In August of 2003, the band entered an open stage at Blistered Fingers Bluegrass Festival. This was their first festival appearance. They received recognition from the crowd and festival owners. They have since played at several area bluegrass festivals over the years, including Pemi Valley, Blistered Fingers, Ossipee Valley, BBU Springfests, BBU Fallfests, and have appeared at the Cantab Lounge, the Strange Brew Tavern and other venues. In February, 2007, they were the opening band for the Joe Val Bluegrass Festival in Framingham, MA.

Mount Monadnock is an isolated peak, 3,165-ft (965 m) high, located in southwest New Hampshire. It is a popular hiking destination, noted for its view. The peak lends its name to the geomorphic term Monadnock, an isolated mountain remnant standing above the general level of the land because of its greater resistance to erosion. It is quite popular for people to climb viewing the southern plains from the top. The group selected this name because they thought it would be good to be grounded, it is unique, and most importantly, it was the only one all members could agree upon. Through intense research, the group later learned that the term Monadnock translated from Native American means “five musicians who like to play bluegrass music for large groups of people!”