Lessons from Boston: Something Bold, Something New

It’s Saturday night in downtown Boston. I’m pacing the sidewalk in front of a gastropub, outside with the smokers. I’m not smoking. Instead I’m canceling a 9 p.m. dinner reservation across town at a restaurant I’ve never been to, and making a 9:30 reservation at another I'd never heard of until ten minutes before, all on the advice of a stranger.

Guide books be damned. The decision is made. Now let’s hope it's the right one.

There are lessons in travel, if you’re open to them. More so than just in the discovery of new places or the facts behind a historic sight, but actual instructions for life. A weekend trip my wife and I took to Boston recently contained one lesson that repeated itself to the point of being unavoidable.

We went to Boston to celebrate my wife’s birthday. It was a round-numbered one, so important. She dreamed of going to Italy for this milestone, but with four kids and all the bills that come with that, Boston was the best we could afford -- and we could barely afford that. Still, she was born in Massachusetts, so it kind of made sense to visit the City on a Hill in celebration of her existence. Plus, I’d never been there, despite the wanderlust of my youth. So, to Boston it was.

When it comes to things like vacations, I’m usually a bit of a planner. Before a trip I’ll grab tour books and surf the web for weeks in advance to find out everything I can: Places to eat, colorful markets, sections of town that just shouldn’t be missed. I find it and put it on a list. Then I map out the days of the trip. We’ll wake early, walk here, eat there, shop here, drink this, have lunch at that place, watch this show, dine here, nightcap there, and then back to the hotel. Every day I’ve got a schedule in my head, even if I don’t always share it.

Before this trip, however, things were different.

For starters, we’d both been so busy with work and kids and whatnot that I didn’t do one-tenth the usual research. Second, it was her birthday and her town -- and no place for my annoying vacation control issues -- so I figured I’d just do whatever she wanted. Other than booking hotels, I didn’t make a single list of sights we had to see, places we had to go, or things we had to do.

Of course, once the vacation started so did my obsession with order.

Redefining “Old’ In the Mountains

Getting older is never easy. Luckily, what counts as old is a relative term.

The first night of our weekend we spent at a sleepy inn in the Berkshires, as planned. We figured it nearly impossible to work all day Friday then drive the five hours to Boston and still get there at a decent hour. So we broke it up with a stop at the Red Lion Inn in Stockbridge, a little village immortalized in a painting by Norman Rockwell. The innkeepers also own Country Curtains, and my wife had always been curious about the inn, so it was an easy choice. 

Red Lion Inn -- Stockbridge, Mass.

When we told my mother-in-law we were planning to stay at the Red Lion, she replied, “That place is old.” And that pretty much sums it up.

The Red Lion began as a general store in 1773, becoming an inn in the decades after – one of just a few continuously operating inns from that era in New England. It is old, literally. I’d describe it as closer to charming than worn on the spectrum, but it’s definitely on that spectrum. The wood plank floors, bent from centuries of settling, creak with each step. Doorways lean one way, stair cases the other. I kept telling my wife, the old inn’s been around for generations and would certainly stand through one more night. It did. It was also clean, and the canopy bed proved surprisingly comfortable – an important matter, because when the parents of four kids get away for a weekend, all they really want is uninterrupted sleep.

We’d gotten to town too late to eat that first night, winding up in the old tavern in the old basement just after the kitchen and everything else in Stockbridge closed for the evening. So our hunger woke us early the next day. As my wife readied herself, I inquired with the Innkeepers about a good place for breakfast.

For those who don’t know, I take food seriously. I not only eat it every day, but I also like to cook it, and love to find places that cook it well. We’re not talking fine dining here, necessarily – though I’m okay with that on occasion. I’m more into cool, interesting places with well-prepared food, whether it's a four star restaurant or a street vendor makes no difference.

Finding food is how I like to explore a place and get to know it. That’s why I’m such a fan of Anthony Bourdain. He does it for a living.

