Ten Outside-the-Box Charity Challenges

While the classic charm of fetes and raffles will always endure, today’s world continues to surprise us with unique waves of fundraising trends. Creative ways to raise the bar are always on the horizon—from the ingenious to the wacky and everything in between.

So no need to sell candy or magazines or get pledges for that walk-a-thon! Here are ten charity challenges that were inspired by outside-the-box ideas.

Related: 10 Acts Of Astonishing Charity Performed By Ordinary People

10 Stop Playing That Song

It is an interesting twist on fundraising when the aim is to irritate people into donating—a simple but effective strategy adopted by Tenino High School in Washington. One day in 2014, the school began playing the Justin Bieber song “Baby” on loop at every break (during recess, at lunch, and between classes) as annoyed students donated to make it stop.

Students made comments like “my head is about to explode” and “I just want to go home.” The goal was to raise funds for disadvantaged orphans from Ghana, and the school almost doubled its expected target within a day and a half. The original idea came from students at Evanstown Township High School in Illinois, who launched their charity campaign “Stop the Bieber” in 2011.^[1]

9 Tower of Cupcakes

Baking cakes for charity has literally risen to new heights in modern times. In 2017, South African charity Cupcakes of Hope created a soaring 10.7-meter-tall (35-foot) tower of cupcakes to raise funds for children’s cancer research. The impressive (and delicious-looking) structure in Vereeniging, South Africa, was the result of local business support and a community baking drive. The cone-shaped frame held 6,370 carefully-placed cupcakes and weighed 1,200 kilograms (2,646 pounds). I wonder what the olden-time “cake sale on a card table” bakers would have made of this challenge, complete with endless crane journeys to set up and take down the display.

The quest was a fundraising success for Cupcakes of Hope, with boxes of cakes also gifted to children’s homes, hospitals, and volunteers at the end of the day. From 2017 to 2019, the charity also held the Guinness Record for the World’s Tallest Tower of Cupcakes.^[2]

8 Hands Across America

In 1986, millions of Americans participated in Hands Across America—a chain of people holding hands for 15 minutes spanning from New York to Los Angeles. Quite an achievement considering that organizers could not fall back on the ease of the internet or smartphones back then. The concept was developed by Ken Kragen (also a key coordinator of the famed “We Are the World” charity song of 1985) to raise money for American poverty. The chain crossed 17 states, with an estimated 5.5 million participants paying for their place in the line. U.S. President Ronald Reagan and a host of other prominent figures also joined in.

The ambitious idea of an unbroken human chain across a continent was almost achieved. With some breaks reported in Arkansas and areas of the Arizona desert, participants tried to compensate by using ribbons, buses, and livestock. When Kragen was asked in 2019 if Hands Across America could work today, he joked that people would be too busy attempting selfies now to actually hold hands.^[3]

7 Human Hamster Wheel

Crossing the Irish Sea inside a human hamster wheel may seem a tad overambitious for everyday folk. However, British endurance athlete and engineer Chris Todd is no stranger to big picture charity feats. After running six marathons in six days across the Gobi Desert in Mongolia and completing a Canadian Arctic hike, it was time for a new challenge.

Todd designed and built a giant steel paddlewheel supported by floatation on either side. With the help of family and friends in his garden in Bromham, Wiltshire, the clever contraption took almost a year to make.

In 2012, Todd set off on an estimated two-day slog from Wales to Ireland on the Tredalo (as he named the wheel). Apart from walking on water, his goal was to raise money for two charities he admired—the Wiltshire Blind Association and Royal National Lifeboat Institute. Planning for the adventure included a support boat team carrying over thirty liters (8 gallons) of water and sixty chocolate bars.

Todd powered through the first third of the 106-kilometer (66-mile) course in calm conditions. However, sometimes the best-laid plans are no match for mother nature. Unfortunately, harsh winds caused wave damage to the rudders, and the quest had to be aborted. On the positive side, Todd raised money for charity and made it quite a distance across the open sea in his unique invention.^[4]

6 Giant Waterslide

In 2013, two enterprising New Zealanders from a mental health charity, Live More Awesome, began their mission to build the world’s longest waterslide. Creators Jimi Hunt and Dan Drupsteen headed the original project—an arduous task of digging a 554-meter (1818-foot) trench into a hill, covering it with plastic and running water through the course. The original event was a great success, gaining worldwide media attention and starting more conversations around depression. Unfortunately, the following day was not much fun for Live More Awesome volunteers, who had to fill the massive trench on the farmer’s land.

Eighteen months later, Hunt and Drupsteen had designed, crowdfunded, and created a Plan B—an enormous, inflatable waterslide. Made from polyvinyl chloride (the same material as bounce houses), the impressive slide was 600 meters (1,968 feet) long and reached speeds of 53 kilometers per hour (33 mph) per hour. Weighing 6,500 kilograms (7 tons), it took three days to set up and one day to pack down.

From 2015 to 2018, the giant slide featured at three-day events at Jonkers Farm, near Bethells Beach, New Zealand. Enthusiasts flocked to the farm to ride it, all proceeds toward mental health initiatives. In 2015, the slide held the Guinness Record for the World’s Longest Inflatable Waterslide and later found a new home at Action Park in Vernon, New Jersey.^[5]

5 Stormtrooper Trek

Many have set off on long-haul walking missions to raise money for charity, but would they be willing to trek Australia as a Star Wars stormtrooper? Such get-ups were designed for a galaxy far, far away, not for rising temperatures and the never-ending Australian terrain. Australian Scott Loxley, however, was determined to complete his 15,000-kilometer (9,320-mile) Star Wars-style slog while raising money for the Monash Children’s Hospital in Melbourne. Loxley walked for more than 400 days between November 2013 and June 2015. He crossed remote regions of the Nullarbor Plain, the Kimberley, and Northern Territory before heading down the East Coast.

