For Toronto, check out boneshaker on instagram, he may have a ride when you are in town. Nice guy and may be able to hook you up with a bike.
My suggestions will be more downtown west side as that is where I live.
For bike shops, not vintage, but if you like road bikes check out blacksmith near Ossington. They have the crazy stuff you only see at teh shows. If on/near Ossington go to Bellwoods for beer. Get a pastrami sandwich at Linnys and drink/eat in the park.
Hendersons is also pretty good for local beer.
I'd also recommend 416 Snackbar/Shortturn at Queen and Bathurst for drinks and samll plate eating.
If you are a fan of The Bear TV show, if on a budget stop at Matty's Patties or Prime Seafood Palace if you want to splurge.
If you want to trek to the east end of the City, or are driving on the 401 - stop at Sumilicious for a sandwich. Compare Montreal vs Toronto smoked meat.
Also in the east end is the feathers, a bar with crazy scotch collection.
If you have any specific questions, drop me a DM.
