Script I wrote and used to migrate my SquareSpace blog to Octopress.

squarespace_to_octopress.rb

#!/bin/env ruby

require 'rubygems'
require 'fileutils'
require 'pathname'
require 'pp'
require 'date'
require 'uri'
require 'html2markdown'
 
# usage: ruby squarespace_to_octopress.rb squarespace_export.txt octopress _posts directory
# squarespace_export.txt is a file from JournalPage -> Configuration -> Export Data in Squarespace.
# octopress _posts directory is your octopress/source/_posts directory
# crawled site root directory is an optional argument that specifies a directory on local disk that is a crawled
#                             mirror of your site - used to extracting tags
 
if (ARGV.length != 2 && ARGV.length != 3) 
  $stderr.puts "Usage: #{$0} <squarespace_export.txt> <octopress _posts directory> [ crawled site root directory ]"
  exit 2
end



@posts = []

def reset_state
  @current = {:date => "", :title => "", :body => "", :markdown => "", :author => "", :allow_comments => false, :published => false, :categories => []}
  
  @inBody = false
  @inHeader = true #The file start with the first header
  @inComments = false
end

File.open(ARGV[0]) do |f|
  reset_state

  f.each_line do |line|
    if line.strip == "--------"
      @posts.push @current if (@current[:title] != "")
      reset_state
    elsif @inBody
      if line.strip == "-----"
        p = HTMLPage.new :contents => @current[:body]
        @current[:markdown]=p.markdown
        @inBody = false
      else
        @current[:body] += line
      end
    elsif @inHeader
      if line.strip == "-----"
        @inHeader = false
      elsif (line =~ /^AUTHOR:/) 
        @current[:author] = line.strip.gsub(/^AUTHOR: /,'')
      elsif (line =~ /^TITLE:/) 
        @current[:title] = line.strip.gsub(/^TITLE: /,'')
      elsif (line =~ /^DATE:/) 
        @current[:date] = Date.strptime line.strip.gsub(/^DATE: /,'') , '%m/%d/%Y %I:%M:%S %p'
      elsif (line =~ /^CATEGORY:/) 
        @current[:categories].push line.strip.gsub(/^CATEGORY: /,'')
      elsif (line =~ /^ALLOW COMMENTS:/) 
        @current[:allow_comments] = (line.strip.gsub(/^ALLOW COMMENTS: /,'') == "1")
      elsif (line =~ /^STATUS:/) 
        @current[:published] = (line.strip.gsub(/^STATUS: /,'') == "Publish")
      elsif line.strip == "-----"
          @inHeader = false
      end
    elsif @inComments
      if line.strip == "-----"
        @inComments = false
      else
        $stderr.puts "Warning: Skipping unsupported comment"
      end
    else
      if line.strip == "BODY:"
        @inBody = true
      elsif line.strip == "COMMENT:"
          @inComments = true
      end
    end
  end
  @posts.push @current if (@current[:title] != "")
end

count=0

@posts.each { |p|
  # .gsub(':','%3a')
  # http://www.escortmissions.com/blog/2012/7/7/new-work-in-progress-million-words-multiplayer-crossword-gam.html
  # http://www.escortmissions.com/blog/2012/6/10/my-top-5-factors-for-ios-contracting-success.html
  sqsp_title=p[:title].downcase.gsub(/[^a-z0-9\- ]/,'').gsub(/ /,'-').gsub(/--*/,'-')[ 0 .. 59 ].sub(/-$/,'')
  sqsp_slug="#{p[:date].strftime('%Y/%-m/%-d')}/#{sqsp_title}.html"
  if (ARGV.length == 3) 
    crawled_file_name = "#{ARGV[2]}/blog/#{sqsp_slug}"
    pn = Pathname.new(crawled_file_name)
    if (!pn.exist?)
      ## try the previous day - I have a tendency to post aroud midnight
      previous_day = (p[:date]-1)
      previous_day_crawled_file_name = "#{ARGV[2]}/blog/#{previous_day.strftime('%Y/%-m/%-d')}/#{sqsp_title}.html"
      pn_prev = Pathname.new(previous_day_crawled_file_name)
      if (pn_prev.exist?)
        sqsp_slug="#{previous_day.strftime('%Y/%-m/%-d')}/#{sqsp_title}.html"
        pn=pn_prev
        crawled_file_name=previous_day_crawled_file_name
      end
    end
    if (!pn.exist?)
      $stderr.puts "Warning, Couldn't find file #{crawled_file_name}"
    end
  end
  filename = sqsp_title.sub(/$/,'.markdown').sub(/^/,p[:date].strftime('%Y-%m-%d-'))
  
  File.open("#{ARGV[1]}/#{filename}", 'w') { |file| 
    file.puts("---")
    file.puts("layout: post")
    file.puts("title: #{p[:title].gsub(':','&#58;')}")
    if (p[:date].is_a?(Date))
      file.puts("date: #{p[:date].strftime('%Y-%m-%d %H:%M')}")
    else
      $stderr.puts "Bad date: #{p[:date]} on post #{count}:#{filename}"
    end
    file.puts("permalink: /blog/#{sqsp_slug}")
    file.puts("comments: #{p[:allow_comments]}")
    if (p[:categories].length > 0)
      file.puts("categories: #{p[:categories]}")
    end
    if (crawled_file_name) 
      if (pn.exist?)
        crawled_page = Nokogiri::HTML(open(crawled_file_name))
        tags=[]
        crawled_page.css("span[class='tag-element']").each {|tag|
          tags.push tag.text.strip
        }
        if (tags.length>0) 
          file.puts("tags: #{tags}")
        end
      end
    end
    file.puts("---")
    file.puts(p[:markdown])
  }
  count += 1;
}