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Cheeky Schoolie Tournament: Lucky Number 13

What does it take to throw the world's largest fly-fishing tournament? Here is an inside look at the Cheeky Schoolie Tournament, presented by Simms.

Cheeky Schoolie Tournament: Lucky Number 13

The world’s largest fly-fishing tournament celebrates its 13th year of fellowship and conservation this year. (Photo courtesy of Cheeky Fishing)

It’s 5:30 tournament morning. The mass email with team numbers–indicators of teams that are Sharpied on to the official tournament rulers–is just hitting inboxes. Cheeky staff are bleary-eyed but pumped that everything is going off without a hitch: All 275 teams have what they need for their day on the water. And just like that, the world’s largest fly-fishing tournament, the Cheeky Schoolie Tournament, is under way. But let’s rewind and see just how this tournament comes together.

The History

It all started 13 years ago when the founder of the tournament and CEO of Cheeky Fishing, Ted Upton, sent a note out to a bunch of friends and striper bums to meet at West Dennis Beach parking lot. They all threw in $20 with the winner taking home the pot, minus a few bucks for beer money.

“We just wanted to have fun and get together and fish,” recalled Upton. “I had no idea just how far it would go.” From that dusty parking lot to the world’s largest fly-fishing tournament, Schoolie, as the tournament is affectionately known, has taken on a life of its own.

In the early years it was a looser format, but the magic formula was around from day one. Wade fishing only. Catch, photo, measure, and release, counting the inches of your team’s four longest fish. The teams of two were an early addition, and the boundaries have always been Cape Cod–east of the canal, all the way out to the tip of Provincetown.

At first, everyone fished all together at the same place, but as the tournament started branching out, people started looking for new water. Locals fished it too, slinking off to their secret spots.

Upton soon decided to split the pot–half going to the winner, the other half going to beer and food. When he noticed a few bucks left over, he decided to donate it for the good of the fish they all loved. Stripers Forever was the first recipient.

Taylor Varna of Stripers Forever cites Schoolie as keeping the lights on in some lean years for the organization, whose mission is to get striped bass listed as a gamefish which would give the species far more protection under federal and state law.

The Magic

Part of the magic is the low barrier to entry. If you have a fly rod, a fishing buddy, and $250, you can fish Schoolie. This is a far cry from a Florida tarpon tournament with high-priced entry and even higher-priced guides. At Schoolie, your entry fee is immediately recouped with a captain’s bag overflowing with gear from the most recognizable brands in fly fishing and the outdoors. Tournament registration opens at the beginning of February and typically fills in 4 or 5 days.

A fly angler casting in a bay, wading knee deep.
Rules for the tournament include wade fishing only; catch, photo, measure, and release, counting the inches of your team’s four longest fish; teams of two; and the boundaries are Cape Cod–east of the canal, all the way out to the tip of Provincetown. (Photo courtesy of Cheeky Fishing)

“It is kind of the everyman’s tournament,” a long-time tournament fisherman said recently. “And for New England striper fanatics, Cheeky (as many other people call the tournament) is the unofficial start of striper season. We mark the tournament on the calendars.”




Over the years, Schoolie has been witness to many anglers’ stories. There was the couple who fished the tournament together, saying it was their favorite yearly adventure. They are married now with the proposal coming in waders on tournament day. There are many father-and-daughter teams, mother-son teams, and just plain teams of misfits. Team names are funny and punny. There are even a few folks immortalized at the event. Not the winners, because no one really pays that much attention to that, but those like one angler named Bear, who always rallied a group to come and fish the tournament. Sadly, Bear isn’t with us anymore, but his friends vow to continue coming as a yearly remembrance of their friend. You might spot them fishing with their bracelets reading “Fish Like Bear.”

One stat that speaks volumes about Schoolie is the number of scorecards submitted. Last year’s tournament had the greatest number of scorecards submitted, beating the previous record by 15. The number was still only 84 entries. Why would only 84 of the 275 teams bother to put in a scorecard? Because the magic isn’t about winning, it’s about connecting with each other and supporting the fish. They come because it is fun no matter how many inches you log.

