Fundraisers are challenging, yet some organizations display uncanny creativity in raising funds and pleasing the populace. This special edition of LEEP Happenings highlights several highly successful, interesting, funky fundraisers worldwide.
Many people are familiar with the annual Girl Scout cookie drive, the Salvation Army Christmas kettles, the Live Aid concerts, Giving Tuesday, and Red Nose Day. Each is well-known, iconic, and infinitely successful. Below are some lesser-known fundraisers that epitomize creative fundraising. I also covered several amusing onsite events and fundraisers in 2022's April issue, Onsite Unusual, including the Idiot-a-rod, and the Brisbane Cockroach Races.
We'll start with the fundraiser that left me rolling in laughter, The Great Willy Waddle. Read on; you'll understand why!
THE GREAT WILLY WADDLE
Date: May 18, 2023, in London
June 17, 2023, in Edinburgh
Location: United Kingdom
Champion: Orchid
Purpose: Fundraiser for Male Cancer Research
How do you get men to take male cancers seriously? You throw The Great Willy Waddle fundraiser!
The two-kilometer run or walk in Edinburgh, with a brotherly event in London, is a favorite with groups and cancer survivors. Participants wear inflatable male membrane costumes (which participants get to keep). Once everyone is appropriately attired in inflated willies, each participant waddles, jogs, or walks through Holyrood Park in Edinburgh, Scotland, or Queen Elizabeth Olympic Park, London. Wow! What a sight! Hundreds of willies waddling through the wetlands, woods, and willows near Wilfrid Terrace or Westminister. Whoopee!
Willies waddle for sponsorship dollars, with all funds supporting Orchid's research into male cancers and helping those with it. Open to participants aged 16 years or over.
CRY ME A COCKROACH
Dates: February 1-13, 2024
Location: Worldwide
Champion: San Antonio Zoo
Purpose: Raise funds to safeguard wildlife worldwide
The San Antonio Zoo is on to something with one of the most creative fundraisers. Animals have to eat, and people need closure. Cry Me a Cockroach solves both issues. Between February 1-13 each year, people with bad break-ups, brutal bosses, cruel colleagues, or obnoxious humans purchase a cockroach, leafy plant, or rodent and have it named for the difficult person. On February 14, the zoo feeds the named delicacies to the animals. Chomp, chomp, chomp—closure.
Funds raised support the zoo's vision of securing a future for wildlife in Texas and worldwide. To participate and join in the fun, donate as little as five dollars and symbolically name a cockroach, rodent, or veggie after you're not-so-special someone.
CANINES UNCORKED
Date: August 5, 2023
Location: Portland, Oregon, United States
Champion: The Portland Humane Society
Purpose: Raise funds to support and rescue animals in the Portland-Vancouver metro area
Someone got innovative and mixed wine, dogs, and dog lovers together for a wine-tasting event to raise funds for the Oregon [Or-ah-ghen] Humane Society. Oregon is known for its Pinot Noir wines specifically.
Canines Uncorked wine tour highlights north Willamette [Wil-la-met] Valley wineries where dogs are the guests of honor. A “License to Taste” passport includes free wine tastings at each winery, dog activities, and two complimentary tasting cards valid at all participating wineries in August. This event is a benefit for shelter animals. For beer lovers, see September's Pug Crawl.
Cheers!
HUSTLE CHICAGO
Date: February 25, 2024 (estimated)
Location: Chicago, Illinois, United States
Champion: Respiratory Health Association (RHA)
Purpose: Raise funds for and awareness about lung health
Hustle Chicago is a popular fundraising event where sponsored participants climb the stairs of a prominent skyscraper. Funds raised promote lung health, support those with lung disease, and fund research. The annual race is to the top of one of Chicago's iconic buildings, such as the Aon Center, John Hancock Center, or Willis Tower. Individuals and teams of climbers scale between 94 to 105 floors (approximately 1,632 to 2,109 steps) to reach the top of the building.
Good thing it isn't the Burj Khalifa!

FORGET-ME-NOT DAYS
Date: June 21, 2023
Location: United States
Champion: Bankers Life and Casualty Company
Purpose: Raise funds for Alzheimer's research conducted by the Alzheimer's Association.
Forget-Me-Not Days joined The Longest Day, the Alzheimer's Association's annual fundraiser on the summer solstice in 2019.
Forget-Me-Not Days began with Bankers Life and Casualty Company, the national life and health insurer, in 2003 as the company's annual fundraiser to benefit the Alzheimer's Association. Bankers, agents, employees, and association volunteers hit the streets nationwide wearing distinctive green aprons and handing out packets of Forget-Me-Not seeds to raise awareness of the disease. One hundred percent of the donations collected benefit the Alzheimer's Association.
