Where to Schlep Your Family
Every neighborhood in Boston has a couple haunts where college kids lo-o-ove to try to fit in their family of nine with two babies on holiday weekends, and where they will inevitably fail and settle for Tony's Pizza & Sanwiches (purposeful typo) around the corner.
The same goes for Things to Do; one time down the the old red brick road is worthy, and enough.
So here's a list to help you not be that kid who's lived in Boston four years and still walks the Freedom Trail to take his family to Mike's Pastry.
For Tourist Family (Or, Things You Should Probably Do Just One Time And Then No More Times)
There are a whole bunch of massively popular eats and activities in Boston that are good - even great - the first time, and then diminish in returns ever after. These are they. Them? They:
Mike's Pastry/Modern Pastry
I mean, them's some big cannolis boy, but size isn't everything. Ahah. The Big Two are really plenty fine, but try Bova's or Parziale's the next block over for no lines, some real Italian baked goods, and also no lines. Did I mention no lines?
Neptune Oyster, Giacomo's, Daily Catch
All legitimately great restaurants, but like the above, there are other equal and/or better places. If you MUST go to one, make it Neptune. Read on for other, better food.
The Freedom Trail
Boston is rightfully proud of its history as the birthplace of the USA, and the Freedom Trail is a fascinating journey through that history. It has all the famous landmarks and dead heroes you were taught about in first grade, and a whole lot more besides. Every time after, however, is just a long walk made longer by History Dad correcting the hapless, red-coated working actor on the details of Paul Revere's ride. Dad, pls.
The Duck Tour
Of all the tours of Greater Boston, the Duck Tour is probably the most fun and the most still-fun-the-next-time. The guides, aside from being kooky characters who know how to handle a massive amphibious assault vehicle, are genuinely funny and chock-full of both Boston facts and lore. Different guides will tell you different stories about the city, and the 1.5-2 hrs will fly by before you know it. Again though, watch out for History Dad.
The Frog Pond
In the summer it's filled with peeing children and in the winter it's filled with bleeding children. But it looks nice.
Union Oyster House
Go for history, for oysters shucked by expert, scarred hands, and for the quintessential clam chowder. Just try to ignore the old-people smell.
Cheers Bar & Restaurant
You've never even seen an episode of Cheers. You'll have to physically restrain your father from cracking a "What's my name?" joke at your server. The show was filmed in LA. Why are you here?
...is good for elementary school field trippers and families that don't know any better. You should. The performers will gouge you for cash, although some of them are seriously talented and hell, you're the one pulling it out of your pocket. Walk through, take a gander, eat elsewhere.
For Sports Family
C'mon, you're in Boston. You've got the Celtics, the Bruins, and the Sox, three storied franchises in three different sports. I'd also say the Pats but good luck getting those tickets.
If your family is less about money sports and more about sports sports, remember that Boston is also The Land of A Thousand Colleges. Winter is Beanpot season, and I never thought I'd say this (as an LA boy who thought the Mighty Ducks were limited to four movies and a cartoon that was basically Teenage Mutant Hockey Ducks), but hockey games are the sh**. Your parents will have a blast witnessing "that college life they've heard so much about(!)," and while your fellow students will 100% embarrass themselves and you, it's hard not to get swept up in the game.
There are also basketball, baseball, and football (you can watch Harvard lose in a cement-slabbed stadium or Boston College lose in a cool big stadium), but they're all easy to look up online and hard to go wrong with, if the college sports experience is really what you're after.
For Active Family
Let's say you've got a mama who wakes up at 4am for her earlybird spin class, eats a banana before pilates at 7am, comes home to meet a friend for a "quick" two-and-a-half hour hike, and if it's Tuesday or Friday, has a whole round of golf in store for the afternoon. And now she's coming to visit. Metabolism, don't fail me now.
Good news: she'll love Boston. The city is about as active-hyped as a city can be, and whether she's a trail runner or urban explorer, there's plenty to do 'round here.
Bad news: you gon be tired, yo.
One of those routes that makes you, for real, want to run in the morning. Even (or perhaps especially) on a windy, late-fall daybreak, doing a loop around the Charles is a stunningly beautiful experience, ruined only by your profuse panting. But that's what music's for, ain't it? You certainly won't find any solitude out here, but this is about as peaceful of a time as you'll find in the city - walk, run, or bike.
Speaking of bike - meet Hubway, Boston's resident millennial bike share(ish) company. Stop by any one of their 180 silver bike racks around the city, get a pass, and you and your fam will be rolling out in no time. Now, Boston's hell on toast to drive in, but casual cyclists have an easier time navigating the city than other transportation, thanks to bike lanes and all. You may balk at urban biking, but one ride on the Green Line should encourage you to give it a shot. Plus it's a small city, so you won't be going that far... right, Mom?
The November Project
An urban fitness revolution started by two Northeastern alums (HusKIES), November Project is a mind-bogglingly welcoming public workout cult group. Mondays rotate workouts around the city, but on Wednesdays they can always be found running the Concrete Slabs of Hell bleachers at Harvard Stadium, complete with motivating rally and what is usually a pretty sick soundtrack. And this isn't some whippersnapping college kid thing; all ages may (and do) attend. Fit Fam will <3 this.
