I imported my Jekyll from Squarespace's Wordpress XML with this

import.rb

# coding: utf-8

require 'rubygems'
require 'hpricot'
require 'fileutils'
require 'safe_yaml'
require 'time'

module JekyllImport
  # This importer takes a wordpress.xml file, which can be exported from your
  # wordpress.com blog (/wp-admin/export.php).
  module WordpressDotCom
    def self.process(filename = {:source => "wordpress.xml"})
      import_count = Hash.new(0)
      doc = Hpricot::XML(File.read(filename[:source]))

      (doc/:channel/:item).each do |item|
        title = item.at(:title).inner_text.strip
        permalink_title = item.at('wp:post_name').inner_text.gsub("/","-")
        # Fallback to "prettified" title if post_name is empty (can happen)
        if permalink_title == ""
          permalink_title = sluggify(title)
        end

        if item.at('wp:post_date')
          begin
            date = Time.parse(item.at('wp:post_date').inner_text)
          rescue
            date = Time.now
          end
        else
          date = Time.now
        end

        status = item.at('wp:status').inner_text

        if status == "publish"
          published = true
        else
          published = false
        end

        type = item.at('wp:post_type').inner_text
        categories = item.search('category[@domain="category"]').map{|c| c.inner_text}.reject{|c| c == 'Uncategorized'}.uniq
        tags = item.search('category[@domain="post_tag"]').map{|t| t.inner_text}.uniq

        metas = Hash.new
        item.search("wp:postmeta").each do |meta|
          key = meta.at('wp:meta_key').inner_text
          value = meta.at('wp:meta_value').inner_text
          metas[key] = value;
        end

        name = "#{date.strftime('%Y-%m-%d')}-#{permalink_title}.html"
        header = {
          'layout' => type,
          'title' => title,
          'categories' => categories,
          'tags' => tags,
          'status' => status,
          'type' => type,
          'published' => published,
          'meta' => metas
        }

        begin
          FileUtils.mkdir_p "_#{type}s"
          File.open("_#{type}s/#{name}", "w") do |f|
            f.puts header.to_yaml
            f.puts '---'
            f.puts item.at('content:encoded').inner_text
          end
        rescue => e
          puts "Couldn't import post!"
          puts "Title: #{title}"
          puts "Name/Slug: #{name}\n"
          puts "Error: #{e.message}"
          next
        end

        import_count[type] += 1
      end

      import_count.each do |key, value|
        puts "Imported #{value} #{key}s"
      end
    end

    def self.sluggify(title)
      title.gsub(/[^[:alnum:]]+/, '-').downcase
    end
  end
end

JekyllImport::WordpressDotCom.process

rename.rb

#!/usr/bin/env ruby

require 'html2markdown'

POST_REGEX = %r{(?<year>[0-9]+)-(?<month>[0-9]+)-(?<day>[0-9]+)-(?<title>.*).html}

files = Dir.glob('*.html').select{ |f| f.match POST_REGEX }

files.each do |post|
  data = post.match(POST_REGEX)
  p = HTMLPage.new(contents: File.read(post))

  File.open(post, 'w') { |f| f.puts p.markdown }
  File.rename(post, "#{data[:year]}-#{data[:month]}-#{data[:day]}-#{data[:title]}.md")
end

Thank you!

I made a fork of this which downloads images linked to in posts from one's Squarespace account, and updates your posts to link to the downloaded copy.

Thanks!

for newbies like me, how am I supposed to run those scripts? Thanks in advance!

I would love to use this, but as a noob I don't know how. Can someone give me a rundown as to how to use this? Thanks to anyone who helps.

to use this, create new files in the root of your jekyll directory with the names and contents from above.

This was my folder structure when I ran the import:

.
├── CNAME
├── Gemfile
├── Gemfile.lock
├── Squarespace-Wordpress-Export-05-09-2017_wordpress.xml
├── _attachments
├── _config.yml
├── _pages
├── _posts
├── _site
├── about.md
├── import.rb
├── index.md
└── rename.rb

copy and paste the contents of the two above files into their respective locations.

Then, in import.rb, on line 29, change it to:

def self.process(filename = {:source => "<YOUR FILE HERE>"})

I'm no expert, but this might help some others who are trying to use this process.

Oh, and I used the fork created by @spiffytech to import images. It worked like a dream. (I hit a few broken image links, and just manually deleted them from the wordpress XML file, and re-ran the import.)

Finally, to run the whole thing, in your command line, just type ruby import.rb.

Good luck!