The roving stormtrooper had many adventures along the way, such as swimming with a crocodile in Darwin, riding a camel in Broome, and fishing at a Western Australian beach. His walking days, however, started at 5 am and involved “just looking at a white line in front of me.” At times, Loxley walked in temperatures reaching 45°C (113°F) and had lost a third of his body weight at one point in the journey. He also wore his original (if somewhat dusty and battered) stormtrooper suit for the entire adventure, going through over thirty pairs of shoes. One of his final public appearances was at an Australian Rules football match at the Melbourne Cricket Ground, en route to the finish line at his hometown of Clayton.

It is ironic that the clunky costume, which made the mission all the more challenging, also saved Loxley from a dangerous situation. While walking in northern Queensland, a snake lunged and bit him, but the stormtrooper’s trusty armor blocked any injury.^[6]

4 Unicycle Quest

While on the theme of fine Aussie expeditions, can you imagine balancing your way around Australia riding a unicycle? With no handlebars and a great deal of passion, Samuel Johnson achieved exactly that in a year-long journey from 2013 to 2014. The well-known Australian actor forged on through the heat, rain, and cold to raise funds and awareness for the Love Your Sister charity. He created the foundation in honor of his sister Connie, who was fighting cancer for a third time.

The unicycle idea came about when the siblings were laughing about it as a joke dare. However, Johnson’s determination to make it a reality saw him travel 15,995 kilometers (9,938 miles) over 364 days. He also secured the Guinness Record for the World’s Longest Unicycle Ride. Following an emotional reunion with his sister at the finish line in Melbourne, Johnson quipped that unicycles are “implausible contraptions” and “not a great way to get around.”

Connie sadly passed away from cancer in 2017, and her brother continues his dedication to the Love Your Sister charity today. Johnson received the Australian of the Year award in 2018 and went on to win first place (and the charity check) on Dancing with the Stars Australia in 2019.^[7]

3 70 Skydives for 70th Birthday

Larry Ekstrom of Michigan had no interest in a traditional 70th birthday celebration in 2012. On the day he turned seventy, he took to the skies to complete a staggering 70 consecutive skydives across 10 hours. Funds raised from this mighty achievement went to a Michigan seeing-eye dog charity, Leader Dogs for the Blind.

Riding the wind was second nature to the experienced skydiver, who returned to the plane again and again with an unfazed, “get-on-with-the-job” attitude. He also went through eight different parachutes during his all-day mission.

Milestone diving became a theme in Ekstrom’s life after he completed 60 skydives on his 60th birthday. On this occasion, he jumped to raise money for multiple sclerosis (a disease his wife suffered from). The pilot claimed that the dynamic diver “wore him out.”^[8]

2 90-Year-Old Daredevil

Betty Bromage of Abbeyfield House care home in Cheltenham, United Kingdom, does not believe in stereotypes. With lofty ambitions to celebrate her ninetieth year, the thrill-seeker completed a trio of spectacular age-defying stunts. Her adventures in 2019 raised funds for a new summerhouse and community garden at Abbeyfield House.

First up on Bromage’s to-do list was a wing walk in April 2019, her fourth at the time. Already the World’s Oldest Female Wing-Walker, this involved being secured above the wing of a vintage plane for a 15-minute joy ride over Gloustershire. The adrenaline junkie has also been known to ask the pilot to throw in a loop here and there.

Next on the agenda was shooting across the world’s fastest zip wire in Snowdonia, Wales, in May 2019, followed by rappelling down the 52-meter tall (170-foot) Eagle Tower in Cheltenham in September 2019.

After Bromage completed her rappelling challenge, she spoke of needing “a good gin and tonic” (LINK 20). She has also joked in recent times about her hope that “the wind will blow some of my wrinkles away” as she continues her daredevil antics.^[9]

1 High-Altitude Dinner Party

Extreme adventurer, Bear Grylls (of Man vs. Wild fame), is known for taking on bizarre challenges that most people would flatly decline. In 2005, this trend continued when he attended a formal dinner party at never-seen-before heights. Way beyond the safety of a skyscraper restaurant, this dinner transpired at an astounding 7.4 kilometers (4.6 miles) above the ground on a table and chairs suspended beneath a hot air balloon. Yes, that is dining in the open sky miles above Earth.

Raising money for The Prince’s Trust and The Duke of Edinburgh’s Award (LINK 24), Grylls was joined by fellow British adventurers David Hempleman-Adams and Lieutenant Commander Alan Veal. Organizer Hempleman-Adams took the trio to dizzying heights in the specially designed balloon; before Grylls and Veal climbed 12 meters (40 feet) below the balloon basket en route to dinner.

When settled (if you can call it that) at their table in formal attire, oxygen masks, and safety gear, the pair ate a three-course meal over about 20 minutes. With cutlery and plates secured to a round table and meals kept in temperature-controlled boxes, the menu featured asparagus tips, duck a l’orange, and fruit terrine. At the time, the trio broke the Guinness Record for the World’s Highest Formal Dinner Party.

As humans are not designed to hover among clouds at such high altitudes, there was the danger of hypoxia throughout this stunt—a condition that causes the body to stop functioning properly due to oxygen deficiency. It was reported that Grylls lost his oxygen mask at one point, but in his “cat with nine lives” style, no harm came to him. The dinner party team then skydived back to Earth after dessert (as any normal person would do, right?).

Following the amazing challenge, balloon operator Hempleman-Adams acknowledged that this was “the strangest record” he had ever attempted and “very dangerous.” However, he quipped about one detail he was a little disappointed about—his fellow death-defying adventurers had no leftover goodies from the dinner party for him.^[10]