Entry 1 sense Webster, 1913 Conestoga wagon /känˌ-əs-tōg'-ə wăg'-ən/ · Con·es·to·ga wag·on · IPA 01 A kind of large broad-wheeled wagon, usually covered, for traveling in soft soil and on prairies. 1. A kind of large broad-wheeled wagon, usually covered, for traveling in soft soil and on prairies.