Stretching is commonly recommended to improve flexibility and reduce injury risk; however, its practical implementation among recreational snowboarders and alpine skiers remains inconsistent. A cross-sectional online survey was conducted during the 2024–2025 winter season. Of 403 collected responses, 391 valid questionnaires were included after data screening. The survey assessed sociodemographic characteristics, stretching perceptions, practices, perceived barriers, information sources, and supervision. Descriptive statistics and chi-square tests were used to explore associations between sport modality and generational cohorts. Although 91.3% of participants considered stretching necessary, only 39.7% reported performing stretching exercises in the previous six months. The most frequently reported barriers were lack of time (76.1%) and low motivation (54.2%). Alpine skiers attributed greater importance to stretching than snowboarders. Significant generational differences were observed in sport modality, practice volume, and information-seeking behaviour (p < 0.05), but not in stretching frequency or duration; therefore, Hypothesis 1 was not supported. Only 22.7% of participants reported receiving professional supervision. In recreational winter sports, stretching is widely valued but inconsistently practiced. Behaviour appears to be driven more by motivational and contextual factors than by generational differences in practice frequency, highlighting the need for targeted educational strategies and evidence-informed guidance.