Boys in kindergarten (must be 5 years old by October 31) and first grade are grouped together in in the Fox Patrol. During these first two years, they are introduced to Trail Life, learn new skills, and have fun. Due to age, Foxes may only camp overnight with a parent, guardian, or other responsible adult. 

Boys in second grade (must be 7 years old by October 31) and third grade are grouped together in the Hawk Patrol. Hawks should demonstrate an increasing awareness of the subject matter and begin to get more comfortable participating in troop activities. 

Boys in fourth grade (must be 9 years old by October 31) and fifth grade are grouped together in the Mountain Lion Patrol. Mountain Lions should demonstrate the beginnings of greater independence, ability and confidence while still requiring strong adult guidance. 

When a trailman joins a Woodlands Patrol they are given the associated patrol Branch Patch. This is the badge on which the Trailman will display the branch pins that they earn. 

Each branch has a different set of requirements consisting of a combination of Core, Elective and Hit-The-Trail steps. Once a trailman has completed these requirements they are awarded the associated Branch Pin. Bronze for Fox, silver for Hawk and Gold for Mountain Lion. Most of this work is achieved through the activities of the troop's regular Monday night meetings. To allow a Trialman to make up missed requirements, a series of Family Home Activities have also been made available.

Once a Trailman has attained all seven Branch Pins, they will be awarded the Forest Award for their respective patrol. This is the badge on which the Trialman will display the Sylvan Stars that they earn. 

Similar to the Branch Pins, Sylvan Stars are earned as the Trailman meets the set of requirements for a particular branch for the second time. It is intended that they would do this with different steps than those which earned them their Branch Pins. Bronze for Fox, silver for Hawk and Gold for Mountain Lion. Most of this work is achieved through the activities of the troop's regular Monday night meetings. To allow a Trialman to make up missed requirements, a series of Family Home Activities have also been made available. 

Navigators will take the knowledge gained in the Woodlands Trail and build upon that understanding.  They will begin to choose more of their own topics of interest to focus on through elective Trail Badges, and explore taking a leadership role within their patrol.  The Trailman will advance through the ranks details below as they achieve the requirements for each rank.  

The Recuit understands and agrees with the ideals of the Trail Life.  He takes advantage of the training and fellowship to learn and grow.

The Able Trailman is truly an able man.  He knows how to hike safely and comfortably and handle many situations.  These skills are the foundation for the Ready Trailman.

The Ready Trailman is ready for whatever happens.  He has a full set of camping skills and does his fair share of the work along with enjoying the fun.  Earning this rank in Navigators, the Trailman has the confidence and experience to teach skills to newer members and give back to the Troop.

The Troop Standard is the official way a Navigator or Adventurer Trailman displays his Trail Badges.  This is first awarded when the Trailman achieves the rank of Able Trailman.

Adventurers mature in wisdom and faith through more difficult challenges and leadership activities with Christian men walking alongside.  They plan and lead outdoor events and large projects while exercising leadership positions in the Troop, even mentoring some of the younger Trailmen.

A Journey Trailman is at the beginning of a high adventure trail, which is designed to develop their character and leadership skills.

A Horzon Trailman helps younger boys with their skills, but he also seeks to help the Troop succeed.  This award symbolizes the Trailman's ability to see the Horizon and the final place of Freedom at the end of the trail.

After earning the Freedom Award, a Trailman is referred to as a "Freedom Rangeman".  The Freedom Award is symbolic of both natural and spiritual freedom.  As a young man who will soon turn eighteen and leave their home to start a full-time job or go to college, the clear trail that was set for them by their parents is now an open range.  Attaining the Freedom Award (the highest award in Trail Life) requires a special service project that demonstrates the skills and ideals learned in the Troop.