When I was working there, we stayed at the Trail-something motel. Traildust, Trailside, something like that. Not too bad, and definitely has character. Trinidad Brewing Company is a short walk across the main drag and down the hill, and their food and beer was pretty good. The only other really good eatery was Pike something, should be easy to look up. Excellent food and a solid beer selection. I was working in a small town west of Trinidad and it's been three years or more so things may have changed, but do a little searching on that and hopefully you can turn up more info.
Btw I'd avoid Tequila's, pretty average Mexican food. I've eaten at the one in Trinidad and the one in Glenwood Springs and was disappointed both times.