Tumor draining lymph nodes (TDLNs) represent a key component of the tumor-immunity cycle. To investigate how TDLNs impact lymphocyte infiltration into tumors, we analyzed non-tumor-invaded LNs draining “cold” vs. “hot” triple negative breast tumors. Using machine-learning based self-correlation analysis of immune gene expression, we found unbalanced intranodal regulations within TDLNCold. Two gene pairs (TBX21/GATA3-CXCR1) with opposite correlations suggested preferential priming of T helper 2 (Th2) cells by mature dendritic cells (mDCs) within TDLNCold. This was validated by multiplex immunofluorescent staining identifying shorter mDC-Th2 distances within TDLNCold. Enrichment in mast cells (MCs) with an independent validation and upregulation of IL4 in TDLNCold supported MC-induced Th2 polarization. Lastly, increased Th2/Th1, IL4/CD3D, and PDGFC/CD68 ratios were observed in paired cold tumors, connecting Th2 polarization in TDLNCold to downstream type 2 immunity within tumors. Our results reveal the novel role of MCs within TDLNs and modulating their activity may improve immune infiltration into tumors.