Richard's Pipits prefer open, short-grass habitats such as steppes, grasslands, cultivated fields, and coastal plains. During migration, they can be found in similar open areas, including shorelines and sparse vegetation, making them accessible to birdwatchers in a wide range of geographical locations.

Spotting a Richard's Pipit often involves listening for its distinctive, explosive 'schrip' call, especially when flushed from cover. It typically walks or runs on the ground with an upright stance, constantly flicking its tail. When disturbed, it flies up high before descending in an undulating flight. Its streaky brown plumage provides excellent camouflage against dry grass, so patience and careful observation of ground-level movement are key.

This species is most active during daylight hours, foraging for insects. In its breeding range, it is present from May to July. For birdwatchers outside the breeding grounds, the best time to observe Richard's Pipits is during their autumn migration (typically late September to November) and less commonly during spring migration (March to May), when they might appear in unexpected locations across Europe and other regions outside their primary migratory routes.