Whenever I go someplace new these days, I ask myself “Where Would Tony Eat?” WWTE? If we can find a place worthy of Tony (which is what us friends call him) then it’s a good day. Again, that’s the kind of thing I usually seek out in the research phase of the trip. This time, we had to just ask the innkeepers, who pointed us to the Elm StreetMarket.

I wasn’t at all worried when we had to pass two other places capable of serving breakfast to get to the market, though my wife grew skeptical.


Elm Street Market

On appearances alone, the Elm Street Market seemed my kind of place for breakfast, if only for the questionable atmosphere. It’s a grocery store, butcher shop, deli and breakfast place all crammed into a tiny, little storefront market. Along one side of the store stands a wall of coolers holding milk and eggs. Across from it, separated by an aisle of groceries, sits a five-seat breakfast counter, propping up locals as they hovered over plates of pancakes, eggs and corned-beef hash. Behind the counter, a hulking short-order cook worked the grill, while a frail, older gentleman doubled as server and cashier. We ordered at the counter and sat at one of a handful of tables squeezed up against the storefront windows.

As we sat there, we began to wonder if it was actually the best place in town for breakfast or just the one in the good graces of the innkeepers.

We were starving, so the food did the job just fine. Yet it also answered our question. We later learned the inn actually owns the market and there are better breakfast places – which we passed on our walk there. That morning we learned a general lesson about advice from unknown innkeepers. But that’s hardly the grand lesson of this trip.

After breakfast, we strolled through the village of Stockbridge, self-described as “America’s most famous main street.” Nothing was open yet. A cute town, but if you’ve seen the painting that made Stockbridge famous than you’ve also seen the whole of this quaint little place. Our stroll took less than ten minutes. We checked out of the Inn and headed for Boston.

Along the way, we took a detour through the village of Lenox, another Berkshire mainstay. It had a bit more going on than the more famous one. And, though we thoroughly enjoyed our night in the mountains, we decided that if we ever stayed in the Berkshires again, we’d skip Stockbridge and go to Lenox.

Still, on this trip, we had a grander destination in mind.

Finding Food and Trusting Fate in Boston

I’m not a big believer in fate. People who’ve been through some crap and seen random badness in their lives generally have one of two reactions: either it was meant to be, or there’s no way it was meant to be. I fall in the second category.

I also don’t believe “things will always work out,” as many are apt to comment when things aren’t working out. Maybe that’s why I try to plan things. To give fate a hand, and to make things work out.

But, there’s no denying that sometimes it seems the universe conspires to make things go a certain way, despite our best efforts to push in another direction.  And that brings us to Boston.

We began in Boston as America began -- at Faneuil Hall in downtown. After strolling the shops, the outdoor produce market and the indoor food hall, which was more like a food court than a true market, we were hungry again and ended up in the waiting area of the Union Oyster House, which has the distinction of America’s oldest restaurant. There’s that theme again.

Standing there, convincing ourselves to wait forty minutes for our turn to eat, my wife expressed her concern that we were in a possible tourist trap. I looked around, and low and behold she was right. We also remembered that we don’t like oysters that much. So we left.

Once on the street we wandered in the direction of a few restaurants that were showing up on the Urban Spoon app. That random choice led us to the heart of Little Italy. We’d been told by pre-trip advisors to go there, and I had planned in my head to do that for dinner. Now we were there for lunch.

Boston’s Little Italy, also called the North End, bursts with restaurants, bakeries and bars, and bustles with trendy locals and tourists alike. We were overwhelmed with choices. I was extra overwhelmed because I never expected to find so much of Italy in a town I always thought of as Irish.

We first looked for a place a friend from home told us about, but couldn’t find it. We wandered some more, got hungrier. We settled on a seemingly trendy place, where Tony would likely have eaten, joining a line of urban hipsters that stretched down the block. We stood there, not moving, for too long. Then we jumped out of line and wandered to a fine little Italian place called Gennero’s, with fresh pasta and room enough to feed two hungry travelers right then and there. It was delicious.  



