Eleven new species of Diptera are reported from the middle Eocene Kishenehn Formation in northwestern Montana, USA. Belonging to 10 families, four of which (Apsilocephalidae, Keroplatidae, Opetiidae and Scenopinidae) are new to the formation, they expand the record of Kishenehn Formation Diptera to 25 families and 38 fossil species. Taxa are as follows with significance noted: Palaeoapsilocephala kishenehnensis Hauser and Greenwalt, gen. et sp. n. (Apsilocephalidae); Dilophus idanos Fitzgerald and Greenwalt, sp. n. (Bibionidae), the first fossil of the genus in the Nearctic and the oldest known fossil imago of the genus; Tmemophlebia carolinae Evenhuis and Greenwalt, sp. n. (Bombyliidae), the first fossil of the genus and the oldest fossil of the subfamily Poecilognathini; Microphorella fragilis Cumming and Greenwalt, sp. n. (Dolichopodidae), the first fossil of the genus and the first fossil parathalassiine from the Nearctic; Hoplocyrtoma eocenica Sinclair and Greenwalt, sp. n. (Hybotidae), the first fossil of the genus; Macrocera apithanos Kerr and Greenwalt, sp. n. (Keroplatidae), the first fossil species of the genus from the Nearctic; Azana akarenos Kerr and Greenwalt, sp. n. (Mycetophilidae), the first fossil of the genus in the Nearctic and the oldest known fossil of the genus; Opetia americana Amorim and Greenwalt, sp. n. (Opetiidae), the first definitive fossil of the genus and the first of its family from the Nearctic; (Psectrosciara makrochaites Amorim and Greenwalt, sp. n. and P. crassieton Amorim and Greenwalt, sp. n. (Scatopsidae); Brevitrichia messogenes Greenwalt and Winterton, sp. n. (Scenopinidae), the first fossil of the genus and, if Proratites simplex Grimaldi and Cumming, 1999 proves not to be a scenopinid, the oldest representative of the family. The bibionid species Dilophus magnus DĂŒrrenfeldt, 1968 was re-examined and designated as Bibionidae incertae sedis. In addition, two species previously assigned to Apsilocephala, Psilocephala pusilla Hennig, 1967, and Rueppellia vagabunda Cockerell, 1927, are reassigned to the new genus as Palaeoapsilocephala.