The Wines of Colorado
8045 US-24, Cascade, CO 80809
(719) 684-0900
Google Maps
Worth checking out if you are into wine, but the indoor dining room is smaller. So I'm not sure what wait times will be like edit* in the winter. It's super chill and romantic in the summer because it's by a creek. It's also a little outside of town in the mountains though. Pretty drive
Rocky Mountain Brewery
625 Paonia St, Colorado Springs, CO 80915
(719) 528-1651
Google Maps
One of the better brewerys in the area
Cy's Drive-In Restaurant
1833 W Uintah St, Colorado Springs, CO 80904
(719) 630-7008
Google Maps
Diner that claims to have come out with the Big Mac prior to McDonalds.
Beyond that, Manitou Springs, and Old Colorado City are cute little downtown areas to explore.
I'm at a loss for really fine dining, but its been 10 years lol. Those are places I miss though. Maybe someone else will chime in.