If you're a vegetarian/vegan who loves to dine go to Hamersley's
I went to Hamersley's Bistro the other night to check out the new spring menu and I was really impressed with all of the vegetarian options. Their menu always has the vegetarian section and now vegetarian/ vegan. I'm not a vegan, but as a vegetarian who loves to dine, I understand how much more difficult it must be for vegans to go out to places and experience exciting, flavorful food. The choices at Hamersley's were unique and creative, in fact, everything looked so great I was having trouble deciding what to get, so the chef did a tasting menu for me so I could try a bunch of different things. The dishes that they made me had tons of different vegetables, yummy cheese, perfectly cooked lentils, subtle sauce and spices combined to compliment each other and contribute awesome flavor and texture. It was a perfect, healthy spring meal. I'm not a dessert person, but I couldn't resist my friend's rhubard crostada with lavender ice cream.
Along similar lines, on my recent visit to Upstairs on the Square in Cambridge, I noticed that the menu now expressly says that they offer both vegetarian and vegan tasting menus.
Although UotS had fallen out of my high rotation for a while, my latest visit was good enough to bump it back towards the top of my list. I'm not a vegetarian, but I've dined there with many friends who are, and they tend to be pleased with the available options.
Loads of vegans live in this area. And I do believe that vegetarians are disproportionately over-represented in kitchens (based on who I've met, over the years) ... so ... it makes sense to call ahead to an upscale place and inquire or let them know you have a vegan in the party.
Many places might accommodate dietary restrictions off-menu - with abit of advanced notice. It can be a real point of pride among culinary professionals to provide a unique meal, within reason.
That was certainly my experience w/ a Boston vegan friend, dining in Montreal. Tons of young vegans up there too, working in the food industry.