Not really. The 'oldest gay bar in the US' (so they say) which was in Westport closed for good this past weekend. The closest bar now would be Triangles in Danbury, which requires a car (35 minutes north), and is not worth the drive. New Haven (30 miles to the East) has a few, but for Stamford, your best bet is to go to NYC (45 minutes by train). Or alternatively, stay in NYC and take the train up to work each day (very easy to do).

There are a few 'roaming' gay nights at various bars in Stamford, but nothing reliable, in my opinion.