Redding is pretty spread out. You have the area near Wilton / Ridgfield, which will give you more options in terms of shopping & food. Then you have the area by Easton, which has very little options (the Spinning Wheel is around there someplace, as is the BlueBird diner). It's not a bad town by any means, just that depending on where you are, you may have to travel 25 minutes to get anywere. Where are you moving from?
Redding is one of the last towns in Fairfield County that didn't go commercial. I don't *think* there's even a grocery store in town (could be wrong though)...pretty much the post office, the bank, etc. And the townspeople LOVE it that way!
The only resto off the top of my head is the Redding Roadhouse:
Its a cute little spot out of the way....but most people go here for ambience over food.
You'll have to out source probably most of everything. Depending on which section of town you're in....Wilton/Ridgefield, Danbury/Bethel, Trumbull/Fairfield will more so become your regular haunts. Not sure if you've been to a Stews yet, but there's one in Danbury.
Zobot's recommendations are spot on (LOVE the Schoolhouse).
I always thought however the Georgetown area was associated with Weston rather than Redding (I grew up in Weston so I may be wrong). There is a small grocery store over there as well called Carlucci's (?) - but I couldn't tell you a thing about it becuase I probably haven't stepped foot in there for 15-20 yrs.
But most of all, don't worry....you'll find everything you need close by. And enjoy how lovely and untouched Redding is if you do end up moving there.
You must go to the New Pond Farm, it is the cutest farm that sells, fresh milk, eggs, cheese and the best yogurt I have had to date. It is a gorgeous piece of property. I went to the cleanest best pizza place in Bethel but I forget the name sorry but it is next to a cute Italian restaurant that looks like a European spot. Good luck and it is my favorite town in Fairfield County.
The Georgetown section of Redding has a few restaurants on Main St. Off the top of my head I can think of Delfino's Seafood, the Georgetown Saloon, and Rancho Allegre. I really like Rancho Allegre for Mexican food, I think it's one of the better spots for it in all of FFD county.
That section of town should also see growth over the next several years if the Georgetown Land Development Co is successful at creating a village on the old mill property.
You definitely need to visit the Schoolhouse at Cannondale. It's a fave here among fellow Hounds. It's in Wilton, only a short ride from Redding.
In nearby Ridgefield there are many restaurants. A couple of excellent options are Bernard's and the Elms Inn.