The presence of cyclists on Spanish rural roads is ever increasing and currently frequent, and thus becoming a serious safety concern. In rural environments, the risk of a crash is higher than in rural areas. The main cause is the higher speed of motor vehicles during overtaking manoeuvres. This manoeuvre is especially challenging when cyclists ride in groups as they may change size, length, shape, and speed along their route. These variables and those related to road cross-section can influence driver behaviour when overtaking a group of cyclists. To study this, instrumented bicycles were used to ride along five road segments with different geometric and traffic characteristics. Cyclists rode individually and in groups. Overtaking was evaluated by analysing the lateral distance, the speed, and other characteristics of the manoeuvre. Wider roads presented higher lateral clearances and overtaking speeds. Narrower roads had a high opposing lane invasion but a high level of compliance with the minimum lateral clearance. A higher clearance and lower speed of overtaking vehicles was registered when cyclists rode in line. Compliance with the 1.5 m clearance depended on the group configuration, being higher when cyclists rode in line. However, overtaking cyclists riding two abreast presented more accelerative manoeuvres, especially on narrow roads.