In 1999, the Bergs planted seven acres of mostly Pinot Noir on the 20-acre property near Yamhill in the Yamhill-Carlton District of the Willamette Valley. Chuck and Dian built a small house on the vineyard, and Chris lived in Portland with his wife, Hilary, also a Jayhawk.
By 2005 vintage Roots Vineyard produced 350 cases. In this same year, Chris also decided to purchase winegrapes from Cherry Grove Vineyard, Apolloni Vineyard (near Banks) and Leroy Vineyard (just outside of Hillsboro). In all, 550 cases were produced for the three labels: Roots, Racine and Klee.