Since 2003, Bankers has helped raise millions for the Alzheimer's Association through this fundraiser, and gardens have gotten much brighter.

GLOUCESTERSHIRE CHEESE ROLLING COMPETITION
Date: May 29, 2023
Location: Cooper's Hill, Gloucestershire, United Kingdom
Champion: Community of Brockworth
Purpose: Free event supports the village and has been a tradition for hundreds of years.
All you need is a seven to nine-pound ball of cheese, good running legs, and a sense of humor for the 300-yard downhill race on the last Monday in May.
The Gloucestershire Cheese Rolling Competition occurs annually on Cooper's Hill, near Gloucester, England. Participants chase a round of Double Gloucester Cheese down a steep hill, and the first person to cross the finish line at the bottom wins the cheese (and bragging rights).
The competition became official during the 19th century and has since become a beloved and iconic event in the region, attracting participants and spectators worldwide. Cooper's Hill is known for its steep and uneven terrain making the competition dangerous. Spectators watch participants tumble, trip, and slide downhill, chasing the rolling cheese. Several people are injured each year.
Who and why it started is unknown (though ale was likely involved). Gloucestershire Cheese Rolling is a tradition from the Roman occupation nearly 2,000 years ago.
The village of Brockworth champions the event, and though technically not a fundraiser, it is a critical event in supporting local businesses each year. The event was canceled in 2010 due to safety and insurance concerns—but that didn't stop it. A fan favorite, over 4,000 people head to Cooper's Hill yearly to celebrate the "running of the cheese."
THE JOSH FIGHT
Date: May 20, 2023 (estimated)
Location: United States
Champion: Josh Swain
Purpose: Laughs and to raise funds for Children's Hospital & Medical Center Foundation
"Who is the top Josh?" College student Josh Swain asked this question on Twitter as the COVID pandemic engulfed people's lives. What started as a silly joke in 2020, challenging men and boys named Josh to pool noodle duels and a winner-take-all rock-paper-scissors contest, became a highly popular fundraiser.
The first Josh Fight was held in 2021 and drew 1000 people and 50 participating Joshes from around North America. A four-year-old took the "Top Josh" title and received a Burger King crown and a mock wrestling belt. The second Josh Fight occurred in May 2022, with thousands attending and significantly more Joshes. It raised over US$20,000 for Children's Hospital. Josh Vinson Jr, the four-year-old from the previous year, retained his title of Top Josh in 2022.
The Josh Fight is one of the world's most creative fundraisers, and it's also straightforward to duplicate anywhere in the world. Is anyone up for a Sarah Supreme, Matchless Mohammed, or Joust of the Georges?
Fundraising for 2023 has started, but this year's event date and location have yet to be announced.
PLANET PRANCER
Dates: July-August (estimated)
Location: United States
Champion: Anti-Slavery International [US Prance]
Purpose: Raise money for different charities through long-distance dancing.
London teacher Ben Hammond uses his summer recess to prance and dance for charities. He came to my attention in 2018 with his ambitious attempt to cross America (over three summers) along historic Route 66 to raise awareness of the 40 million people worldwide currently enslaved. In 2018, he pranced over 1,400 miles (2,253 km), beginning in Santa Monica, California, and ending in Gallup, New Mexico.
He explains his US prance's purpose.
"I'm raising funds for Anti-Slavery International because to me, modern-day slavery—such as human trafficking, forced labour, debt bondage, child slavery or descent-based slavery—is one of the biggest evils that exists today. I believe everyone should have the right to live a life free from servitude, to determine their own future and to create and follow their own dreams, just as I am lucky enough to be able to do."
Hammond is the world's first long-distance dancer, and he's been using his talent and tutu since 2011 to dance over mountains, nations, and cities to raise funds for various charities.
COVID-19 (and getting married to his wife during it) stopped his 4,000-mile trek across America for a bit. However, Hammond prances for a charity each year somewhere in the world—just he, a powerful set of legs, and his signature yellow tutu. Follow him on Twitter @planetprancer.

THE GARAGE SALE TRAIL
Dates: November 11-12 & 18-19, 2023
Location: Australia
Champion: Government of Australia
Purpose: Reduce landfill waste, support the environment, and raise money for families and charities.
Created in 2009 as a local promotion in Bondi Beach, the Garage Sale Trail is a free event that attracts over 300,000 bargain-loving shoppers nationally. It is Australia's fundraising and second-hand awareness extravaganza featuring over 15,000 garage sales and stalls nationwide.
Garage sales and yard sales are a modern twist on the dock sale tradition (rummage sales), where ship owners sold their unclaimed cargo quayside [key-side] to the public. In modern times, people use their yards or garages to sell items they no longer use, typically on a weekend. Garage and yard sales are a great way to make a little extra money and recycle items to people who will use them. For buyers, they can be a treasure hunt. On occasion, people sell items of great value without realizing it.
