American elderberry (Sambucus canadensis) is a plant native to North America with anthocyanin-rich fruits. Our objective was to investigate the effects of cultivar and ripeness on the phytochemical characteristics of its fruits and the corresponding color performance. Cultivars ‘Adams’, ‘Johns’, ‘Nova’, ‘Wyldewood’, and ‘York’ were examined for their◦Brix, pH, anthocyanin (pH-differential method), and phenolic content (Folin-Ciocalteau method). Extract composition were analyzed by uHPLC-PDA-MS/MS. Color and spectra were determined using a plate reader. All characteristics evaluated were significantly affected by ripeness and cultivar, except for◦Brix and total phenolic content, which did not vary significantly among cultivars. Most anthocyanins (63–72%) were acylated with p-coumaric acid, with cyanidin-3-(trans)-coumaroylsambubioside-5-glucoside the most predominant. The proportion of acylated anthocyanins was the only characteristic evaluated that decreased during ripening (from 80 to 70%). Extract from fully-ripened fruits exhibited red (lvis-max ~520 nm) and blue hues (lvis-max ~600 nm) at acidic and alkaline pH, respectively. Extracts from half-ripe fruit rendered yellowish tones and overall dull color. C-18 semi-purified extracts displayed higher color saturation (smaller L* and larger C*ab) than crude extracts. The vibrant and broad color expression of fully-ripened fruit extract, especially after C-18 purification, suggests this North American native plant as a promising natural colorant source.