The safety of existing bridges may be assessed using data from monitoring. The fatigue damage induced during observation period is extrapolated to the total service duration of a structure, and the reserve capacity is estimated. However, due to the randomness of road traffic, there exists a risk of underestimation of damage using a short-term monitoring campaign. This paper analyses the influence of monitoring duration on the obtained results using datasets collected during two long-term (>3 years) dynamic monitoring campaigns. Two road bridges with different nature of traffic are considered: (a) a heavily loaded two-lane highway viaduct and (b) a road viaduct with a bi-directional traffic. The deck slabs of both bridges are monitored using strain gauges installed on reinforcement bars. The daily, seasonal, year-to-year and COVID-19 lockdown-induced variations of measured action effects and calculated equivalent fatigue damage are discussed. The resampling method is used for simulation of possible short-term monitoring campaigns during the period considered, with different order of heavy vehicles arriving. The Extreme Value Theory serves to answer what is the required monitoring duration for reliable results. Possible ways of considering the monitoring duration in the fatigue damage calculation are discussed, and the methodology for damage extrapolation proposed.