Simple. Go to Charles River. Rent kayaks. Have ball.
This depends on where you live, because as far as I'm concerned climbing gyms didn't exist until I moved into a city. If you happen to have one in your town, then ho-hum, move on. But for everyone else, rock climbing's back, baby. Buy a day pass for a heap of bouldering, auto-catch climbing, cushioned plummeting fun.
For Food Family
A perfect family restaurant experience has two particular qualities: minimal stress and great food. No matter how carefree or sour your family may be, a long wait or bad table can leave your meal in ruin. You don't have to settle for some janky pizza place around the corner from your apartment just to avoid the wait, though. You see, there's this wonderful, magical thing in the world of food appreciated by customers and restaurants alike, but that's often and easily forgotten. It's called a... "reservation."
For lunch and breakfast, reservations are not frequently a thing in Boston, but for dinner it can be a lifesaver. Or a family-saver, if you will.
Sidebar - My family's restaurant is extra busy on the weekends (duh), a rule that especially follows for Big City restaurants like those in Boston. One of our least favorite situations is having a family of eight people walk in at dinner prime time, expecting a hidden table in a quiet corner to be free for just them right now, and then having to basically turn them away with an hour-long wait, minimum. Okay sure, there's a certain smug satisfaction from being busy enough to do that, but that goes away watching Sad Child shuffle back out the door, barred from promised warmth and family fun times.
Anyway - here's a bunch of restaurants worthy of family time, from dinner reservations to brunch rushes:
How better to start a list of restaurants than with not-a-restaurant?
Boston Public Market is the New England kin to New York's Chelsea Market and LA's Grand Central Market, and while certainly a lot smaller and less flashy than its cousins, BPM packs a lot of delicious in its limited square footage. Taza Chocolate, Union Square Donuts, Noodle Lab, Bon Me, as well as a host of fresh seafood/dairy/produce/meat purveyors fill the interior with competing, complementing aromas. But you're not going to want to miss those apple cider donuts (aka apple fritters, apple yummies, apple happys, for obvious reasons), nu-uh.
Pretty much the top of my North End list, this outwardly unassuming townhouse restaurant is one of a few ultimate treat y'self spots, splurging encouraged. Forecast: 100% chance of impressing the hell out of your family.
Like the above, except with some twistier, edgier cuisine (not so much artsy as more modern), Scampo is the place to take a family that really, really loves food. It's located in the Liberty Hotel, which is a converted old prison. A converted old prison. If that's not cool enough for you, go back to New York.
No, not Gourmet Dumpling House. Again, good, but impossible. Shojo is usually shockingly light at lunch when it's open (Th-Sun), and yet it has easily one of the best lunch menus in the city. From frustratingly delicious ramen to Shadowless duck fat fries to simple garlic greens, there's something amazing for everyone here. Call ahead for big fams. Full review right over heah.
Time to getcha seafood on. Boston cuisine is now much more than Italian and seafood, but it's not like those are going anywhere, either. Row 34 does seafood, especially raw bar, arguably the best out of any restaurant in the city.* It's also in the Seaport District, Boston's obligatory former-industrial-warehouse-gentrifiers-wanted neighborhood. You know, where all the hip youths kick it.
*Listen, I said arguably. Feel more than free to argue. Leave me a comment, I totally read them. Totally.
Far from a secret, but still not hard to get into if you wake up before college kid o'clock, The Friendly Toast is the best brunch. (Period). It's big, it's hearty, it's warm, there's unlimited coffee, and the interior is an eclectic mix of auntie's house and Jersey diner. Should bring a smile to even the grumpiest grandma.
Now this one's tricky. Holiday weekends you can pretty much forget about, and Sundays during football season are hit-or-miss, but Ernesto's can be a super easy and casual spot in the North End to roll into with the fam for some kick-ass pizza. First-timers should get a heap of different slices to share, or if you know what you like, settle for a couple fresh, full pizzas straight out of the oven. This ain't no Dominos.
"Who knew Malaysian food was so stinkin' good?"...is basically what your dad will say when eating at Penang. Obviously the Malaysians, Dad. If you can get your family past their dumb associations between Asian cuisine and their own sad stomach issues, Penang is a superb family restaurant, complete with those spinny tables that make plate sharing so fun. Get 12 Roti Canai for the table - hohhhhhh mama.
Most unfortunately for me, Eataly opened in the Prudential Center a few months after I moved out of Boston. Most fortunately for you, it's yours for the taking. Mario Batali's celebration of everything Italian cuisine is just as good in Boston as it is in the NYC original. Three restaurants, put on in collaboration with Boston chef Barbara Lynch (No. 9 Park, B&G Oysters), a host of dessert and sandwich counters, a pair of espresso cafés, and a full Italian market make Eataly just as fun to wander as it is to eat.
Phew, that was a long one. I know I left out Cambridge again. Look, once Shake Shack opened on Newbury, I barely had a reason to go out there. And then Santouka Ramen moved to Back Bay, and I had no reason to go out there. Write me, Cambridgers & Somervillains, wherever you hang with or without the fam, and next article will be alllll about you. As usual.