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Thanks Alan and Irving, your responses are both very helpful. In reality, these pages have relatively few external links pointing to them compared to other sections of the site, so I think I will opt to redirect them. The newer sections of the site have a nice clean URL structure and good on-page optimization, so I think it's best to bite the bullet and move the older pages over to a new system.

Hi everyone,

Due to some really poor decisions I made back when I started my site several years ago, I'm lumbered with several hundred pages that have overly-nested URLs. For example:

/theme-parks/uk-theme-parks/alton-towers/attractions/enterprise

I'd prefer these to feature at most three layers of nesting, for example:

/reviews/alton-towers/enterprise

Is there a good approach for achieving this, or is it best just to accept the legacy URLs as an unfixable problem, and make sure that future content follows the new structure? I can easily knock together a script to update the aliases for the existing content, but I'm concerned about having hundreds of 301 redirects (could this be achieved with a single regular express in .htaccess, for example?).

Any guidance appreciated.

Thanks, Nick