Today, I made an Applescript to make DayOne entries from a folder with images. It uses EXIFtool to extract date and time from the meta information stored inside the image. The code was heavily borrowed from this posting on making DayOne entries from Aperture. Somehow, that script did not work for some images.
If you want the image file to be deleted, uncomment the line at the end of the script
## start of code ##
# Create Dayone entries from folder with JPEGs
# based on http://d.pr/n/a2MQ
# Can only be used for http://dayoneapp.com
# in combination with the associated CLI tools
# change the path to your export folder
set a_Folder to "/Users/username/Desktop/export/"
set a_folder_list to list folder a_Folder without invisibles
repeat with x from 1 to count of a_folder_list
set the_file to quoted form of (a_Folder & item x of a_folder_list)
set shell_command to "exiftool -exif:DateTimeOriginal " & the_file
#display dialog shell_command
set a_date to do shell script shell_command
set theYear to word 4 of a_date as integer
set theMonth to word 5 of a_date
set theDay to word 6 of a_date
set theHour to word 7 of a_date
set theMin to word 8 of a_date
set theSec to word 9 of a_date
set theDate to theMonth & "/" & theDay & "/" & theYear as string
#display dialog theMin
set theAP to "AM"
if theMin is less than 10 then
set theMin to "0" & theMin
end if
if theHour is greater than 12 then
set theAP to "PM"
set theHour to theHour - 12
end if
set theTime to theHour & ":" & theMin & " " & theAP as string
set theDateTime to "\"" & theDate & " " & theTime & "\""
set theScript to "echo \"\" | /usr/local/bin/dayone -p=" & the_File & " -d=" & theDateTime & " new" as string
set theEntry to do shell script theScript
set theLength to the length of theEntry
set theStart to theLength - 39
set theEnd to theLength - 8
set theUDID to text theStart thru theEnd of theEntry
tell application "Safari"
set the URL of the front document to "dayone://edit?entryId=" & theUDID
end tell
# uncomment the line below to enable deletion of the image file
# do shell script "rm " & the_File
end repeat
## end of code ##