Café Victoria-- Little Italy, Boston

After our late lunch, we joined the masses for an Italian style coffee and cake at Cafe Victoria. It wasn’t Italy, but it was as close as we could get. Full and groggy from the meal and cake, we checked into our hotel to get settled and rest up before dinner.

Our choice of accommodations in downtown Boston was one thing we had little say in. By the time I booked the place, every other hotel nearby was full or way out of our price range. The Mandarin Oriental, for example, wanted over $1000 bucks for their last available rooms -- I'm guessing a suite. So we stayed at the Omni Parker House, which turns out to be the oldest continuously operating hotel in America. Go figure.

I swear I didn’t pick all these old places to make my wife feel young (or old); it just happened.

As it turns out, the Omni Parker House has quite a history, particularly with Boston’s literary elite. As for me – an upstate New York literary underling – I was struck most by how damn small the room was for the price. And they didn’t even have free WiFi. Other than that, there was little to complain about. We could see the Charles River from the window and the bed was comfortable (though a bit small).

One thing I knew about our plan for the rest of the evening, I wanted to have a plan. We spent part of our time at the hotel that afternoon researching restaurants for dinner. After all, this was to be the climactic meal of the trip -- Saturday night dinner, right? I figured, since we’d had Italian for lunch, we should have seafood for dinner. With that, I searched a bit and picked Boston Sail Loft, and then made a reservation. My wife was skeptical of the choice because one review put it on the list of Boston’s “douchiest” restaurants, saying it “is well-stocked with the finest assholes of New England’s famous prep schools.” As assholes go, prep school ones are a special breed. Despite concerns, I needed to have a plan and worried we wouldn’t eat if we didn’t have a reservation. So I booked it.

My wife also picked a gastropub called Stoddard’s near our hotel for a cocktail before dinner. Our plan set, we got ready, primped and headed out for the evening.

We arrived at the gastropub to find a relatively young crowd gathered in the cavernous, rectangular dark wood room, complete with old-fashioned street lamps as light posts and a thirty-foot bar adorned with a long line of taps. When two seats opened at the bar, we sat. What can you say, we're old.



Stoddard's -- Boston

It was at Stoddard's that the stars aligned in our favor and fate, or more likely luck, took over. When this luck arrived, it didn’t come in the package you’d expect, unless a lonely, older woman sitting alone at a bar, surrounded by 30-something hipsters was expected.

I didn’t see her at first, but then she started talking. In the first words I heard, she cursed, “Kids these days and all their politically correct crap.” My initial thought was, are you speaking to me?  She was the oldest person in the bar by decades not years. And she was dressed for going out on a Saturday, her hair in a neat bun. Despite looking worn and tired, she had fight in her voice.

“When I was young comedians would tell offensive jokes, and nobody cared,” she said to me as a more formal introduction. I assumed then I was in for a tough night at Stoddard’s.

Over the next hour or so, this life-long Bostonian shared tidbits with us about her life as a nurse, and how she’d seen it all, and several more things that began with “Kids these days...” I wondered if  she thought we were kids too, or her compatriots.

Eventually, talk turned to our kids, and our lives, and then our plans for dinner.  "The Sail Loft?" she said as she shrugged her shoulders, added a “Meh.”

So, I asked where we should go, and she said told us, “Mare.”  She’d never been there, but she’d always wanted to. It was a date place and for special occasions. She hadn’t had either lately.

At the next lull in her soliloquy on life, I ducked outside and called for a late reservation at a restaurant recommended by a perfect stranger who’d never been there -- and I cancelled our other reservation at the so-called douchy place. An hour later, after our new friend left with half her meal in a bag for her dog at home, we hopped a cab and found our way to Mare – an Italian-style seafood restaurant on Boston’s North End.

To keep this long story short enough that I don't have to get it bound and numbered, lets just say that our meal at Mare was one of the best and most memorable we’ve ever had, second only in my opinion to a Friday night BBQ at Foxy's on Jost Van Dyke during our honeymoon.

Despite changing my sacred plans, we ate well that night in Boston.

