The Simcoe County Loop Trail is an established 100 mile (160 kilometre) loop that travels through nine municipalities, reaches three major bodies of water, including Georgian Bay, Lake Simcoe and Lake Couchiching. It is primarily on off-road, multi-use rail trails.. In most cases, the trail is crushed limestone, with some sandy and/or rough sections, depending on the time of year.

--submitted by Chantal Demers

North Fiordland, South Island, New Zealand

Loop of the Hollyford Track and Pyke - Big Bay Route: Alabaster Hut to Martin's Bay (Demon Trail) to Big Bay to the Pyke Valley to Alabaster Hut. Start and finish at any point on the loop. A complete circumnavigation of Skippers Mountain Range.  100km.

--submitted by George Brill
 

This route is a magnificent, sadistic 50km tour of Pittsburgh, PA’s most unique infrastructural feature: named staircase streets. These stairs from the city’s bygone era of steel and heavy industry were a way for workers living in neighborhoods in the cliffs and hills above the 3 rivers to commute directly down and back up. Many are now closed or decrepit but remain a gritty testament to Pittsburgh’s industrial roots. In the early days of GPS navigation, drivers would apparently get directed down roads only to dead-end at a staircase.