Charles Dickens and Mark Twain both called Hillhouse Avenue the most beautiful street in America, and its nineteenth-century mansions and the Yale president's house stretch ahead of you. Both Charles Dickens and Mark Twain described it as “the most beautiful street in America,” and you can feel why as you take in the scale and setting. The avenue is named for James Hillhouse (1754–1832) and his son James Abraham Hillhouse (1789–1841), innovators in land use who began the tree-planting that earned New Haven the nickname The Elm City and who laid out the Trumbull Plan for Yale College and the Grove Street Cemetery.
Once called Temple Avenue, it was staked out 150 feet wide by Jeremiah Day in 1792; that generous width gave room for houses set back with trees, creating the park-like effect you see imagined into the landscape. The avenue once wore a canopy of elms, though those trees were later lost to Dutch elm disease. James Abraham Hillhouse built the family mansion Highwood—later called Sachem’s Wood—up on the hill in 1828, anchoring the street’s sweep from the Green at Temple Street.
Notice the wide, tree-lined vista Jeremiah Day staked out in 1792 for the Hillhouse family.