I was beginning to see a pattern in our trip, that we had our best luck when our plans didn’t work out, our whims took over, and life and luck led us in another direction. The next day the pattern repeated.

We woke early again, long before 10 a.m. Sunday brunch service. To pass the time, we took a walk through Boston Common – a smaller version of Central Park – headed in the direction of a brunch place on the list supplied by the hotel. After a leisurely stroll, we arrive at the restaurant 5 minutes before it opened. There was only one problem; Nobody else was waiting to go in. After some consternation on my part, and some coaxing by my now wiser wife, we left to find someplace else, anyplace else.

Forty minutes later, we found a much better breakfast option on Newbury Street, Boston's version of Rodeo Drive. Our next few hours were spent perusing the shops -- exactly the way my wife should spend her birthday. The  trip felt complete. And when the early afternoon arrived, I was ready to go home. But my wife had other plans.

She thought we should have one last meal before we left. It was 2 p.m. I wanted to get on the road, sticking to the plan I'd hatched in my head. If we left at 2 p.m., we’d get home at about 7 p.m., I said. But we needed to eat, she said. We needed to go, I said. We hadn’t had chowder, she said. Fine, I said.

Our final quest, in search of chowder, took us to Boston’s Seaport District. Again, I had no idea about the place. But just a short jaunt from downtown we were surrounded by concrete docks and warehouses on one side and new hotels on the other. Interspersed between the docks and warehouses were recognizable restaurants like Legal Sea Foods and Rosa Mexicana. It was industrial longshoreman meets modern development.

I figured we could find chowder at any number of places, if we could only find a parking spot. As a newly burgeoning section of Boston, there seemed a severe shortage of places to leave the car. We drove around for too long, circling the blocks like I used to when we’d go to Adams Morgan for dinner. It sucked. I was ready to go home.

Then we took a wrong turn and ended up next to another old warehouse. We looked up and saw a sign that said, “Parking for Yankee Lobster Customer’s Only.” That was the name of the tiny store front with the red awning we’d just passed while attempting a three-point turn.

“Look up Yankee Lobster,” I said to my wife, who had been Googling chowder places on her iPhone. 

“On it,” she said. Seconds later, Google and other sites reported that the Yankee Lobster was a perfectly fine place for a cup of Chowder. So we parked, and went in.

Thank god we didn’t find a spot earlier and wind up at Legal Seafoods, or some other Godforsaken chain.



Yankee Lobster Co. -- Boston

Once inside the little storefront, we knew we’d arrived at fresh seafood Nirvana. A crowded room greeted us with sideways glances, as people refused to take their faces away from their soup. Fresh fish and lobster crammed the cooler, colorful specials were drawn on the chalk board. Hipsters? There were hipsters. Not just eating there, but working there too.  Hipsters were running the joint.

We waited in a short line and ordered our food at the counter, as was the design of the place. I got the chowder and fresh fish fry. My wife got grilled lobster tail – lobster on her birthday. 

I always ask, Where Would Tony Eat? He’d eat at Yankee Lobster.

We sat outside in the courtyard next to the dining room, because it was too full inside and the sun was shining on us on a warm November day. Then the food arrived.

YankeeLobster Co. is not only cramped, dingy, fresh and beautiful, the food is damn good too.



Thanks, Boston. 
It was fun.

I don’t believe in fate. But sometimes the universe does conspire in your favor. And boy did it. So, on this trip to Boston, I learned a something about plans. I learned that we can make all the plans we want. Plans are good, after all; They give us structure, and help us achieve goals. But sometimes the real beauty happens when we go off the plan and improvise.

It makes me think about the life my wife and I have built. It pains me that I couldn’t take her to the actual Italy for her birthday. And that so many of our plans haven’t worked out like we wanted or hoped.

But I look around at our home and our lives and all the little people in it, and I know that many wonderful things have happened that we never imagined, despite all our plans.

So. That’s it.

I'm going to keep planning things, because that’s what I do. But I'll always be ready to improvise. Because, sometimes luck and fate do take over. And sometimes, things do work out.

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