He started his martial arts career studying Matsubayashi Shorin Ryu Karate in 1981 under Nagamine Shoshin Sensei in Naha. Pitchford Sensei studied under Nagamine Sensei for over seven years, earning his Shodan in Karate before studying under Kishaba Sensei in Yonabaru. He studied under Kishaba Sensei, a student of Hohan Soken Sensei, until Kishaba Sensei's death. Pitchford Sensei achieved the rank of Roku Dan, Sixth Degree Black Belt, in February 1998.
In 1982 Pitchford Sensei met Dr. Gordon Warner and started practicing Mugai Ryu Iaihyodo (Iaido). In 1984 he achieved shodan. Since then, Pitchford Sensei received Taikai Sho while a Godan for excellence in Iaido. Pitchford Sensei received his Rokudan in 1995 from the Nippon Iaido Federation.
While still a Godan he was awarded two scrolls (something usually only given after one achieves Rokudan) from the soke (headmaster) of Mugai Ryu. These scrolls are a traditional license and a scroll of strategy awarded when a certain level of skill is achieved. This license is from the style, in this case Mugai Ryu, and independent of any rank award from the federation. The next level of scroll is known as Menkyo Kaiden and is the scroll of full transmission of the style.
Pitchford Sensei also was awarded the rank of Yonmokuroku by Shitama Sensei, the soke of Sosuishitsu Ryu Kumiuchi Koshi no Mawari, in 1999. This rank is the equivalent of a Yondan. Sosuishitsu Ryu is a style of jujitsu (Kumiuchi) and Iai (Koshi no Mawari) dating back over 350 years. Pitchford Sensei is a student of Usuki Sensei; the head of the Tokyo dojo of Sosuishitsu Ryu.
Haga Dojo practices Kendo as a martial art, rather than sport. This old dojo practices Shinto Munen Ryu Kenjutsu and Hasegawa Eishin Ryu Iaido in addition to Kendo practice. Pitchford Sensei has been a member of this dojo for the past 7 years. No rank is given in this dojo.
Pitchford Sensei is also a student of Yonehara Sensei the soke of Sekiguchi Ryu. He has been studying this style of Iai for 9 years. Sekiguchi Ryu is a style of from Kumamoto Prefecture. Members of Sekiguchi Ryu also practice Hyoho Niten Ichi Ryu Kenjutsu (Miyamoto Musashi's style) and preserve the teachings of Aoki Sensei.
In addition to his martial arts training Pitchford Sensei studied Japanese Armor under Sasama Sensei, the foremost authority on the construction and authentication of Japanese armor in the world. The National Museum in Tokyo calls Sasama Sensei "The Armor God." Pitchford Sensei studied under Sasama Sensei for 4 years