trout over 15 inches has been on the list for a long time. When we first got up there, I was skeptical that was going to happen with the water conditions being so high. But I was able to accomplish that right in front of the plaque commemorating President Dwight D. Eisenhower, who fished the same spot. I caught it right below Little Boy Falls on my Euro nymphing rod with a stone fly jig pattern I tied just for this trip. It was a pattern of my own creation. The big landlock salmon were something special as well. They will eat a dry like a brookie, a streamer like a brown and jump like a rainbow. What more could you ask for? I loved being there as a team, standing on the dock at night when the clouds parted and you could see every star, planet or satellite. I think Maine is a top 5 state for the outdoors. When we fished the small tributary, it was just knowing that we are one of just a handful of people who have fished that ever. There is so much to explore.


Ellen (Marketing):  When we first rolled behind the logging gates and ran into that logging operations I was just mesmerized. That machine, that we just called the De-limber, was so powerful and dexterous. It effortlessly picked up the trunk and with no effort shredded the limbs off and cut to length. It was like something out of a movie. I had no idea. The one night on the dock we saw a shooting star and I made a wish that I didn’t tell anyone - I wanted to catch and net a truly big fish all on my own. We have such a great group who are always willing to help out, but after losing a number of big salmon, I was determined. Before the trip I was focused on my favorite fish, the brook trout. I had no idea about the salmon and they were tough on me at first, throwing the hook or breaking me off. The next morning, I was down in the pool and it all came together. A big fish ate and I was able to bring it all the way in and net it myself.


Jack (Customer Service):  I fished the Magalloway a lot when I was in college, but I had only been on the lower section of the river and never had access to the water above the locked gates. The traditional pools were special and I had a ton of fun. I learned a ton from Ted. We had one session where we were aggressively wading down together and catching salmon on every cast. You could see the fish hunting in packs. Sometimes you think you are getting really good at fishing and you realize that there is still so much to learn. When we were having our epic session, I was so focused on the fish that my net slipped out of my pack and I didn’t notice until it was floating away. I made a great cast and hooked it, but the water was ragging and it broke the line and I could not retrieve the net. I didn’t even care at that point since the day was so incredible. I know someone will have a good day when they find a brand-new net downstream. One of my favorite things about the trip is how the team came together in a kind of collective mission. From novice to expert, we all had a special time in a really special place. I think we all came away from it understanding how special it was to be fishing for native brook trout and wild salmon and how important it is for us to be advocates for these types of places.  


Ted (CEO): This river is where I learned to fish and it has special meaning to be able to take the entire team up there. It is kind of full circle for me and one of the best memories I will have of the company. Being able to share a new location and a new way to fish is one of the great joys of fishing for me. I will have to say that I was a little startled when we got there. I had never seen the river so high. It is the only time ever that it was too deep to access some of my favorite pools. It was amazing how fast it dropped and boy did the fishing turn on. I was fortunate enough to share a really special moment with Jack, a very new employee. We were at one of my favorite pools and Jack and I landed 10 large salmon in about 30 minutes. We were netting each other’s fish. It was fast and furious. We even took a couple little tumbles. The next day I fought a large salmon down a riffle where I had to follow it from a pool above. Chasing the fish and finally falling in the water. But I kept the tip up and was able to net my largest salmon of the trip. It was a treat to share it all with the staff. We spend so much time together, more than our families in some cases, and to be able to just relax, fish and share a special place with them really felt full circle.


Sam (Operations):  First of all, it was such a great community effort. We were all helping each other, sharing tactics, netting each other’s fish. We all wanted to see everyone catch fish. Right away it was apparent my tactics were not going to work. I had to adjust. As humbling was, it was fun to do something I don’t normally do. At one point, Ted came and found me and took me down to a lower pool. After two casts, with Ted’s tactics and his flies, I landed a big salmon. Usually, people come to me for my fishing knowledge, it was good to see Ted’s local knowledge help me overcome the adversity. I had never been up there. It was so different. It felt like Ireland. The salmon where amazing. They look like winter browns, but they had such a boney mouth there were hard to keep hooked. Our team gets along so well, that it is just effortless to hang around with each other.


Scott (Sales):  I had a trip planned with some buddies 15 years ago to the exact same lodge. We were going to do some fishing and wing shooting, but it got canceled. It has always been on my list. When I was about 7 or 8, I was in the Rangely area and had a cardboard cutout of a brook trout. I had been waiting to get back ever since. Seeing this place and getting behind the gates was special. I loved seeing some of the younger folks be so remote. No Cellphones, no problem. For Ted, Peter, and I we have been a lot of places and caught a lot of fish so seeing, for example, Ellen finally landing her first salmon after losing a few was so cool. I will also remember my leaky waders. My left leg was fully soaked for 3 days. I think I need a new set.


Peter (Marketing):  My two favorite things about fishing is exploring new places and sharing my knowledge. I was able to do both on this trip. This was new country for me. The dense forests and the trees just coloring up made the surrounding magnificent. And the mushrooms!!! I am a bit of a mushroom guy and to see so many varieties below the canopy was amazing. The tannins in the water added to the mystery an made my first ever landlock salmon feel even more mysterious. My favorite moments were helping Emma, who is newer to fly fishing, take huge steps on her journey. One morning our crew started at a small tributary. We crossed a rickety old wooden bridge and split up. Emma and I waded up a few pools. She had been asking about how to play a fish. I have an old guide trick I used to use when introducing people to the sport in my two decades of guiding in Montana. I grab the line and make the angler land me before they get a crack at a fish. After the tutorial we walked up another pool and she caught her first trout on the fly. A native brookie on a dry. That was such fun.