Ale Street News Online

It’s not every day that a girl gets to wash down a 4-course dinner with seven shots of bourbon — all while sitting next to the guy whose name is on the whiskey’s label. That opportunity presented itself to me recently when the Federalist, a swanky restaurant in Boston’s Beacon Hill neighborhood, held its first bourbon dinner.

Known for its wine dinners, the Federalist branched out to include spirits early this year with its first single-malt Scotch dinner. The night was a hit. The bar manager, a handsome Croatian named Srjan "Serge" Bajas, said that a few customers, excited by the concept of whiskey and fine food, approached him asking, "When are you going to have a bourbon dinner?"

A few months later, there we were, a smallish but enthusiastic group of about 20, gathered for dinner in the restaurant’s wine cellar, where special events are held. This cellar is one of Boston’s best dining spots. It’s more intimate than the main dining room, and more interesting, too: the wine list is as thick as a Russian novel and features stuff like "a 1907 Heidsieck Monopole [Champagne], rescued from a schooner sunk by a German U-boat," says the Fed’s website. The bottles sit behind a thick, glass wall like crown jewels, lending an aura of history to the room.

The liquid part of the dinner consisted of six bourbons and one rye from the Old Rip Van Winkle distillery in Frankfort, KY. (As of 2002, Van Winkle bourbons are produced under a joint venture with the Buffalo Trace distillery.) The youngest of them were 10 years old, the oldest, 23. Whiskey connoisseurs hold these bourbons in near mystical regard for their complexity and other-worldly smoothness. The Beverage Tasting Institute recently gave Pappy Van Winkle’s Family Reserve 20 Year a score of 99 — its highest-ever rating for a bourbon.

Ever had a 20-year-old bourbon? Neither had I. In fact, I had never heard of Old Rip Van Winkle, let alone tasted it. When it comes to bourbon, my experience with what you’d call the good stuff has been limited to taking the occasional nip from my boyfriend’s stash of Knob Creek or Baker’s.

Julian P. Van Winkle III, the third generation to carry on his family’s whiskey-making tradition, was on hand to discuss his bourbons. Before I met the guy, I pictured someone who looked like Julian’s grandfather, Julian "Pappy" Van Winkle — the white-whiskered, cigar-smoking figure who appears on some of the labels — and who had an eccentric manner. The third Julian is instead a clean-shaven, "regular guy" with a low-key manner and a dry wit.

"You don’t want to swirl the bourbon around in your glass. That’ll just kick up the fumes from the alcohol. If you want to smell bourbon, you kind of have to sneak up on it," he said.

The first bourbon in the lineup was the distillery’s "basic" offering: Old Rip Van Winkle 10 year, 90 proof. It was one of the most complex, supple spirits I’d ever tasted. If this is where we’re starting, I thought, I’m in for a memorable night. The primary "small" grain — the grain other than corn — in Van Winkle bourbon is wheat, which is said to impart a delicate sweetness and a distinct smoothness as the bourbon ages. That smoothness also comes from the fact that Van Winkle mellows in its charred white oak barrels for at least 10 years, compared to four to eight years for most bourbons.

As we made our way through the second 10 Year (this one at 107, or barrel, proof), the 12 Year (90.4 proof), the 15 Year (107 proof), and the 20 Year (90.4 proof), I marveled at how each successive bourbon was more velvety and deeper in flavor than the one that preceded it. The 23 Year was the only one that didn’t live up to my expectations. Maybe my taste buds were shot, or maybe this bourbon really was delivering diminishing returns at this advanced age. At around 25 years, said Julian, the wood flavor starts to take over.

Somewhere in the middle came the delicious 13 Year Reserve Rye, which, I have to admit, was the bottle I most wanted to take home with me. It offered a drier, more peppery contrast to the caramel and vanilla flavors of the bourbon. Julian called it a "cigar-smoking whiskey," and added that it’s the distillery’s bestselling export to London — "Scotch drinkers like it."

The Federalist’s executive chef, David Daniels, did a great job pairing dishes with these strong spirits. Beef carpaccio with pecorino panna cotta, miso-glazed Atlantic halibut, tenderloin Beef Wellington in thyme madeira sauce, and rich chocolate cake with raspberry mousse escalated in flavor and texture as the bourbon got older and more complex.