In 1963, President John F. Kennedy asked his military to prove they were in fine physical condition by marching 50 miles. (JFK was simply following a suggestion made by Teddy Roosvelt many years before). However, this was the cold war era and proof of strength and stamina served a useful purpose.
Before the military ever had a chance to test their troops, Robert F. Kennedy, the President’s brother and Attorney General, walked 50 miles from Great Falls, Maryland to Harpers Ferry, West Virginia on the C&O Canal towpath along the Potomac. He instantly set a high bar for fitness. That walk encouraged thousands of others as the public began to walk distances they thought impossible. JFK’s military order had turned into a public fad for walking long distances. Many ordinary individuals took the challenge upon themselves to test how fit they were. This was a publicity mistake turned into a fortunate event that helped boost the public’s attention to physical fitness. — 50-Mile Kennedy Walk
Does this sound like fun? A group has started running an annual re-enactment of Bobby Kennedy’s walk — now with trail support and options for people who can’t cover the full distance (yet!). You can get more information about their event and preparation for this kind of hike at their website. The Kennedy March has appealed to people in the UK and Europe as well, with various events organized far from Maryland.
I’ll be honest, I don’t see myself doing 50 miles on the C&O Canal towpath in February, but the towpath is open all year, and is a wonderful place for hikes, walks, and bike rides. There are lots of entry points near the various towns along the route, some of which (like Kennedy’s stop, Harpers Ferry) are delightful destinations on their own.