Look for Upland Sandpipers in open, expansive grasslands, prairies, hayfields, and pastures across North America during the breeding season. During migration and in their South American wintering grounds (e.g., Argentina, Uruguay, southern Brazil), they can be found in similar open grassy areas. They often perch conspicuously on fence posts, telephone poles, or tall vegetation.

Listen for its ethereal, flute-like 'wolf whistle' call, often a series of rising and falling notes, which is unmistakable and frequently given during its characteristic aerial display flights or from a prominent perch. Visually, look for its distinctive silhouette: long neck, small head, and an overall 'hunched' appearance when perched. They can be shy and well-camouflaged, so patience is key.

Upland Sandpipers are most active during daylight hours. The breeding season in North America spans from late spring to early summer, when their vocalizations and display flights are most prominent. Spring migration typically occurs from April to May, and fall migration from late July to September, offering opportunities to spot them along their migratory routes.