The Square to Square Charity Cycle Challenges are triennial endurance cycle challenges, from the Isle of Wight, U.K. to a city in Europe, established in 2004, with the first challenge taking place in 2005:

Square to Square 2005 to Prague, Czech Republic

Square to Square 2008 to the Vatican, Italy

Square to Square 2011 to Gibraltar

Square to Square 2014 to Santandar, Spain

2017: no challenge: fallow year

2020: no challenge: coronavirus pandemic