TurnHere.com shows you the world through video and Google Maps - This is a cool site that marries Google Maps with descriptive video to provide tourists (and locals) with an opportunity to learn about cool neighborhoods. The films are unique in that they give an insider's view of parks, restaurants, bars, art galleries, open air markets, bike routes, and more. TurnHere has even teamed up with Google Earth to provide users of the program to be able to link to TurnHere videos. This new feature flags the locations of TurnHere films and allows users to view short films about the area that they are surveying. Here are some example videos (see Google Maps panel): San Jose & Hamakua Coast.
MyOutdoors.net lets you map your outdoor activities - Here's another DIY Google Maps tool entry with journal integration that lets you detail a walk, hike, run or pretty much anything taking place outdoors. The Google Maps waypoint interface is pretty cool allowing 3 separate options to browse the activity you are viewing. Image uploading and full text search of each journal entries is in the works further making this a great site to just explore as well.
Stickymap lets you create "wiki" style maps- Developed by 3 Yale grads, StickyMap is an interactive "wiki" style map website allowing users to annotate map content by creating graphical points of interest. It allows its members to create markers, edit and remove content, and explore new areas. A handy feature allows you to link directly to a view within the site. The site has just started up so it definitely needs users adding content to make it a useful site for exploration, so get going! To check out heavily described areas see New Haven, New York, Boston and Washington DC, USA.