Background/Objectives: The Mediterranean Diet (MD) is a lifestyle offering numerous health benefits. Nevertheless, the adherence to the MD is moderate even in Mediterranean countries. While sociodemographic factors influence MD adherence, additional impacts occurred due to the COVID-19 pandemic. This cross-sectional longitudinal study with three cohorts of Portuguese adults analyzes MD adherence before, during, and after the COVID-19 pandemic, and explores the effect of sociodemographic variables. Methods: Sociodemographic factors, lifestyle habits, and MD adherence were assessed in the years 2019, 2021, and 2024 with an online self-filled questionnaire. MD adherence was measured with the Mediterranean Diet Adherence Screener (MEDAS). Results: MEDAS score increased significantly (p < 0.05) from 2019 to 2021 (6.2 ± 0.7 to 7.7 ± 0.1), followed by a significant (p < 0.05) decrease in 2024 (7.2 ± 0.1) relative to 2019, which was more pronounced in participants with higher income. Accordingly, a trend in healthier food choices was observed followed by a decline in 2024. Of note is the significant increase in red meat consumption (p < 0.05) in 2024 relative to 2021. Respondents who consumed more red meat were mostly men, employed, or in a stable relationship. Most respondents practiced sport “Never or occasionally” in 2019 and 2021 (59.4 and 55.2%, respectively); in 2024, this category was significantly (p < 0.05) reduced (40.9%); men or higher-income participants were more likely to meet the recommended activity levels. Conclusions: This study reveals that the improvements in MD lifestyle during the pandemic were not sustained in 2024, as healthier habits formed during confinement were not fully integrated into long-term behavior. These findings strengthen the need for targeted public health interventions to promote the MD.