If you ask me, Boston bread is usually a complete failure. Most of the breads you'll find are either soft, bland, and white and/or unbelievably sweet. Riding on the T this past winter, I could not help but chuckle when a British couple blamed American obesity on the amount of molasses and sugar we put in our breads. Unfortunately, this makes finding a great sandwich in Boston difficult, but not impossible.
Just last weekend, I had an excellent pork fennel sandwich at Cutty’s in Brookline Village, just outside Boston proper. It consisted of slow-roasted pork (a Saturday special), pickled fennel, and roasted garlic piled onto a soft, but yeasty sesame seed roll. The fennel added an interesting dimension to the pork without overpowering the meat. My cashier informed me that their baker used to work at Clear Flour Bakery in Brookline, which explains why the roll was more than just a hot dog bun. This detail also convinced me to purchase their Taza Chocolate brownie, a choice I do not regret. It was the perfect fudge brownie.
The inside of Cutty’s is a mix between a bakery and a neighborhood deli, similar to the Hell's Kitchen location of Amy’s Bread in New York City. When I walked in a little before noon on Saturday, the 10 or so tables were about half full with locals. By the time I left Cutty’s, 15 minutes later, the sandwich line was out the door. The wait is worth it. Their prices are impressively low and their other specialty sandwiches that I tried, the "Spuckie" and the eggplant Spuckie, are just as good as their pork fennel. Go before the bread runs out!