I've seen at least half a dozen options out there to measure, track and/or share running routes so I figure a review is in order.
Microsoft Streets and Trips (Client software). I have to start here b/c I use this one more often than any other. Its raison d'etre appears to be providing driving directions and whatnot for Car People. It has a sweet "Measure Distance" feature under the Tools menu (Ctrl+E is the shortcut) that lets you draw a line on the map and get a distance. You can click-and-drag to draw a curvy line or you can just click to mark each point and the software connects your points with a stright line. The line doesn't have to follow streets (in fact it is completely street-agnostic).

Pros: fast, responsive UI for drawing routes; draw-a-box zooming is nifty
Cons: price (not free); no connectivity/sharing
GMap Pedometer (http://www.gmap-pedometer.com/). This GMap mashup appears to be leveraged by a lot of the other run-mapping sites out there - some let you import maps that you drew here. You draw a route by selecting a series of points on the map. Select a point (by double-clicking on the map) and the map will automatically re-center itself on that point. The site automatically adds mileage markers as you draw your route. But sometimes the end-of-route or mileage markers get in the way of adding a point. Single-click and drag to scroll the map - or just add a point near the ege of the map and let it auto-scroll. You can also pan & zoom using the standard GMap controls in the map's upper left corner. When you are done with your route, you can click a [save] button which gives you a route ID & a hyperlink to find the route again.
It looks like nearly 1 million routes have been saved by gmap-pedometer users. This is up 100% since I checked them out last October. This means that they're getting over 75,000 saved routes per month. I reckon a large number of users have also clicked around & measured their route without clicking [save] to get a route ID.

Pros: free!, web app - accessible anywhere; maps can be imported into other sites
Cons: no sharing/community features; only way to remember your routes is to bookmark or write down the ID
Favorite Run (http://www.favoriterun.com).
Usage is about 1/10th of gmap pedometer, with just over 90,000 routes uploaded. This number is also up roughly 100% since I checked last October, meaning the site gets about 7500 routes uploaded every month. This site stands apart from the first two tools I looked at in that it has Community features - forums, blogs, articles and user accounts. The niftiest feature here is the ability to search for a running route in your area. I found 14 uploaded routes within 5 miles of Microsoft's zip code (98052).
The route-drawing interface is identical to gmap-pedometer and you can import routes that you drew there if you know their Route ID number.
In addition to advertising (which is significantly more invasive/annoying than on Gmap-pedometer) FavoriteRun has a paid subscripton model. For $11.95/yr you get elevation data on your routes, some kind of Garmin GPS integration and a few more statistics on your running log.

Pros: search for a route; search for a running partner;
Cons: pages are a bit slower to load and the ads can be distracting/annoying
http://local.live.com - Microsoft's mapping site added a route-drawing feature to their Collections about six months ago. Once you discover the constellation-like button on the bottom of the scratch pad, the route-drawing UI is clean and lightweight. Once ou are done drawing a route it automatically gets added to whatever collection you have open - generally an unnamed, unsaved collection that is empty unless you have used this feature before.

Pros: free; drawing UI simpler than GMaps; sharing feature exists
Cons: sharing is a little bit clumsy right now; feature isn't highly discoverable or advertised;
http://www.run.com - A new site that only has a few hundred routes so far. They use gmaps but have a slightly different look and feel from the other sites mentioned above. They cap routes at 75 points - this can be a bit limiting but I have seen gmaps slow down a lot when routes get long so this limitation probably improves usability... that said, the type of user who is eager to go draw their route on a website is probably meticulous enough that they want to enter hundreds of points...
The route editor is the best run-specific editor that I have seen. You can add point of interest along the route. There are a few specialized text-entry fields - route description, direcitons to get there, tags, neighborhood... the only drawback I see - I feel more comfortable with teh MS Streets and Trips approach to map scrolling than the GMaps approach - I don't like having to center the map before I zoom.

Pros: search for nearby routes; much faster page loads than FavoriteRun.com; UI design; nifty symbols on routes; elevation data
Cons: 75-point limitation; new site - not a lot of routes yet; gmap UI
http://www.runtheplanet.com - appears to be built by the same guys as Run.com. Claims to be "the largest worldwide running community on the internet." Seems like a dubious claim - I see 90 uploaded routes in the state of Washington whereas FavoriteRun has thousands. This site's UI design & look-and-feel are the nicest looking of any of the sites. RunThePlanet also has a nice selection of articles that seem well-integrated into the site.
But this blog entry is about the mapping feature and RunThePlanet is getting out of this space. Some (but not all) of the site's links to Find a Route take you to Run.com. The route-uploading feature that RTP once had appears to let you specify a city and write a paragraph describing the route. You don't actually draw the route on a map.

Pros: informative content; nice UI design; pages load really fast
Cons: routes described in text only
Nifty Improvements that nobody is doing yet
* Route drawing with a "snap to street" option. This would be more useful in road cycling than running (as it sbetter for your joins to run on trails). It can be bothersome to try to follow a road with your mouse. You should be able to easily say "follow this road until I say to get off."