Overseeding of tall fescue and perennial ryegrass into pre-existing stands of kentucky bluegrass is viewed as a strategy to enhance the quality and durability of turfgrass lawns. In a 3-year study, the authors investigated the winter survival and establishment of tall fescue (‘Bonsai 2000’), with or without Neotyphodium coenophialum, and perennial ryegrass (‘Palmer III’), with or without N. lolii, in the province of Quebec, Canada (≈lat., 54ºN), a region characterized by rigorous winter conditions. Grass species were overseeded in June 2003 at two different rates (90 and 180 kg·ha−1), in experimental plots from two bioclimatological conditions: Quebec City and Boucherville. Turfgrass establishment and endophyte infection were evaluated during the following two spring and fall periods. Both tall fescue and perennial ryegrass had the capacity to establish and survive winter conditions, but performed best when snow cover was thick and present throughout the winter. The proportion of overseeded plants in the turfgrass stand rarely reached 30% over the years. Although the proportion of tall fescue and perennial ryegrass plants was much reduced in the spring, some tillers survived and were able, later in the season, to compete with kentucky bluegrass as tall fescue and perennial ryegrass populations returned to initial establishment populations each summer in mixed stands. Overwinter endophyte survival was species specific, with N. lolii being able to survive the cold winter but not N. coenophialum, which had a low percent of infection. For the perennial ryegrass–N. lolii association, competition with kentucky bluegrass is a primary factor limiting the increase over time in the proportion of endophyte-infected plants in a turfgrass mixture. Seeding rates did not influence the establishment of either grass species.