“Have you ever met something that you were going to be eating?” Jeremy House asks me shortly after I arrive at Meadow Haven Farm in Sheffield, Illinois, two and a half hours west of Chicago, on the last really warm day in October.

House, a sturdy 40-year-old with thick arms and callused hands, and his wife, Cherie, have been handling day-to-day operations on these 200 pastoral acres since 2007, when they partnered with the original owners. Meadow Haven is a certified organic farm known for its pasture-raised pork and grass-fed beef, which it sells at places such as Lincoln Park’s Green City Market.

But I’m here to get up close and personal with one of their turkeys.

This Christmas is going to be a pretty big deal at the O’Connor house. Having moved from a cramped condo in Wicker Park into a house in Humboldt Park, we’re hosting our first Christmas dinner. It was time: Ever since I got married, my holidays have been a real-life version of the Vince Vaughn movie Four Christmases. The two-day orgy usually begins with a schlep to my in-laws’ house in Glen Ellyn for a traditional Polish Christmas Eve supper featuring fish and homemade blintzes. Then it’s off to my cousins’ in Elmwood Park for an Italian-style Feast of the Seven Fishes, where we stuff ourselves with smelt, clams, and pasta before gathering around for a wine-fueled rendition of Billy Joel’s “Piano Man.” On Christmas Day, we run out the door for brunch back at my in-laws before sitting down to a huge afternoon meal at my parents’ townhouse in Downers Grove.

But this year will be different. I will stay in my footie jammies the entire day. The relatives are coming to us.

This changing of the guard inspired me to jump-start a new tradition. This isn’t a Butterball occasion. Instead, I decided to purchase a holiday bird fresh from the farm and smoke it on the grill while consuming a steady stream of Moscow mules. In fact, I wanted to go the extra mile and pick out the turkey myself before it was butchered. But when I tell my family my plan the night before my trip to Meadow Haven, it’s clear that I’m the only one excited about going full-bore farm-to-table.

“Blech!” yells seven-year-old Josephine. “I’m not gonna eat it. It sounds disgusting.” I explain that it’s good to know where food comes from and, in this case, to remind ourselves it used to be a live animal. She is not swayed.

“I’m still not going to eat it,” she says, pausing for effect. “Because it’s disgusting.”

“We’re more Whole Foods–to–table people,” adds my wife.

Undeterred by my family’s lack of enthusiasm, I join House on a morning walk to visit his 350-plus gobblers. Within minutes of crossing the electric fence that protects them from Bureau County’s sizable coyote population, we’re surrounded by a gaggle of squawking white-feathered beasts whose strutting reminds me of the velociraptors from Jurassic Park. I reach down to pet one, and it darts off. Then they all turn and flock away in unison. Some seek shade under the open-air A-frame enclosure; others nibble the grass. So this is what free-range looks like.

On its website, Meadow Haven offers an open invitation to “meet your meat.” But it seems I’m the first to request a face-to-face interaction. “Most people come here to make a connection with the farm and their farmer,” House says. “Not many are interested in connecting with an individual animal.”

Standing among these happily frolicking turkeys, I start to question whether this was a good idea. What if I become attached to the critter? If I met that cute pig from the movie Babe, could I shove him into my slow cooker?

It’s obvious that House has a deep affinity for the birds. Every year, he cares for them from cradle to grave. They were only 8 days old when they arrived in July from the hatchery. House could hold them in the palm of his hand.

While I ponder this existential dilemma, he puts me to work. We walk toward the barn, hop on his tractor, and pull a red-and-yellow feed grinder over to a metal bin. We place big buckets of feed in the field, and the turkeys come running. As they chow down, House pulls out a heavy rubber band. He’s ready to tag the leg of my dinner bird. I scan the selection and spot a tom (a.k.a. a male) lingering near a feed bucket like he owns the place.

Something about this particular turkey grabs me. He looks scrappy. He’s got some dirt on his feathers. I notice him puffing out his red neck, trying to snag the attention of the hens. By December, House says, this 15-pound gobbling gigolo should be just the right size to feed my 10 guests. “I can’t tell how big each will get,” House tells me, “but this will be good enough turkey that you’ll be thankful to have leftovers.”

House emits a series of bloodcurdling calls to get the tom’s attention and then grabs the bird by the legs, avoiding his sharp talons. The turkey’s wings flail for a few seconds before he calms down.

I name him Mr. Biscuits, in honor of the plucky fowl, Biscuits, that President George W. Bush pardoned prior to Thanksgiving 2004. But my Mr. Biscuits will not elude his fate. In a few weeks, he and his pen pals will be “harvested”—a farm-friendly euphemism for “slaughtered.” Being the coward that I am, I won’t carry out the act myself. Even House isn’t crazy about murdering his birds; he outsources the processing.

As I stare into Mr. Biscuits’ almond-shaped eyes, it’s tough not to feel the figurative blood on my hands. My goal was to establish a new tradition and help my daughters better understand the food chain. But when I sit down to carve Mr. Biscuits’ scrumptious meat, I’ll have a hard time shaking the vision of this cool turkey in his prime, pimping for the ladies on a pristine fall day.

After the tour, House grills up a few pork shoulder steaks from his well-stocked walk-in fridge. A few months ago, these hunks of meat were living the good life in the muddy pen across from the turkeys. I take one bite of the juicy pork and fully appreciate that they lived for a higher purpose: to be eaten by me. As Jeanne, the farm’s co-owner, told me a few hours earlier, every day is a good day for their animals. Except, of course, one.

“So when can I pick up my turkey?” I ask. I know Mr. Biscuits would have wanted it this way.