MY bro lives in stroud
Not sure about trails, although if you get an OS map of the area and find a bridleway heading out North or N.E ish I'd bet you'd find something out that way. Alternatively could ask at Noahs Ark, bike shop a couple of miles out along the Cirencester road.
Plenty of nice pubs, fairly hippy/guardian reading kinda place (one of UKs first Fairtrade towns, Woodruffs in the high street was UKs first all Organic cafe I think)even has it's own local currency that you can use in some independant places (the Stroud pound)
Plenty of good cafes to eat during the day (Star Annice, Mills, Woodruffs) but not so much in the evening that I can think of, but there's the usual chinese / indian / kebabs.
Great farmers Market every saturday.
Should still be a few old school B&Bs in the town – torist info office is in the subscription rooms (which anyone will be able to direct you to.)
It's pretty cool