I’m sitting in a hotel restaurant in Pittsfield, Mass., enjoying the hoppy, piney fragrance of a tall imperial IPA when I sneak a glance over at my brother-in-law, Ryan. He’s moments into his first taste of 413 Farmhouse Ale (Big Elm Brewing, Sheffield, Mass.), and it’s not going well.

There’s a long, searching pause before Ryan ultimately says, “Oh yeah ... no.”

Christina’s sister Angela, Ryan and their 7-year-old daughter, Grace, are in the middle of a long vacation out of Springfield, Mo., most of which was and will be spent bouncing around various locations throughout upstate New York. But we took a two-day detour through the Berkshires. One of my goals, throughout this week and a half in our home and in hotels and bars and restaurants, is to throw as many beers, familiar to me and otherwise, as I can at Ryan and to see what sticks.

Ryan’s a Bud Light man, which is to say that in the 10 plus years in which I’ve known Ryan, I’ve known him to be a Bud Light man, a Keystone Light man, a “pitcher of what’s up for a few dollars” man and, once around a fire pit near Hocking Hills State Park in Ohio, a Really Into Yeungling Light Lager man. It’s not that he’s particular or particularly unparticular. There are just too many choices sometimes, he says. There’s simplicity in a familiar order.

Simplicity is not what he got with the 16-ouncer of 413. After a long pause and a few shakes of his head, he says, “It kind of tingles.”

The Farmhouse Ale, a stealthy 6%, is indeed kind of a spicy brew. A Belgian ale brewed with chamomile, orange zest and Saison yeast, has a rich, amber color and comes in with a spicy nose and an almost effervescence in the front from all of that spice. It’s smoother in the malty finish, but the front is all Ryan seems to notice.

“Yeah,” he says after a second sip. “I don’t think I like that.”

I, on the other hand, am enjoying my Big Elm brew of the day, Fat Boy, an 8% imperial IPA that comes on pretty hard after a four-hour drive. We’re watching the Cubs and Ryan’s Cardinals on TV while we wait for our food. Angela, also more of a macro-enthusiast, is quite taken with the 413.

“It’s not gross,” she says. “It’s light, not too … whatever flavor there is in beer.”

“Hops? Malt?”

“Yes.”

Success ... I guess. But I still consider this a failure.

Now this wasn’t a trip about beer. Not exactly.

Christina hadn’t seen her sister in over two years. Both distance and the plague of 2020-21 made getting together difficult. Even with all four of the adults vaccinated, Grace, 7, and my boys John, catching up to her in October, and Ben, 4, were and as of this moment still are not eligible to receive the COVID vaccine. So neither they nor us have traveled much over the past year and a half and we certainly haven’t seen one another. The kids, all close in age, have grown up with one another over the phone. Games of Roblox and endless jokes where the only punchline seems to be “poop.”

They’re getting old enough to start really remembering things, and it made both Christina and I and Ryan and Angela sad that the kids couldn’t really remember a whole lot about one another that didn’t involve freaking FaceTime.

So after a few months of planning, Ryan and Angela split shifts on a two-day drive from Missouri, no doubt made possible by Grace needing far fewer stops than either of my two boys would have. The plan was for them to drive out, and we would ferry them high and low to explore this corner of the country. And when they headed back west, we’d tail them for a day or two, touring Buffalo and Niagara Falls.

But I had another task at hand.

As per a challenge by Christina, my job this week and a half — whether at home around a makeshift fire pit, on the shores of Lake Ontario, in Clayton at Wood Boat Brewery, on a ferry to Dark Island to tour Singer Castle, in the Berkshires or in downtown Buffalo — is to keep Ryan’s hands full of beer and to curate a selection that will both suit his tastes and subtly broaden his horizons.

If the 413 was my only swing, I’d look like Joey Gallo’s first few weeks with the Yankees, walking back to the dugout after a windmilling whiff.

But I took a lot of swings that week, and more than a few of them connected. So while Ryan and Angela kept a steady stream of Bud Light going in and out of refrigerators from here to Niagara Falls, I hit on enough first-time tastes, from locals to regionals to macro Canadians that I had a better week than the Yankees’ new windmill of an outfielder.

I started by stocking the fridge with beers that would swim in some of the same waters as Ryan’s preferred light lager. Light in both ABV and taste profile.

We went about this pretty slowly.

I handed Ryan a tall can of Crisp Trees (Beer Tree Brew Co., Port Crane) when he asked for Bud the first night while hanging out on the back patio. Trees is a crisp 4.5% pilsner a just a touch stronger than the standby but with a crisper, lighter taste ... none of that kind of dry funk that you get on the finish with a Bud Light. He liked it well enough and even had another. So that was a start.

