Two pasture systems (cool and warm season grass species) with enhanced in-field and landscape level species diversity were analyzed for forage quality characteristics across the grazing season at the West Central Outreach and Research Center organic dairy in Morris, Minnesota, for 2 years. System 1 was a diverse-mixture of cool season grasses and legumes (perennial ryegrass, white clover, red clover, chicory, orchardgrass, meadow bromegrass, alfalfa, meadow fescue). System 2 was a combination of perennial polycultures and annual-warm season grasses (BMR sorghum-sudangrass and teff grass). Grazing of lactating cows was initiated when forages were 20–30 cm tall and strip size was adjusted to leave 7 to 13 cm of refusals. Random samples of pasture forage were sampled every other day when a group of cows moved to a new paddock. Pasture clippings were randomly collected in a 0.76-m² square of pasture. Forage samples were sent to Rock River Laboratory, Inc., Watertown, WI and were analyzed with NIR spectrophotometry for DM, CP, and total-tract NDF digestibility (TTNDFD). Data were analyzed using the MIXED procedure of SAS. Independent variables for analyses were the fixed effects of system [cool (1) or cool-warm (2)], month (May to October), forage (grass pasture, turnips, BMR sorghum-sudangrass or teff), year (2013 or 2014) and their interactions, and date of harvest was a random variable. The DM averaged 20.7% and 21.2% for systems 1 and 2, respectively (P = 0.75). The CP was 21.2% and 18.3% for systems 1 and 2, respectively (P < 0.05). The CP for system 1 averaged 19.9% in 2013 and 22.5% in 2014 (P < 0.01). The CP for system 2 averaged 16.1% in 2013 and 20.4% in 2014 (P < 0.01). The TTNDFD averaged 69.9% and 53.1% for system 1 and system 2, respectively (P < 0.01). The TTNDFD was 78.1% in 2013 and 61.7% in 2014 for cool-season grasses, and 59.8% in 2013 and 46.4% in 2014 for warm season grasses (P < 0.0001). In summary, CP and TTNDFD were greater in cool-season pasture systems; however, DM did not differ between pasture systems. Yearly effects and weather may affect forage quality in both pasture production systems.