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Both Upland and the nearby unincorporated San Antonio Heights to the north are home to a wealth of historic properties that sprang up in the late 19th and early 20th centuries. Many are open for tours; consult the local chamber of commerce for more information.
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.