Santa’s arrival in Middlebury, downtown Middlebury, Saturday December 3rd starting at 9:45 am. Kick the holiday season off with a fun-filled morning in Middlebury. Welcome Santa as he arrives via fire truck, over the Cross Street Bridge and up Main Street, going around twice to give everyone time to see him. Then, enjoy a visit with the right jolly old elf himself at the Middlebury Community House from 10 a.m.-12:30 p.m. Families can take an old-fashioned horse drawn wagon ride through Middlebury from 10 a.m.-noon. Free.