With over two million pre-loved treasures on offer each year, Australians refer to the Garage Sale Trail as "our national day of haggling," often accompanied by barbeques, street parties, and neighborhood festivals.
Various locations support different charities or individuals and families. Aside from raising money, the event supports the planet by preventing items from clogging landfills and using energy and resources efficiently by giving used goods a second life.
TRICK-OR-TREAT FOR UNICEF
Date: October 31, 2023
Location: United States & Canada
Champion: UNICEF USA
Purpose: Raise funds to help children in crisis around the world. UNICEF is a program of the United Nations.
Trick-or-Treat for UNICEF is an annual fundraising campaign organized by the United Nations Children's Fund (UNICEF) during the Halloween season in the United States and Canada. The campaign encourages children to go door-to-door in their neighborhoods and collect donations for UNICEF as they trick-or-treat for candy. Rather than just saying "trick-or-treat," participating school children say "trick-or-treat for UNICEF."
For those unfamiliar with Halloween traditions, trick-or-treating originated with the Celts over a thousand years ago during the pagan festival of Samhain. It became an American Halloween tradition during the early 20th century. To participate, children dress up in costumes and go from house to house in their neighborhood, ringing doorbells or knocking on doors and asking for candy treats (so they don't play a trick on the host). The children usually say "trick-or-treat" to the person who answers the door. This person then gives them candy. By the night's end, each child has a big bag of candy.
Halloween and trick-or-treating are a big deal in the United States and Canada.
HOW UNICEF'S FUNDRAISER WORKS
Traditionally (when I was a kid), each house had a roll of coins next to the candy bowl on Halloween. When costumed children arrived at the door, a few coins would be added to each child's orange UNICEF box before dropping candy into their pumpkin-shaped buckets. On the school day following Halloween, all the children bring their UNICEF boxes to their teachers, who collect them and hand them to the school, which tabulates the donations and issues a check to UNICEF.
In recent years Trick-or-Treat for UNICEF has gone high-tech. In addition to the orange boxes for collections, many schools set up online fundraising pages to collect donations from people who prefer to give electronically, and it's just as common to see a child with a QR code as the iconic orange box.
The campaign began in 1950 with a group of children in Philadelphia who wanted to collect money for children in need worldwide. Since then, Trick-or-Treat for UNICEF has become a popular tradition, raising millions of dollars annually to support UNICEF's programs in more than 190 countries and territories. The money provides lifesaving vaccines, clean water, nutrition, education, and emergency relief to children worldwide.
RNLI FISH SUPPER
Dates: October 1-15, 2023
Location: United Kingdom
Champion: Royal National Lifeboat Institution (RNLI)
Purpose: Support the sea rescue work of the RNLI
The RNLI Fish Supper began in 2014 and is an annual fundraising event supporting the work of the Royal National Lifeboat Institution (RNLI), which provides 24-hour lifeboat search and rescue services for the United Kingdom and Ireland.
Registered participants host fish-themed dinner parties and donate the proceeds to the RNLI. The RNLI website includes a free fundraising kit with resources, including recipes, invitations, posters, and donation envelopes.
Dinners typically occur in October around RNLI's Fishermen's Safety Week, an awareness campaign focusing on safe deep-sea fishing practices.
The RNLI Fish Supper has raised over £2 million (US$2.5 million) for the charity. It is a fun and delicious way to support the lifesaving work of the RNLI and enjoy a meal with friends and family.
The United Kingdom and Australia each have several events similar to this, where eating or drinking together in private homes raises funds for causes. In both nations, the fundraisers are quite successful.
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THE WRAP OF IDEAS
Each highlighted fundraiser is successful and easily adapted to different cultures and norms. For example, Canines Uncorked could be adapted to:
Toddlers with Tea—parents with small children socializing and raising money via tea tastings.
Coffee for Catnip & Kibble—to raise funds for animal rescue through coffee shops and boutique roasters.
What about Pastries for Parents— to support single parents, hosted by bakeries in a city, anyone?
The Willy Waddle could be the Floaty Roll —floaty arm-banded walk down the corniche to promote water safety.
Use anything that rolls for a chase akin to the Gloucestershire Cheese Rolling Competition—which I'd love to see a sports protection gear company or bone health non-profit sponsor as a fundraiser—it would be a natural.
A library, school, or university could have a Book-building Contest as a fundraiser. Books are a little like blocks or a deck of cards—imagine the possibilities. How high before that house of books falls?
Those are just off the top of my head. Fundraisers don't have to be boring, especially if you get creative! I hope this issue stimulated some ideas.
Thank you for the gift of your time! I really appreciate it. Please like, share, subscribe, and comment if you can. The next issue will cover events in May 2023.
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