Flowering time is an important trait in wheat breeding as it affects adaptation and yield potential. In the southeastern United States, where winters are characterized by variable periods of warm weather that may be followed by cold, wheat cultivars that flower too early have an increased risk of frost damage. In contrast, cultivars that flower too late have increased risk of high temperature stress and water deficit, which can restrict grain formation and consequently reduce yield. Multiple mapping studies involving early flowering eastern soft red winter (SRW) wheat cultivars have identified QTL for heading date associated with variation at the VRN1 and PPD1 loci. These include a winter allele of Vrn-B1 having a 36 bp intron one deletion associated with early flowering after shorter periods of cold treatment. Evaluation of diverse winter wheat germplasm determined this allele was rare in global germplasm but was detected in the North American landrace Purplestraw and is common in modern southeastern wheat cultivars. In addition, Purplestraw possessed the globally rare Ppd-A1a.1 allele having a 1,085 bp deletion in the critical upstream region that is present in approximately 40% of contemporary eastern wheats. Recent mapping has identified alleles of other genes in the flowering pathway important to regional adaptation. Evaluation of genotypic and phenotypic data from multiple years of collaborative SRW wheat yield trails revealed winter alleles of Vrn-A1 and Vrn-B1 requiring shorter periods of cold to potentiate flowering in combination with insensitive PPD1 alleles provide a grain yield advantage at southern locations. In the Mid-Atlantic region, longer vernalization requirement combined with the Ppd-D1a allele was desirable. Generally, genotypes having reduced vernalization requirement in combination with the less potent Ppd-A1a and Ppd-B1a insensitive alleles performed well across environments, suggesting these gene combinations may be involved in broad adaptation. Our results demonstrate that VRN1 and PPD1 alleles of varying strength deployed in combination with genes of smaller effect allow fine tuning of flowering time in diverse winter wheat growing environments.