[Part 2 since apparently the reply was too long - Reddit was invented in the boston area (and of course now i'm getting "you are doing that too much. try again in 9 minutes." - do you see how paternalism is part of the culture?)]
Banking: we like credit unions. Metro CU and DCU are favourites.
I have used credit unions and just. don't. get. it. Feel free to try, since it doesn't cost much, but if you want the bank with the most ATMs locally, it's Bank of America. Free if you have a non-poverty wage job with direct deposit.
If you drive, make sure to get MA plates and a resident parking sticker. There is a yearly excise tax (car tax). Pretty cheap. There's also a "Park Boston" app which lets you pay for meters with your phone. Most of Boston uses coin-op meters. Some areas of Cambridge and virtually all of Brookline has meters that'll accept CC. Speaking of which, there is NO OVERNIGHT STREET PARKING anywhere Brookline. You will get towed.
You'll pay 15 cents extra to use the boston meter app, otherwise it works fine. I suggest keeping 50 bucks in quarters in the console of your car and picking and choosing when to use the app (much of somerville and cambridge do not support app payment).
Don't call the city Beantown. Don't say "FiDi" for Financial District. I'm not sure how people feel about "The Hub", but I never say it.
Just say whatever the fuck you want. People will probably laugh at you (or, more likely, cock their heads in confusion) if you use these names, but nobody cares.
Don't pluralise Boston Common. Just say "The Common" (rather than Commons).
This is correct, but pedantic. Some people will smirk if you say "commons" but nobody will key your car.
Don't say "pahk the cah in Hahvahd Yahd". There's no parking there. But sometimes, you'll see a security vehicle.
This shows up in every newcomer to boston guide and I've never heard anyone say it seriously. I will laugh if you say it jokingly.
A "Coffee Regular" at Dunkin Donuts will get you cream and sugar in this part of Massachusetts. Whereas, in Berkshires, people will give you a black coffee - like in NY.
Jesus christ, this is the best piece of advice in the list. Dunks doesn't get coffee. If you ask for "light cream" they'll assume you want a coffee that's light in color and give you 6oz of brewed coffee in 24oz of half and half. If you like dunks, more power to you, but the coffee's different than most national chains. Plenty of starbucks if that's your thing.
We love Market Basket here, especially since the infamous employee strike. The store is basically a regular grocery - but is cheap. Personally, I shop at Wegman's.
Yes, if you have Wegman's access, it's better. Market basket is great, cheap, and very crowded (but better in the outer suburbs and New Hampshire). There are no terrible grocery store chains in New England - Shaws/Star Market and Stop and Shop are both good. Whole Foods is as you're used to everywhere.
Places to visit: Public Garden, The Common, Arnold Arboretum, Harvard Yard, Boston Public Library (check out the courtyard and reading room), Castle Island (and Fort Independence), the Fens, Revere Beach, Museum of Fine Arts (free Wednesday's after 5), Institute for Contemporary Art (free Thursday's after 5), Aquarium, etc, etc.
Harbor islands are great too, and not too crowded. Ferries leave from Long Wharf (and Hingham some seasons, but I don't think so the last couple years).
Legoland Discovery Center and Boston Children's Museum have a monthly "adult only" night.
Yes, haven't been.
GET A LIBRARY CARD. Libraries have a limited amount of FREE TICKETS to the Aquarium, Fine Arts Museum, Museum of Science, etc for MA Residents. Most people outside of Boston don't know this. Reserve yours 1-2 weeks in advance and go!
Yes, great idea, boston library (and local libraries like cambridge) have ebooks available too. Bank of america cardholders (debit is fine) have free museum admission many places the first monday (?) of the month.
MA has no happy hour, but some places run All Day Specials.
Food happy hour is allowed, which often makes up for it if you're not looking to drink a lot.
Check out Harpoon Brewery, Sam Adams, Trillium, and Mystic Brewing Company (in that order).
Good recs.
Drink at Sunset Grill. Regular sports bar, but has 110+ beers on tap. Also Publick House, Lord Hobo, and Tip Tap Room for something nicer.
Good recs. Four horses (Davis Sq, South End) and Bukowski (Cambridge, Back bay) are other good beer bars.