The Conservation

Schoolie is now run for conservation fundraising and awareness. All proceeds of the tournament are given to the conservation partners involved: Stripers Forever, Keep Fish Wet, and the American Saltwater Guides Association.

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Stripers are the great American fish. An early 1800s Massachusetts tax on the commercial harvest of striped bass was used to fund America’s first public school system. They were eaten by revolutionary troops, literally feeding the armies that freed us from the British. Fish migrate up and down the eastern seaboard, but also live in freshwater from Cape Cod to the California Delta. In the 1980s, striper numbers in the Chesapeake Bay, an important spawning zone, plummeted forcing a moratorium on fishing for stripers. With cooperation between environmental and conservation groups, the stocks were nursed back to health.

Two anglers in ankle deep water measuring a striped bass.
Because of suggestions from the Keep Fish Wet team, rules were changed so that fish under 20 inches are not measured for scoring and that the photographic evidence had to be taken at or below the waterline. (Photo courtesy of Simms Fishing)

Now, some 40 years later, we are approaching another critical juncture. Young fish are nowhere to be found with fish stocks plummeting to critical lows. States manage the fish separately, meaning as a fish crosses the imaginary line from New York to New Jersey, they suddenly do not have the same protections. Climate change and the decimation of forage fish like bunker are also contributing factors as is the threat to spawning grounds in the Chesapeake, the Hudson, and other crucial systems.

The Schoolie was named, kind of tongue in cheek, after these smaller fish that need the most protection. Every fall, the Schoolie tournament directors seek counsel from their conservation partners to talk about the fish stock reports to make sure that it is still prudent to have the tournament. So far the partners agree that the exposure the tournament brings, the money it raises, and the important scientific studies conducted during the tournament make the effort well worth it.

The conservation partners have been selected because they each bring something unique to striped bass conversation. Stripers Forever focuses on a grassroots effort to get stripers listed as gamefish–a lofty goal. They have been an important, local voice for science-driven management.

Keep Fish Wet advocate and educate for catch-and-release best practices. Catch-and-release fly anglers like to think that we have no lasting effects when we release fish. We are finding out that this simply isn’t true. Mortality of released fish could be 10 percent or higher. Shrinking this by even just one percent with better fish handling could save hundreds of thousands of fish. Keep Fish Wet, in partnership with the University of Massachusetts Amherst are conducting the largest catch-and-release study of striped bass ever undertaken. The tournament and Cheeky Fishing helped the University secure a prestigious Woods Hole Sea Grant to fund the study, and teams of scientists follow tournament anglers collecting data in hopes of furthering proper release practices.

A man filling out an oversized check.
The Cheeky Schoolie Tournament has donated more than $100,000 in its 13 years. (Photo courtesy of Cheeky Fishing)

The Keep Fish Wet team has advised the tournament on rules that help protect and educate anglers. Because of their suggestions, rules were changed so that fish under 20 inches are not measured for scoring. This helps decrease the handling of the smaller fish. Rules were also enacted that the photographic evidence needed for scoring had to be taken at or below the waterline. Tournament officials have enforced this, disqualifying teams that did not strictly adhere to the rules. The tournament is typically before Memorial Day when the water is still cool and better for releasing healthy fish.

The American Saltwater Guides Association (ASGA) is a young conservation organization that has quickly become a powerhouse in striped-bass-policy work. The organization advocates for the guide and angling community who make a living off healthy fisheries, and takes on Washington D.C. and Atlantic states to enact better, science-based fisheries policy. They have also worked with state agencies and scientists with studies of their own. Its recent Albie Project, with funds from Cheeky and Schoolie participants, has helped show conclusive proof of false albacore connectivity from Florida to Massachusetts. This should help states manage them as one migratory fish population.

Schoolie has given more than $100,000 over its 13 years.

