Does running 20+ miles of technical single track and soloing classic rock routes sound fun? If so, then this route is for you. This route was not my brainchild, but something I saw on Mountain Project that Shawn S. envisioned, but never attempted. Essentially this route connects 8 different traprock cliffs along the Metacomet Trail. The route is likely around 23 miles (mileage will vary depending on which connector trails/roads you take). Here are the details with route names on each cliff:

Rattlesnake Mnt (Green Goddess 5.8)

Pinnacle Rock (Emerald City 5.8)

The Paint Creek Trail is an 8.9 mile trail located in northeast Oakland County. It was the first Non-Motorized Rail-to-Trail in the State of Michigan, as it was converted to a trail from the former Penn Central Railroad. Open to the public since 1983, the Paint Creek Trail receives over 100,000 visitors annually. The non-motorized Trail is 8 feet wide, and traverses through Rochester, Rochester Hills, Oakland Township, Orion Township and the Village of Lake Orion.

Monadnock to Wachusett ties together two of the most popular hiking destinations in the Boston area. In addition to the two main summits, you summit a smaller peak, Gap Mountain, and traverse a series of trails (Pumpelly, White Arrow, Royce, Midstate, and Old Indian), fire roads, and bike paths (Monadnock Recreation Rail Trail, North Central Bike Path, and Heywood Branch Bike Path) as you go from one mountain to the other.  The route is about 75% off road, goes through the towns of Jaffrey, Fitzwilliam, Winchedon, Gardner, Westminster, and Princeton.