In this work, we present a comprehensive three-phase study to examine (1) the effectiveness of large multimodal models (LMMs) in recognizing cultural contexts; (2) the accuracy of their representations of diverse cultures; and (3) their ability to adapt content across cultural boundaries. We first introduce Dalle Street, a large-scale dataset generated by DALL-E 3 and validated by humans, containing 9,935 images of 67 countries and 10 concept classes. We reveal disparities in cultural understanding at the sub-region level with both open-weight (LLaVA) and closed-source (GPT-4V) models on Dalle Street and other existing benchmarks. Next, we assess models' deeper culture understanding by an artifact extraction task and identify over 18,000 artifacts associated with different countries. Finally, we propose a highly composable pipeline, CultureAdapt, to adapt images from culture to culture. Our findings reveal a nuanced picture of the cultural competence of LMMs, highlighting the need to develop culture-aware systems. Dataset and code are available at https://github.com/iamshnoo/crossroads
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