1. Most migratory songbirds travel between their breeding areas and wintering grounds through a series of nocturnal flights. The timing of their departures defines the potential flight duration and thus the distance covered during a migratory night. Yet, migratory songbirds show substantial variation in their nocturnal departure timing. 2. With this study we aim to assess whether the respective challenges of the migration route, namely its distance and nature, help to explain this variation. 3. At a stopover site, we caught Northern Wheatears (Oenanthe oenanthe) of two subspecies that differ in distance and nature of their onward migration route in spring, but not in autumn. We determined the start of their nocturnal migratory restlessness during short-term captivity, and radio-tracked their nocturnal departure timing after release in both migration seasons. 4. Northern Wheatears started their nocturnal migratory restlessness earlier when facing a long remaining migration distance and an extended sea barrier in spring. Individual departure directions generally affected the nocturnal departure timing with early departures being directed towards the respective migratory destination. In spring, this pattern was predominantly found in birds carrying relatively large fuel stores, but was absent in lean birds. At the same time, birds facing a short remaining migration distance and no extended sea barrier strongly reacted to relatively large fuel stores by an early start of nocturnal migratory behavior (migratory restlessness and departure timing), whereas this reaction was not found in birds facing a long remaining migration distance and sea barrier. 5. These results suggest that the basic diel schedule of birds’ migratory activity is adapted to the onward migration route. Further they suggest that birds adjust their behavioral response, i.e. start of nocturnal migratory behavior, to fuel stores in relation to their impending migratory challenges. This is a substantial step in understanding variation of nocturnal departure timing and its adjustments in migratory songbirds. Further, it emphasizes the importance of interpreting birds’ nocturnal migratory behavior in the respective ecological context.