The diversity of human language, shaped by social, cultural, and regional influences, presents significant challenges for natural language processing (NLP) systems. Existing benchmarks often overlook intra-language variations, leaving speakers of non-standard dialects underserved. To address this gap, we introduce EnDive (English Diversity), a benchmark that evaluates five widely-used large language models (LLMs) across tasks in language understanding, algorithmic reasoning, mathematics, and logic. Our framework translates Standard American English datasets into five underrepresented dialects using few-shot prompting with verified examples from native speakers, and compare these translations against rule-based methods via fluency assessments, preference tests, and semantic similarity metrics. Human evaluations confirm high translation quality, with average scores of at least 6.02/7 for faithfulness, fluency, and formality. By filtering out near-identical translations, we create a challenging dataset that reveals significant performance disparities - models consistently underperform on dialectal inputs compared to Standard American English. EnDive thus advances dialect-aware NLP by uncovering model biases and promoting more equitable language technologies.