For sheer quality and decent variety (usually six different kinds which change frequently) I think the best place for oysters is Jasper's Summer Shack. They are usually of impeccable quality. I often find that McCormick and Schmick's selection, while widely varied, often lags in quality. Others, like East Coast Grill, Legal Seafoods, and Brasserie Jo, have fairly reliable quality but not the variety or caliber of Jasper's.
I can't vouch for the quality, but there is a Skipjack's right there in Brookline, on Route 9. Their online menu (link below) does include a raw bar. I used to go to the Skipjacks in Newton pretty frequently for lunch and have never disappointed, although never had my socks knocked off either. I prefer Skipjacks to Legal's, mostly just because it's less crowded.
I have always been a fan of the Union Oyster House. Yep, not too chowhoundly,but they always have big, juicey oysters, and I love that oyster bar..Would I eat anything else there? Nope, just bar food--oysters, steamers and cherrystones..
But I had an apocalyptic experience with Rubee and her SO yesterday..We went to Metro in Cambridge, which has gotten mixed reviews on these boards..There weren't a lot of fish type options, (altho there WAS roasted salmon) which was okay, because I wasn't too hungry..But they DO have oysters...AND THEIR OYSTERS WERE AMAZING!!!!
I usually load mine up w/ horseradish and cocktail sauce, which I did on my first...But then, it was so good, I ate the second naked...And the rest of them the same way..There were 3 different kinds, and I split my order among them...Each one was uniquely different and flavorful...The malpeques were sweet and juicey, the Bristol? (cape Cod) tasted like the total essence of the sea, and the New Brunswick tasted like the fattest, most flavorful bellies of fried clams, with a lick of the ocean thrown in...I'm an oyster fanatic; always like them, often like cherrystones even better because they have more flavor, but this was an eye-opening experience...
And Boston's "Japantown" is downstairs, if you're there during the day, you can do your own noodle tour!! Or do the noodle tour first, then go for a lichi martini and OYSTERS!
I must chime in with a dissenting vote, here. A little less than a year after my fiancee moved to Boston, she and I sat down and "ranked" all the restaurants we had been to, first to last. Although it is hopeless to get them "right" (whatever the heck that means), the process itself was a blast. Lots of culinary reminiscing. My point is this: BOTH of us ranked Union Street Oyster House 89th out out of 89. That's right. We both ranked it last!!!
We are both oyster lovers and the oysters at Union Street just weren't good. Maybe it as an off day, but there were so many flaws. First, only one variety. We love to compare different varieties and the asbence of selection made that impossible. The waitress seemed startled when we asked which kinds of oysters they had that day, as if we were crazy to imply there might be more than one variety! Second, "dead" tastes. They all fell flat. No burst of the ocean. No briny sweetness. No hint of cucumber. Nothing. Very dull. Third, shells and sediment everywhere. A moutfull of shells and sediment in almost every oyster. I would have done better shucking them myslef, and that's an ugly process!
Finally, we did make the mistake of venturing into other parts of the menu. Because there seems to be a consensus among hounds that such a move is, indeed, a mistake, I won't go into the gory details . . .
On the other hand, I am encouraged by the Metro oyster report. Great news that there's another good source around!