As noted before in the entry for Bonifacio and Dore, and shown on the “June 16, 2003” World Map (see, for example, here), one of the first five community projects was a fantasy/medievalist roleplay area called “Dark Wood”. When the Color Sims were added, just a few days before the official opening of Second Life, two other regions were created as well. It’s my assumption that was done for the sake of parity with the brand new, second wave of community projects, each of which were receiving their own full sim. Since their establishment a couple of months prior, two of the original five had become relatively popular, earning the privilege to expand. Hence, Darkwood became one of those “extra” two.
If any roleplay occurs there now (which I doubt), it’s at a time of day I’ve missed. Nevertheless, the sim’s builds are almost all themed in a style meant to invoke references to Tolkienesque fantasy. Most of the oldest ones tend to be on the eastern half… but here’s an exception, a little bit west of the sim’s center point:
It was built by Tweke Underhill, whose Hat Tree still stands in Welsh (and whose hardshell crab still occupies the beach under the Beanstalk), in October 2003.
The northeast corner of the sim (lower right in the overview) seems to have all been occupied and built upon during the same month: October, 2004. Among that collection are the Cathedral, and the towers on the adjacent ridge, all by Bill Stirling:
In terms of antiquity, however, the real gems are to be found in Darkwood’s southeast corner:
“Sauron’s Tower” (September, 2003) and a watermill (July, 2003); both built by another member of the Underhill clan, Upshaw.
Saving oldest for last: in the extreme southwest corner is Smuggler’s Den — built by Merriman Brightwillow in May 2003 — which is old enough to have originally stood on the Darkwood community’s old land in Dore, and moved to its final location when Merriman claimed the land in January 2004.
As always, more can be found in the online collection.