Well, I would keep the following in mind. Cheap food, cheap drinks, variety and being able to hear yourself talk to the person sitting next to you... priceless.
Not sure if the Bruins or Celts are playing that night, but the Sports Depot is a sports bar with a bunch of large monitors to watch the game... Pool table, dart board, but you need to bring your own darts and a CD machine, free popcorn... and it is never crowded and the food is large in variety and not expensive. Plus the beer is cheap and you would not be disappointed.
Not sure if Sylvan St offers all of that. Last I remember they were pretty much just a place to go eat with a lot of noise...Am I getting old?
15-20 minutes from Centennial Dr in Peabody, 40 minutes from Wilmington, 15 min from Seabrook, Not sure of the time to Rockport, but if I remember it is 45min from Gloucester. It is located 20min from Saugus and 40 min from Boston.
Just let me know what is decided.