My boys are 8 and 14. When ds1 turned 13, I planned a bday party with a sense of ritual.
First we simply gathered & "hung out" - this was JUST family. Which, for him, was: Me, his dad, my younger son's dad & his wife (since he's sort of a stepdad and definitely family member), grandma's, grandpa's, siblings, aunts & uncles. Probably about 15 people.
I then called everyone outside to sit in a circle. I passed around a shell with smoking sage and cedar and related their historical uses as spiritual/emotional/physical purifiers and bringers of positive energy, respectively. Then, I had made a beautiful walking stick and attached some rocks, feathers, little meaningful tokens. I told everyone that this was a celebration of ds's journey out of 'childhood' and the beginning of his path toward 'manhood', that I'd pass the staff around and asked that each person relate some thoughts on ds, memories etc., and then give the gift of their wisdom/wishes for ds: sound advice, sharing powerful experiences, attributes they hope he will acquire.
It was very beautiful. I started, as his mother, and passed the staff around. Everyone spoke from their hearts; it was very powerful. Ds had tears in his eyes; so did his dad. His dad went last.
When everyone was done, I presented ds w/the staff and welcomed him onto his path of adulthood.
At his 15th birthday, I plan on including another ritual of some kind, as he will have spent two years on his path to manhood. I want to have him do some self-evaluation and get some feedback from his family members.
As far as supporting him in becoming a man, I just do what I can. I am also a single parent, but luckily his dad is involved and has him 50% of the time. I don't agree with all the ways his dad parents him, but am glad ds is given love and the attention he needs. His dad seems to be making up for lost time, and that makes me happy. I am seeing a wonderful man so my boys also get to have healthy male friends/mentors.
He is 5'11'' or so and has gotten quite muscular. I make him use that around the house and property; boys need to use their bodies (so do girls). He chops and brings in wood, stacks it on the porch and next to the woodstove. I have him dig holes to plant trees, postholes for the porch we're building on the south side of the house, pluck the turkey after he helps me kill it, move wheelbarrowfuls of dirt to the new garden site. This summer he'll be helping me fell trees and chainsawing them up. Just wait until gardening happens; moving the compost, weeding, pruning etc!
He's a computer geek by nature, so I feel it's my duty to balance out all the computer time he has w/his dad with physical and nature-based activities with me. (Kind of funny that he's so sedentary w/his dad and so active w/me- keeps me in shape!!) I forced him to get involved in a team sport and told him I'd choose one if he didn't- he chose snowboarding (we live in the mountains near Lake Tahoe). So guess what I'm doing on my weekend? Up in the snow...
A book I love: The Wonder of Boys. There's one for older boys (teens) that I can't remember the title of right now, but by the same author. Excellent book.
There's another excellent book that I love, not aimed at boys in particular, but great, short little book on wisdom/self-help (you can read volumes and volumes and not absorb it; sometimes I think simplicity is helpful). It's called The Four Agreements my Dr. Miguel Ruiz.
Most of all, check in with your inner wisdom, use the resources around you (if you don't have male friends, make some), support him is his 'maleness' but remind him that the most important thing is his 'humanness.' Know that as testosterone gets going, boys undergo a powerful physical change (like us at pms/menstruation/pregnancy/birth) and he will have specific needs to get met.
I am so blessed to have boys- they make me keep my vow to be very physically active. IMHO I think activity in nature is a #1 way to stay healthy overall. Can't get enough of it.
That and good, long, honest talks about life. Which reminds me, I need to have one w/my boys tonight; my students talked alot about the messages boys/girls get re: emotions and we had such an excellent discussion, I need to share it w/my boys!