Cocktails? Drink, Saloon.
Not into cocktails but have heard good things.
Read up on TheBostonCalendar website for events that don't suck.
Same as above.
Check out websites for Great Scott, Sinclair, Brighton Music Hall, MiddleEast, House of Blues, Midway Cafe, Orpheum Theater and a few others to see whose coming to town.
Same as above.
Check out Wally's Cafe. World's best live jazz, every single night, no cover fee, a landmark. It's small though and packs up.
Note that this is in a nexus of so-so and bad neighborhoods (google "Methadone Mile"). Just keep your wits about you and don't get too drunk if you go.
Good luck, have fun, welcome to town.
___ EDIT: While Gourmet Dumpling House in Chinatown is awesome, Taiwan Cafe just around the corner is every bit as good (or better) without a 45minute wait.
If you're going to North End for dinner, bring cash. Many places are cash-only.
Charlie's Kitchen has the best Lobster Roll special around, $8.99 and comes with fries. It's far from the fanciest - but it's real fucking lobster and it won't break the bank.
Oysters! I won't reveal my favorite spots because they're already pretty crowded - but there's a lot of places with happy-hour oyster specials. Many places have 'em delivered from Duxbury, which is a half hour from here.
In Boston, Western MA is considered anything west of Worcester. In the Berkshires, only Berkshires are Western MA, whereas Pioneer Valley is Central and anything beyond Worcester is Eastern.
Avoid Mattapan. Dorchester is hit or miss.
Piers Park in East Boston has the best, most romantic views of the city. Also, Chelsea Yacht Club. If you bring a date here for a picnic as the sun is setting, you're guaranteed to go knee deep.
Don't go to Prudential Tower Observatory. While cool, it's expensive as fuck. Instead, go to the restaurant one floor beneath (Top of the Hub). Get a drink at the bar, look at the view, and enjoy yourself.
The Esplanade: walk it. Boston side is way cooler for the park. Cambridge side is better for the city views.
This is a great bike ride, and you can go all the way out to Waltham if you wish.
Shop at the newly opened Assembly Row Outlets. Cheap designer clothes. Also, MA has no tax on clothes for each item under $100. Woo!
/r/BostonSocialClub for activities, but not as active.
Like board games? Knight Moves Cafe.
Oh, visit Aeronaut Brewery. They have good beer and events (live music and such).
Haymarket is weekends during the summer. It's the oldest outdoor public market in the country. Go for cheap produce, meat, fish, etc. Don't be a tourist: haggle the price! It's okay! And towards the end of the day, vendors are practically giving away food.
Note that this isn't a farmer's market and you're buying nearly-expired produce much of the time. Think of this as somewhere to buy stuff for dinner tonight or tomorrow.
Need electronics but hate Best Buy? Microcenter.
Great store with a good DIY section. Puzzlingly for such a DIY friendly town, not many good electronics stores, but You-Do-It electronics is the best one not mentioned.
Avoid Guitar Center: try Mr. Music instead. It's a one of a kind place.
Brookline Booksmith is awesome. Go there. They have weekly book signings and famous authors actually go. I mean, Chuck Palahniuk is coming tomorrow FFS.
Speaking of which, Coolidge Corner Theater is an awesome small independent movie theatre. Worth going to if you love film. Most people go to Assembly Row or Loewe's downtown.
If you want to save money, like I do, check out Apple Cinemas at Alewife. Every Tuesday, movies are $4.75 all day (after tax, even). It's a SHITTY theatre, but you can't beat the price. And they play new stuff. And Bollywood.
The mall is a bit dumpy and crowded but there's a whole foods and a good liquor store (oddly, across the street from a bad one) here too. The McDonald's is not up to snuff - old fryer oil so fries taste funky and they're kind of one of those nickle and dime shops about sauces, etc.
The Somerville Theater is cool. In the basement is The Museum of Bad Art. You get admission only with a movie ticket.
You'll spot Keytar Bear from time to time. We all love him.
Summertime has free Shakespeare in the Common. It's really well done, has modern music and sets, but all that classic acting and dialogue. Really cool thing to do if your parents are in town or if you want a cheap date. Bring a blanket to sit on.