The Times has a great article about circumnavigating the city. By foot.
The idea is simple: walking the circumference of Manhattan in one go. The writer mentions 12 hours and band-aids. Walking for 12 hours sounds like a doable endurance challenge and it’s not nearly as bad as trying to become part of the Adirondack Winter Forty-Sixers.
Who’s with me to do this? My only concerns are that Winter is fast approaching and you would need to dedicate one full day (a Saturday) of your weekend to do it.