In 2003, along with Grants Pass Tourism, Jeffery created the highly successful event, Art Along the Rogue Street Painting and Music Festival. Since the beginning, Jeffery has designed all the posters, print ads and t-shirts, created and placed all broadcast advertising, hired all the bands and street painters, emceed the weekend and performed a few shows with his bands Siskiyou Summit and Generation Jones.
Since 2009, Jeffery has managed A Taste of Ashland for the Ashland Gallery Association. This premiere art, food and wine tasting event is the major fund-raiser for the Association. Jeffery have created the posters, print advertising, Food & Beverage Guide, sold advertising and sponsorships, coordinated all of the galleries, wineries, and restaurants, plus ticket sales, raffle and People’s Choice Awards for the event that attracts around 900 tasters for the weekend.
In 2012, Jeffery was hired to create a new event for the Ashland Art Center called Art Inspires Ashland. This TED-like event brought three world-renowned artists to Ashland to give workshops and inspirational presentations. It included an Artist Meet & Greet and a Gala Dinner as part of the fund-raiser.
In 2010, Jeffery created the Phoenix Phestival in Phoenix, Oregon. This community-building event included afood and wine-tasting, craft vendors, musical stage performances, and a Guinness World Record for the World’s Longest Taco – 177 feet long. The taco, once measured, was consumed by the Phestival attendees.