- Cannoli at Modern Pastry Shop (North End or Medford Square)
If you grew up in an Italian-American neighborhood, you're already familiar with cannoli: crisp, hollow pastry shells filled with sweetened ricotta cheese and dusted with powdered sugar. If you're in Boston's North End, skip the more touristy Mike's, which leaves pre-filled cannoli to get soggy on the shelf, and head to Modern just down the street. If you're heading north of the city, the Medford Square location has the same great pastry without the lines (except right before Italian/Catholic holidays).
- Molten Chocolate at Finale (Park Plaza or Harvard Square)
Molten chocolate cake has become a classic in recent years. Who can resist the warm, gooey center? The pastry chefs at Finale take this popular favorite to an art form, applying perfect technique to high end ingredients. The result is well worth the premium price.
- Crème Brulée Cheesecake at Not Your Average Joe's (multiple locations)
Sure, Joe's is a chain, but it's a consistently good one that knows how to put out a quality dessert. The cheesecake is rich and creamy, and its slightly crispy caramelized top adds just the right contrast in textures. Go for dessert, stay for dinner, and perhaps try a raspberry-lime rickey while you're there!
- Ricotta Pie at Arthur's Pastry Shop (Medford)
Take a cheesecake and interbreed it with a cannoli, and you'll end up with ricotta pie. The best can be found at Arthur's Pastry Shop in Medford, just a couple miles down the road from Modern Pastry (see #1 above). As long as you're stocking up on Italian favorites in Medford, you might consider a trip to Bob's Foods, an Italian specialty store that also has great subs and pasta dishes for takeout; LaCascia's for more great subs and baked goods; and Italo Bakery for cheap but delicious fresh-baked bread.
- Black-and-Whites at Lyndell's (Ball Square, Somerville)
Also not far from Medford (but more accessible by public transportation) is Ball Square's landmark bakery, Lyndell's. Everything I've had there is great, but I especially recommend the black-and-whites, which are basically flattened cupcakes with half chocolate, half vanilla frosting. They also have every other combination of chocolate or yellow cake with chocolate or vanilla frosting. My favorite is the yellow with vanilla, but the black-and-white is the classic.
Update 2/22/12: Correction to Italo Bakery.