When Cleveland Park was first developed around the turn of the 20th century, it was known as “Connecticut Avenue Highlands”. You can just make out a billboard advertising the new development in this photo. The billboard is near the current site of the Uptown Theater and the houses in the background are on Newark Street. It’s instructive to remember as you drive through Washington’s exurbs that a century ago Cleveland Park was one of those areas where rural land was being cleared for new subdivisions.
Note the multimodal transportation: a trolley car and a horse-drawn carriage, and cars, too, for the buyers the developers were really courting! Development of the area was made possible by the completion of the Connecticut Avenue bridge over Rock Creek Park, which allowed the extension of a trolley line from downtown to Chevy Chase.
Some background on the development of Connecticut Avenue Highlands is available in this 2005 Intowner article by Paul K. Williams (pdf). Thanks to CPHS member Laine Shakerdge for the copies of these wonderful pics. Do you have old pictures or stories to tell of Cleveland Park in days of yore? Drop us a line. We’d love to feature your stories here.