A relationship between chronic pain and frailty has been reported. The early detection and prevention of frailty are recommended, in part because community-dwelling older adults in a pre-frailty state may return to a healthy state. The relationship between chronic pain and pre-frailty is not known. Toward the goal of promoting a reversible return to health from pre-frailty, we investigated the relationship between chronic pain and pre-frailty among community-dwelling older adults. We assessed the frailty and chronic pain of 107 older adults who were participating in community health checks. The status of physical frailty was based on the five components described by Fried (2001): muscle weakness shown by handgrip strength, slowness of gait speed, weight loss, low physical activity, and exhaustion. Chronic pain was assessed based on pain intensity, the Pain Catastrophizing Scale (PCS), the Japanese version of the Geriatric Depression Scale-15 (GDS-15), and the Central Sensitization Inventory (CSI). The prevalence of chronic pain with pre-frailty was 40.2%. A hierarchical analysis revealed that PCS-measured helplessness (odds ratio [OR]: 0.88) and the CSI (OR: 0.87) were significant factors associated with the presence of chronic pain with pre-frailty. The prevalence of chronic pain with pre-frailty was high, and chronic pain and pre-frailty were strongly related. New intervention or prevention programs that take into account both chronic pain and pre-frailty must be created as soon as possible.