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I'm building a site for an art gallery, in the old cms has 20 years worth of exhibitions. The old system is custom built and is not based on anything readymade, so finding an importer plugin made for that is out of a question.

Any idea how to proceed?

Big thanks!

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I'd dump part of the database and see how the posts/pages/ titles, date and other meta is arranged and compare it to Wordpress's DB structure.

See http://codex.wordpress.org/Database_Description and http://codex.wordpress.org/Importing_Content for existing importers.

Decide what you really need to import and what needs to be generated that is specific to WP.
It's not going to be an easy move.

You may be able to work with the text database dump with grep and other text tools to manipulate it into an import file.

You can also export the database in CSV using phpmyadmin, work with the cells/tables, and try http://wordpress.org/extend/plugins/csv-importer/

One other alternative: does the old CMS have an RSS feed? That's a good way to export and import into WP, if it's available.

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When importing (custom) sites I prefer to first have the two sets of tables (the custom one and the wordpress one) in the same database. Then, it's "just" a matter of identifying where the data you need is located in your tables and start creating the inserts that will fill the corresponding fields in the wordpress tables.

You may want to take a look at converters for other systems to get some examples that may give you some inspiration

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You can use wp-api from which you can insert post to wordpress via post method, like json method.. http://wp-api.org/

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