Best bet around Park and Tremont w/out reservations and with a crowd?
Gosh, this is such an odd question, and I am not sure if I could have answered it if someone asked it in my home board, but lets try...
I will be heading off to Boston soon for a work related function. I will dine out by myself one night or two based on the information I gathered at this board here (Looks like Via Matta and Union Oyster House for now, but we'll see). For lunches, I have a local friend from Cambridge and he will show me around. So all is set, or it seems; I have a dinner dilemma: We need to go out to eat one night with the colleagues. And here is the catch: we won't know how many people will tag along, and this is a major problem since I cannot make reservations for unknown number of people between 4 and 15.
The conference hotel is around Park and Tremont. So unless it is absolutely necessary no-one will take a cab, to, lets say, Cambridge. We are not talking about chowhounders here. They would be OK with most mid-range restaurants and cuisines, but they won't travel for food. I, on the other hand, don't want to waste a meal in this city and would like to get the best possible food I can get for this dinner.
Let me emphasize the seriousness of the situation by giving examples of where we previously ended up at similar meetings: A Chinese restaurant that also served sushi in Orlando, a faux Italian joint in San Antonio riverwalk, and (cry) McDonalds in Goteborg. The last one was the most painful. I got my revenge by bingeing out on meatballs and really stinky herring the next day; but I think I still have some scars left from this instance. So I guess I'll be OK for anything better than McDonalds, but if I channel all my good energy, what is the best place that I can go with my unspecified number of colleagues, by calling an hour before, or just showing up? No specific cuisine restrictions. Anything is doable, well unless it involves balut or live octopus.
So here is the summary of my constraints: The place needs to be close to Park and Tremont, price needs to be mid range (or less), and most importantly it should easily accommodate drop ins of potentially large parties. So given the parameters, where should I head my peeps to to have the least "wasted" dinner?
While not the most houndish, but I think would fit all or most of your criteria is Ivy. An Italian influenced place that does entrees and small plates and can most likely accommodate your group on a whim. I find this place to be a safe haven with non-hounds. approachable food, kinda hip surroundings and reasonable pricing.
There are better options in the area, but the possible randomness of your group size may rule some out.
Also China Town isn't a far walk and the larger places can handle a large party without any problems.
Union Oyster House-Make sure you sit at the oyster bar and only order off the raw bar menu.
In addition to the others, there's Vinalia on Summer/Arch St. across from Macy's. It's not the most thrilling place in the world, but they have some interesting menu items and could handle a random group.
KO Prime might be kind of slow too depending on what day it is but fairly pricey as is Mooo.
A little expensive for what it is, and not particularly extraordinary food-wise, but close and usually pretty quiet/empty: Scollay Square. Most entrees in the low to mid 20s.
Kingston Station has surprisingly good food considering the youthful crowd that favors it. French brasserie type fare, an excellent prime skirt steak frites, decent with a crowd. Its Faneuil Hall singles-bar scene is kind of scary late on weekend nights, the air thick with the scent of Acqua di Gio and desperation.
You might be able to walk into the dining room at The Good Life if there's no DJ-type event going on. The food is quite respectable and a pretty good value for the neighborhood, kind of comfort New American.
If you're willing to early-bird, walk over to Chacarero for their awesome namesake Chilean sandwiches; they close at 7pm. More of a Chowish lunch option, one of the best in the neighborhood.
If American pub food, excellent beers, and cool old 19th-century tavern atmosphere fit the bill, try Jacob Wirth's. Just avoid the German food on the menu.
If it's more of a wino crowd, consider Les Zygomates. 40+ wines by the glass and good, very traditional French bistro fare. Live jazz on one side, quiet on the other.
Via Matta (the enoteca side) would actually be a decent option for a potentially large group. The full menu is a bit pricey, but the cafe menu has more reasonable options like fancy pizzas.
You might get away with walking into Taranta with a large crowd; just call ahead before you try. One of the better mid-range North Enders, Central/Southern Italian with Peruvian touches on some dishes and a lot of very fine seafood.
Mooo.... and KO Prime are not mid-range: they are luxury steakhouses, most entrees in the mid-30s or higher.
Avoid the Union Oyster House: its food (with the exception of raw oysters *only* at the downstairs oyster bar) is wretched.
re: MC Slim JB
Thank you everyone for the suggestions. I am curious about the Union Oyster Bar comment. I will be there for the raw bar and a couple of pints. I am not thinking about anything fussy, but must have good oysters and maybe some chowda. So do I have a better chance of getting good oysters (and mind you it is getting warmer in the ocean) at another place? It doesn't have to be fancy. I am a female dining alone; but gritty, I can do. Worst case I'll swing some kung fu.
I'd encourage you to go to Neptune Oyster in the North End for oysters instead. It's an easy walk, and they have a lot going on besides oysters.
If you sit at the first-floor raw bar at the Union Oyster House (right near the main entrance), at least you will get your oysters freshly shucked. Tables elsewhere get pre-shucked clams, ick. In general, it's an awful tourist trap.
re: MC Slim JB
Second Scollay Square for relative price and convenience - as MC said, not great food, but not bad. It is the most convenient pick only.
Another place that would be perfect in terms of variability of size is Johnnie's on the Side (in the old Anthem space), which is about a 10-15 minute walk toward the Boston Garden. The room is huge and it is never packed. It's a little out of the way, but pretty much guarantee there will be space.
What about Silvertone? I know it is not really built for the high end of that size group, but they have that extra room, that often is not in use it seems. It's also a stone's throw from Park/Tremont, so it may be worth a fly-by.
In addition to Taranta, you could just stroll the North End for a reasonable place. Check the board for recs in general - it is only a 10-15 walk through the Faneuil Hall / Quincy Market area to get there. A place like Pagliuca's, which I don't feel is ever very busy and serves less expensive, decent, but not flashy Southern Italian might work nicely.
For this situation I'd suggest the Kinsale pub. It's right on Tremont, across from the Gov't Center train station. A 2 minute walk from the Omni Parker. An Irish (faux but who cares) atmosphere, fun for a group and they are very accomodating when more people join the party. Plenty of outdoor seating too which is a nice option. The apps are standard buffalo-wing stuff; the steaks are surprisingly good.