Free-ranging native Dartmoor and Exmoor ponies have not only held strong cultural and environmental significance for thousands of years within their respective national parks, but their environmental benefits and naturally selected characteristics have also been acknowledged and harnessed for conservation grazing and rewilding programmes. Despite a wealth of literature regarding the welfare of sports, leisure and working horses, there is little information concerning the welfare of free-ranging and extensively grazing ponies. The present study compared the welfare of native Exmoor and Dartmoor ponies grazing on the moors in their respective national parks (n = 47) with those that have been translocated to other areas of the UK for use in conservation grazing and rewilding programmes (n = 29) using a specifically designed observational welfare assessment protocol for free-ranging ponies. The results showed a significant difference between common land and conservation grazing ponies in the scores for Body Condition Score, Water Quality and Availability, Environmental Hazards, Human Disturbance, Skin and Coat Condition and the Human Approach Test. Despite no evidence of significant welfare compromise being identified, this study emphasises the importance of year-round monitoring of welfare and the feasibility of the observational welfare protocol to be used by pony keepers and grazing managers in the future.