I love Sushi Main Street (on Mill Street... ). We go there almost every time we're in HMB lately (It's my birthday request) and it's so cosy when the fog is in. I'm vegetarian and can get safe Nabeyaki which is awesome, it comes in a great clay pot. Other than that Pata Moon usually doesn't let down, the Distillery is good for HMB, Duartes is good if you just let it be what it is and it's a country diner that serves great soup.

Cameron's has absolutely terrible food, I mean, it has great British chain pub food (we're in the UK a lot), but it's a great fun experience and casual. We go for drinking there, not for an anniversary dinner. HMB Brepub is one of our favorites, but it gets packed, and they no longer take reservations (we go there 2nd to Sushi Main Stree to be fair, I love the nachos, haha). Sams will have lines down the highway for parking, I hear it's good but I'm a vegetarian and not willing to do that for some fries, and I doubt that's a great anniversary dinner. IIRC, It's Italia had a good brunch.