Improving fruit quality is an important but challenging breeding goal in winter squash. Squash breeding in general is resource-intensive, especially in terms of space, and the biology of squash makes it difficult to practice selection on both parents. These restrictions translate to smaller breeding populations and limited use of greenhouse generations, which in turn, limit genetic gain per breeding cycle and increases cycle length. Genomic selection is a promising technology for improving breeding efficiency; yet, few studies have explored its use in horticultural crops. We present results demonstrating the predictive ability of whole-genome models for fruit quality traits. Predictive abilities for quality traits were low to moderate, but sufficient for implementation. To test the use of genomic selection for improving fruit quality, we conducted three rounds of genomic recurrent selection in a butternut squash (Cucurbita moschata) population. Selections were based on a fruit quality index derived from a multi-trait genomic selection model. Remnant seed from selected populations was used to assess realized gain from selection. Analysis revealed significant improvement in fruit quality index value and changes in correlated traits. This study is one of the first empirical studies to evaluate gain from a multi-trait genomic selection model in a resource-limited horticultural crop.