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Historic Route 66, today's Foothill Boulevard, passed through Upland en route to San Bernardino or Santa Monica. Today, the stretch contains an interesting mix of old and new and is seeing a revival with new businesses and street improvements.
One of many Madonna of the Trail statues that commemorate American pioneer women, the one in Upland is located at the busy intersection of historic route 66 and Euclid Avenue. The monument was dedicated in 1929 and contains inscriptions that honors Jedediah Smith's 1826 crossing of the area in search of a westward-flowing river.