I'm looking for a place that is T accessible in either Boston proper or Cambridge that is known for unique or at least outstanding cocktails and also has great food. I'll be visiting my boyfriend for restaurant week in March so prefer some place taking part in that, but not required. He is much more the foodie than I am, so a place that is more "traditional/American" would probably be best, but I'm open to other possibilities. We are more vodka/gin drinkers, although he is also into whiskey, than rum or tequila if that helps narrow options down. The place does not need to be uber-fancy, but a place that is more than just bar food. Hope this isn't too vague of a description :)
I think Eastern Standard fits the bill about perfectly t if you are having dinner as well. One of the top 2 or 3 cocktail spots in Boston, along with above average Continental/new American food (well, Deep Ellum also has above average food, but as you say you are not looking for pub grub).
No. 9 Park would also be a fantastic choice but it fits into the uber fancy/uber expensive category (up there with L'Espalier and Clio).
774 Boylston St, Boston, MA 02199
528 Commonwealth Avenue, Boston, MA 02215
Deep Ellum Bar
477 Cambridge St, Allston, MA 02134
re: Canadian Tuxedo
It doesn't sound like the OP is looking for haute cuisine, therefore Craigie really isn't a fit. One would be hard pressed to call their food traditional. Also they don't do RW and the prices are quite expensive.
I would second Leo's recommendation of Green Street for food and drink, though they don't participate in RW. They won't sneer if you order a vodka and soda as the staff at Craigie might, but still have the chops to make excellent specialty and classic cocktails.
With the caveat that food recommendations get a lot less reliable during Restaurant Week:
The Citizen Public House and Island Creek Oyster Bar are two newish places that come to mind with terrific cocktails and good food at not top-tier prices. Hungry Mother, Rendezvous in Central Square, the bar at Chez Henri, Highland Kitchen, Gargoyles, Toro and Franklin Cafe (South End) are some others. Dinner at Sportello and cocktails downstairs at Drink might also serve.
1704 Washington St, Boston, MA 02118
1 Shepard Street, Cambridge, MA 02138
150 Highland Ave, Somerville, MA 02143
Cambridge, MA, Cambridge, MA