Wikipedia Randomizer
This link will show you a random Wikipedia entry.
Hotline Webring
Join and old fashioned webring.
url.town
A Web directory curated by the folks at Omg.lol.
Bukmark Club
Directory of blogs and personal websites with a bookmarks page that showcases other blogs and websites.
Marginalia Search Engine
Indie search engine that prioritizes non-commercial content.
BlogScroll
An open directory of blogs and personal websites.
ooh.directory
A collection of over 2,000 blogs on many topics.
Kagi Small Web
Random posts from across the small web.
Wiby
A search engine for the “classic web” and small web. Has a great randomizer button for discovery.