Chronic headache is common in the elderly, but there is little specific research on the impact on quality of life of headache and beliefs about pain in this age group. This study investigated the influence of headache type as well as headache frequency (≥15 headache days/month vs. <15 headache days/month) on quality of life and determined the relationships between elder’s well-being, pain beliefs and related headache features including commonly reported neck pain. 118 headache subjects and 44 non-headache controls, aged 60–75 years, were recruited from the community. Subjects completed a headache questionnaire for classification purposes, the SF-36, the Geriatric Depression Scale-short form (GDS-S), the Survey of Pain Attitudes (SOPA-35) and the Neck Disability Index (NDI). The results revealed that elders with headache compared to the control group scored lower on most SF-36 domains, higher on the GDS-S (p < 0.05) and comparably on the SOPA-35 (p > 0.05), noting that the GDS score was below the threshold value for depression. These measures were not different between the headache types but were influenced by headache frequency. Subjects with headaches ≥15 days/month scored lowest on SF-36 domains and highest on GDS-S questionnaire compared to those with headache <15 days/month and controls (all p < 0.05). The mean NDI score in the headache subjects indicated the presence of mild to moderate neck pain and disability. There were no strong relationships between well-being and headache frequency, intensity and length of headache history. The NDI score had the greatest influence on physical well-being and GDS-S score on mental well-being (p < 0.001). The results suggest that frequency of headache has an impact on health-related quality of life in elders. Notably, the level of neck pain and disability is an important factor influencing well-being and may warrant attention in the management of elders with chronic headache.