The Mediterranean diet (MD) is one of the most healthful dietary patterns, beneficial for humans and the environment. However, the MD has recently exhibited a declining trend, especially in younger and less affluent people. This study investigated the association between socioeconomic indicators and adherence to the MD in 4671 adult subjects from Dalmatia, Croatia (age range 18–98 years; 61.9% were women). Additionally, in the follow-up we examined the change in adherence to the MD and in BMI (subsample, N = 1342; 62.5% were women; mean follow-up time of 5.8 years). The adherence to the MD was based on the Mediterranean Diet Serving Score (range 0–24 points, cut-off value ≥ 14 points), with a prevalence in the overall sample of 28.5%. Higher odds of adherence to the MD were recorded in women, older subjects, and those with higher level of objective material status, while it was less likely in the period after economic crisis of 2007–2008. Additionally, we detected no change in adherence to the MD in the follow-up subsample (−8.5%, p = 0.056), but there was an increase in BMI (+6.5%, p < 0.001). We recorded an increase in adherence for nuts (+127.5%), sweets (+112.6%), red meat (+56.4%), and wine (+50.0%), unlike the reduction in adherence for vegetables (−35.1%), fish (−23.4%), white meat (−11.6%), cereals (−10.9%), and dairy products (−9.6%). Similar results were obtained across all quartiles of objective material status. Over time, the absolute change in the MD score was positively associated with female gender, age, higher education, and moderate physical activity, but it was negatively associated with adherence to the MD at baseline. BMI change was positively associated with female gender, and negatively with initial BMI, initial adherence to the MD, and MD change. Our findings point towards a less than ideal adherence to the MD in the general population of southern Croatia, and identify important characteristics associated with adherence change over time, informing necessary interventions aimed at increasing MD uptake.