Here are some pics of Wagons (and a chariot) that were painted for my Dungeons and Dragons campaigns that ran from '99-'08. Some of the models were purchased specifically for the campaign, and others were already owned.
You will notice an old (20-25 years old) GW Skeleton in most of the pics. I'm not really sure why I put him in these shots as these models don't really need it. But I took these pics on the same day as a series of elemental and giant pics, where the skeleton really did help illustrate scale.
This is a GW Vampire Counts Black Coach that I bought specifically for using as a standard coach. The players started using stagecoaches as their primary mode of long distance travel. We ended up having many encounters in town and on the road centered around coach travel. So I picked up this model. The "conversion" was walling off the back of the coach, swapping skelly driver and horses for health counterparts, adding interior detail by carving passenger seats out of foam, and adding baggage to the roof.
This model was one of my first attempts at modeling a "road", or worn spot in the grassy earth. In hind sight its not very successful. My basing technique at the time was a step up from the previous process, but only a little. Prior to this, I only used one color on the sand covered base (either green or brown). While I am using green and brown, picking out some rocks, and dropping in a bit of flock, it just isn't natural looking.
WAGONS & CARTS
Here we have 3 carts, all from GW. The one on the left was bought for the campaign. No mods on that one!
The middle cart was bought in the late '80. I had a Halfling Merchant in a WHFRP campaign and I needed a pony, so I picked up this mini. The cart had been build on a separate base with a bent wire around the shafts so that the wagon could attach to the horse. It was great that the pony and cart were separate, but I found it cumbersome to use on the table. Wen I repainted them for this campaign, I also put them on the same base.
The third cart was one I picked up on a special mail order deal, back when the catalog was mailed to you and was a black and white folding poster!! I do not recall if this cart came with horses or if they were repurposed. I used horses I got from an inexpensive farm animal play set.
This is an old Grenadier Orc Chariot set I bought in the early '80s. I had used this figure in my early WHFB games. It has gone through 3-4 paint jobs over the years and in all the variations, I always kept the wolves separate. In this latest incarnation, I used a movement tray to allow the wolves and chariot to me moved as one piece. you can see the difference in the basing techniques on the wolves compared to the chariot.
The driver came with the original box set, as did the orc in the rear (I think). I do not recall the company or era of the middle orc.
Here is a shot showing the wolves removed. The banner poles lost both the tips over the years. I replaced them with bits from a GW plastic Skeleton sprue.