I'm a Stamford native now living in Norwalk. Born in 1950. We ended up going out that night in Stamford's South End. There are two nice restaurants in a corporate park that have outdoor bars overlooking a marina, which is where we smoked. They are the Paradise Cafe & The Crab Shell. I'm sure they have web sites.
The setup @ the Paradise is more conducive to cigar smoking. Personally, I would be uncomfortable smoking cigars @ the Crab Shell because it usually very crowded with a live band frequently performing. There is much "eye candy" at both places. Check them out if you're ever in the area.