The Grind 

Although the tournament goers might see a well-oiled machine, behind the scenes can be quite hectic. It starts with figuring out the date and finding a place to gather. For the past few years this has been the West End Restaurant in Hyannis. Blain, the owner, is a long-time Schoolie participant and turns his high-end restaurant into an angling hangout for the weekend. Sponsors are then secured to help with the killer raffle and captain’s bag items. Most have been with the tournament for more than half of the tournament’s life. This year, to include more brands, the tournament has opened up “Brand Wars” intended to allow any company in the fishing or outdoor space a way to participate and contribute.

People gathered around event tents.
The West End Restaurant in Hyannis becomes an angler's hangout during the tournament. (Photo courtesy of Cheeky Fishing)

Schoolie maintains its own website and uses apps for registration, communication, and scoring. Tech has made it easier with remote starts and better communication. Before remote starts, one of the greatest scenes of Schoolie was Ted standing on the roof of a U-Haul, shouting through a megaphone into a sea of hundreds of wadered-up anglers. The traffic jam created soon thereafter was a colossal headache. Remote start allows folks to spread out from the get-go. Although registration is capped, the Cape has plenty of room for anglers with over 1,000 miles of shoreline, canals, salt ponds, and jetties.

As the tournament draws closer, the Cheeky team has to start managing the auxiliary events that crop up. These include a women’s event, striper conservation symposiums, media junkets, and sponsor BBQs. Then comes the big nights including Friday night’s Captains Party and the Awards Celebration on Saturday night. This year Fly Fisherman magazine will be presenting its Conservationist of the Year award at the tournament.

Packing Captain’s bags–550 of them–is no small feat. This takes many days and a U-Haul to transport. A conveyor line of staff and local kids walk in circles filling bags with pizza-stained hands.

When tournament week arrives, the team has its game face on. The line for captain’s bag pick-up snakes around and into the parking lot of the West End. Saturday tactics are discussed in hushed tones. A sponsor village has been set and showcases the latest gear. People grab their free beverage and start to wander through. The Cheeky team is giving hugs to teams that have become friends. Most teams have been fishing the tournament for more than five years and many have been fishing for 10 or more. For many, it feels like “our” tournament. And they’re right. It is a tournament of the people and for the people.

The seasoned veterans go light on the beer the first night, knowing that they need to execute their plan to have a shot. Early morning comes and the Cheeky team is getting the last few people their captain’s bags and preparing to send the teams the all-important email with their team number. For the competitors, it all comes down to this. They have scrutinized the tide charts, selected the perfect line, and tied on the perfect fly. Hopes are high that it all comes together. The weather has thrown in its daily variable.

Three… two… one… GO!

While the competitors are in a flurry of high-energy fish finding, the Cheeky team, for the next few hours anyway, has a moment to relax and catch their breaths. Then it’s on to Instagram “Live Look-Ins” with some of the teams reporting on conditions in real-time. At the venue, AV is checked and final preparations are made so the awards night shines.

As the results start to roll in, the officials locked themselves in a room looking at scores. Photos are scrutinized and some tough calls are made. Finally, there is a list of the winning teams and a mountain of product to give away.

The hungry hoard starts to filter into the Awards Ceremony. Excited and weary anglers delight at sharing the story of their days, maybe even sharing their secret spot, which might’ve turned out to be barren of fish this year. Stories of the one that got away abound. Songs are sung, awards are given, and raffles are drawn. As the last goodbyes are uttered, breakdown commences. There might be a little extra zest from the Cheeky crew knowing that if they get it all broken down tonight, the team, finally, will get to spend Sunday fishing together.

Didn’t we start this so we could fish?  But there we are only T-minus 364 days until the next Schoolie.

Click here for more information. 


Peter Vandergift has been in the fishing industry since age 19. First as a guide and outfitter, spending 18 years shoveling water in Alaska, Montana and Wyoming. Peter then worked for industry stalwarts, Simms Fishing and Costa Sunglasses. He is now Chief Marketing Officer for North Point Brands whose stable of brands include Cheeky Fishing, RepYourWater, Wingo and RepYourWild. He has fished the Schoolie Tournament as a competitor, has been a sponsor, and has been Tournament Director for the past 4 iterations.

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