The first series of Bandai's Thomas Town was released in 1999 and included five of the first six numbered main characters from the Thomas the Tank Engine books and shows. It established the Thomas Town character design and track system.
The first Thomas Town set in the series is, predictably, Thomas himself. Thomas includes a straight rail with a tunnel portal and a spinning chicken weathervane and a curve rail with an articulated crane - quite nice. This first series of Thomas Town sets had stickers with the number of their set as well as Thomas Town and licensing information on the bottom - I think this was primarily for the licensing information, with later sets having it tooled into the bottom of the rail.
These original 1999-made trains all have darker grey face paint. The licensing stickers on the rear are a very handy way to date Thomas Town and Pocket Fantasy characters.
Edward with two sloped curves and an elevated bridge section with a signal that can spin to show different colors.
I don't have an original 1999 Edward - the one shown here is from 2001 and has a brighter grey face.
The Friendly Percy set includes a straight section with a pedestrian crossing and the fence and bench of Ffarquhar station as well as a turnout rail and two trees.
The 1999 Thomas Town 1 Percy. I've come across two of these.
Henry includes a straight track with a tunnel, a lifting drawbridge, and a curve. The track in this set has two simple rails as opposed to the more detailed track pattern with sleepers seen in the later series.
1999 Thomas Town Henry with dark grey face.
Friendly James with a two-bay shed and turntable.
1999 Thomas Town series 1 James.
I forgot to put the two little trees out when I put all the sections together...