Definitely better in summer, though I'm not a big outdoorsy person so I couldn't suggest too much in winter...
Eat cheap and in better restos - whether it's poutine & dogs, smoked meat or fine Steak & wine, Montreal is just kick-ass in the gastronomical area.
Check out Old Montreal - cathedral, architecture, museums and galleries, bars and more restos, cool little streets...
Science Museum, or in winter there's festivals and happenings all over the place too.
Catch a ride to the top of the Olympic Stadium.
St-Laurent street - more bars, more restos, shops and boutiques, a shopping addict's mainline.
St-Joseph's Oratory.
Foufounes Eletriques - catch a show or just have a pitcher; pretty cool punk/alt bar.
Mount Royal Park (or Parc Mont Royal) - pic-nic areas, foresty walking paths, city views, Beaver Lake for the water-paddlers (no swimming); ski trails and sledding hills in winter, ice-skating on Beaver Lake...
La Ronde amusement park - fun as much for the weird old-school type rides and attractions as the new stuff - don't think it would blow away the major US parks though.
We have more of all that stuff (more bars, more restos, more shops, more boutiques, etc., no roller coasters yet) in our underground city too - just hop on a Metro and ride to McGill station as a starting point and go all over the place from there.
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