We kept things pretty light the next day on a boat trip to Singer Castle. We might have been the only people drinking on a boat that was more packed than I prefer. But it was a scorching, sunny day right out on the St. Lawrence and we sat on the top deck rather than inside for fresher air and safety for the kids. There was only so much sunshine and so many bad jokes we could take peppered into the history lesson before it became necessary. Canadians were the cheapest thing on tap, so we kept plastic cups of Molson and Labatt Blue Light coming. Ryan’s immediate reaction to both was to say he preferred Molson. It was more “full bodied,” in his estimation.

While Molson isn’t exactly a titan of flavor, at 5% it was stronger than his usual stuff and a bit more bitter. So even on a hot day, he was open to trying something a little stronger. I can work with that.

We all had dinner that night at Wood Boat Brewery in Clayton, probably the first time Christina and I took the boys out to eat in some time. And while Christina and Angela split a bottle (or two?) of wine, Ryan and I dove into the beer. I ordered consecutive flights, and I hit most of Wood Boat’s tent poles after not having been there in more than a year and a half. And it was all really good. But the highlight was the Chocolate Cherry Porter. It was strong at 7.8% ABV, and it had a sweetness to it in the chocolatey finish. But as robust as it was, it was also really smooth and malty. It was a heavy beer for a hot night (I’m seldom glad for a small glass), but it was a welcome feeling to try something new at Wood Boat after so long.

I wasn’t going to try to sell Ryan on something that big and broad right away, so I advised him to get the Lyman Light Ale (5.2% ABV). The easy drinking blonde was so good, a relief from the humid night that he even had another. I was well on track.

So even if he didn’t care for the 413 in Pittsfield, he was broadening his horizons.

Over the course of our vacation, from the Berkshires to the shores of Lake Ontario and to out west to Buffalo and Niagara Falls (cliche, but, hey, they’re tourists), he tried and liked a pretty fair sampling of what the region had to offer.

There were cans of Hoosac Tunnel Amber Ale (Berkshire Brewing Company, South Deerfield, Mass.), a deep copper amber at 6.3% and 23 IBU, on the beach at Westcott Beach State Park and tall boys of Hazelton Hero (War Horse Brewing Company, Geneva) over the tail end of a Yanks-Sox game in my living room, both of which were a hit.

And while he couldn’t really get into Morning Sun, a delightful tangerine wheat from Meier’s Creek Brewing Company in Cazenovia, both Ryan and Angela enjoyed tall cans of Big Elm’s American Ale at the beach and around the that makeshift fire pit.

We poured tall bottles of the Maine Brewing Company’s (pride of Freeport, Maine) Lunch — a 7% IPA that was a little too strong for either Angela or Ryan but that Christina and I gladly split in a hotel in downtown Buffalo, while Raquette River’s (Tupper Lake) Light Lager, a new one for me, was a favorite for the beach and hanging out after the kids were asleep.

And Ryan surprised me by being pretty game. I stayed away from the real hard stuff, because I didn’t think it would suit him. But every time I offered him something, he tried it. And more often than not (I’m glad Angela finished the 413, because I’d have felt weird swiping it or wasting it), he drank it.

Even if “it smells like soap,” like he proclaimed about the Morning Sun, he met every challenge.

And on the last night of our trip, Ryan and I snuck away to ostensibly pick up a takeout order of Buffalo wings from a sports bar across the street from our hotel. But we left earlier than we needed to, unknowingly (at least I’ll tell myself that) leaving the ladies with the sleeping boys and the apparently too-wired-to-sleep 7-year-old.

And we had a few beers. I hadn’t been to a bar in way too long, and it was good to stake out a table, watch some baseball and drink a few.

Ryan shocked me by ordering a pint of Hayburner (Big Ditch Brewing Company, Buffalo), an American IPA that clocked in at 7.2%, easily the strongest beer he’d had that week.

An American ale heavy on the citrus notes of grapefruit, orange and melon, Hayburner was just the right amount of juicy and sweet to cut out some of the bitter, hoppy finish that typically turned him off about IPAs. This was a hit. A big one.

The guy didn’t just like the beer. He loved it. He ordered two of them. When we came back to fix a mistaken wings order (oh, Christina and Angela must have loved that), he had another one.

At the end of a zig zagging trip and with a long drive ahead of him in the morning (maybe three of those was a bad idea), I think I got him hooked.

“Next time we’ll come to Missouri,” I told him. “You can show me some of the beers around Springfield.”

“Hell yeah, man,” he said. “I know a few places.”

Follow Dennis O’Brien on Instagram @beernerddennis.

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