In Boston it's a tie between
Abe & Louis' or
Smith and Wollensky's.
Grill 23 is also quite nice.
In Montreal, I love
Queue de Cheval and sometimes go to
Moishe's.
Out of all mentioned,
Queue de Cheval is just
The have glass encased bar that is cigar friendly. When Montreal did not have a smoking ban, they would roll a cart to the table filled with Habanos, Port, and Madeira to the table! Talk about a kid in a candy shop!