From Peekskill train to Beacon Train Station, bus to Newburgh, NY, then bus to Middletown, NY. 3 h 55 min $28. From Nelson Ave @ Main St bus to White Plains, NY then bus to Middletown, NY. 4 h 29 min $24. From Peekskill taxi to Middletown. 44 min $203. From Peekskill drive to Middletown. 44 min $4.