It is significant for historical association, for architecture, and for information potential (the latter for possible archeological investigation of the Academy Hill Green area of a 17th-century fort.[2]
Selected significant elements in the district include:
Capt. David Judson House, 967 Academy Hill, built 1723, which in 1978 was a museum run by the Stratford Historical Society
William A. Booth House, 956 Broad Street, built 1857, designed by architect Leopold Eidlitz in "Swiss Chalet" style[2]: 9
Lieut. William Thompson House, 904 East Broadway, a saltbox from 1762[2]: 11
Old Episcopal burying ground
First Congregational Church, 2301 Main Street (accompanying photograph #7)
The district also includes dozens of other historical houses including the Stratford Shakespeare American Theatre, a singular 1500 seat venue where currently popular American Hollywood actors have performed.