Bruce Sherman knows how to put on a show, which he has been doing to great acclaim for more than a decade at North Pond, the romantic Arts and Crafts hideaway in Lincoln Park. Earlier this year, he won the coveted James Beard award for best chef in the Great Lakes region, an honor that validates the durable appeal of his way of cooking: seasonal foodstuffs—local produce, artisanal meats, sustainable seafood—shined up with classical French technique.

But Sherman, 51, is also a husband and father of two (Emma, 17, and Kate, 11). And the last thing he wants to tackle on a day off is a complicated culinary project. When he and his wife, Joan, invite family and friends to their Evanston home, they generally keep things simple. For example, Sherman will make homey braised lamb shanks and winter spinach for Hanukkah with his dad, who lives in the city. For Christmas, which the Sherman family celebrates too, he’ll serve up hot-pressed panini—stuffed with prosciutto, pickled red peppers, and Wisconsin cheese—and a bottomless bowl of Chex mix. “That’s our tradition because everyone’s exhausted from getting up early and opening presents,” Sherman explains.

So he seemed like the perfect person to solve the stressful mind game that holiday entertaining can become: Should you try something new and exciting or satisfy the tradition-bound expectations of your guests? Besides that, how is it possible to cook everything from scratch without losing it?

At Chicago’s request, Sherman created a menu that kicks the usual festive dinner fare up a notch but is easy enough for the average person to manage in a regular home kitchen. No fussy ingredients. No recipes within recipes. The result is a tour de force: a sophisticated cocktail and appetizer pairing, a dramatic pork rib roast with a blizzard of hearty side dishes, and an elegant dessert that tastes positively restaurant-worthy.

His secret? Choose dishes that you can prepare largely in advance. Study his detailed game plan and you’ll see that it is possible to make a big, impressive meal with a relatively small amount of cooking on the day of the event—leaving you plenty of time to plump the pillows, sip a test cocktail, and catch your breath before the doorbell rings. “If something is so stressful that you can’t have fun, what’s the point?” Sherman says.

Just as important, he adds, is to buy the best-quality ingredients you can find. Anyone can set out a bowl of olives. But when you buy the freshest, brightest green Cerignola olives around (one good source for them is Graziano’s, at 901 West Randolph Street), half your work is done even before you marinate them overnight.

One of the first chefs to champion the Green City Market (the 12-year-old farmers’ market in Lincoln Park; held Saturdays in winter at the Peggy Notebaert Nature Museum), Sherman argues that a carrot is not always a carrot. Indeed, when I tested his recipe for balsamic-roasted root vegetables, baby carrots from the farmers’ market held up far better in cooking than did the organic carrots from the supermarket, retaining their crispness even after 40 minutes in a hot oven.

Finally, Sherman counsels, let go of the idea that you must make absolutely everything from scratch. In other words, give yourself permission to make strategic timesaving substitutions. Take the crust for his rack of pork, a clever twist on the traditional Christmas ham. Instead of using the gingersnaps from Sherman’s recipe, feel free to go with ready-made cookies, he says, so long as you eschew bland varieties for good ones with real spices, either from a bakery or the grocery store.

As for his silky-smooth bourbon applesauce: It couldn’t be easier to make. In a pinch, though, simply add a splash of nice bourbon (Sherman likes Rowan’s Creek) to a good-quality applesauce and warm it gently before serving. Don’t forget to set aside a booze-free portion for the kids.

And you can prepare the components of the dessert— poached pears served with a rosemary-flavored custard and delicate orange-almond tuiles on the side—in advance. Or skip the sauce and cookies and match the pears with either of these two supereasy accompaniments: a scoop of eggnog ice cream (plain vanilla works, too) or a soft cheese that becomes custard-like at room temperature. Sherman recommends procuring a wheel of Rush Creek Reserve, a glorious bit of aged raw cow’s milk from the Uplands Cheese Company in Dodgeville, Wisconsin. (Be sure to reserve one in advance from Pastoral, at 53 East Lake Street, or Provenance Food and Wine, at 2312 West Leland Avenue, because every week’s supply of this limited-release cheese reliably sells out.) “You could even dip the gingersnaps into it,” Sherman muses. “It’s just magical.”

He’s talking about the cheese. But chances are you’ll feel that way about the whole evening.

Bruce Sherman's Holiday Menu

Meyer Lemon Daiquiris

Makes 1. A seasonal twist on the classic Cuban cocktail.

1 oz. tropical white rum (such as Barbancourt or Koloa)
1 oz. Lillet Blanc
1 oz. Meyer lemon juice (reserve peels for garnish)
1 Tbsp. honey syrup*

*HONEY SYRUP: Dilute ¼ cup orange blossom honey with 2 Tbsp. boiling water.

Combine rum, Lillet, lemon juice, and honey syrup in shaker. Fill with ice. Shake and strain into a stemmed glass. Twist the peel over the drink, rub it on the rim, and float it on the surface of the drink.

Smoked Trout Canapés

Makes 30. Champagne gelée adds sparkle to this elegant one-bite appetizer without much effort.

Trout mousse
8 oz. cream cheese, softened
Zest and juice from ½ lemon
8 oz. smoked trout, flaked
1 Tbsp. minced chives
1 Tbsp. chopped mint
Salt, white pepper, and Tabasco

Champagne gelée
1 ¼-oz. package powdered gelatin
1 cup medium-dry Champagne or Cava plus 2 Tbsp.

Assembly and garnish
1 satsuma mandarin orange
Sliced pumpernickel bread, cut into 1½" circles or squares, brushed with oil, seasoned with salt and pepper, and lightly toasted
Pistachios, shelled and toasted

TROUT MOUSSE: Using an electric mixer, beat cream cheese with lemon zest and juice until smooth, about 10 minutes. With a spoon, mix in trout. Add herbs, salt, and pepper to taste and a dash of Tabasco; stir until incorporated.
Do ahead: Up to 5 days in advance.

GELÉE: Mix powdered gelatin with 2 Tbsp. of Champagne and let rest for 5 minutes. Gently heat ½ cup of Champagne (high heat will flatten the effervescence) and, off heat, add to the gelatin. Stir carefully to dissolve. Add remaining ½ cup cold Champagne. Pour through a fine mesh strainer into a small bowl or shallow dish and refrigerate until firm, at least 6 hours.
Do ahead: Up to 3 days in advance.

ASSEMBLY: Peel orange with a knife, eliminating all skin and pith, and remove segments; drain on a paper towel and set aside. Turn out gelée on a cutting board and roughly chop. Using a fork or small spatula, place a scant tablespoon of trout mousse on the pumpernickel round. Garnish the top with an orange segment, gelée, a pistachio, and a chive tip.

Olives with Fennel and Citrus

Makes 1 quart. These bright green Italian olives are lightly brined and almost meaty in texture.

2½ lb. Cerignola olives with pits, strained
1 bulb fennel, halved, cored, and cut into ⅛"-thick slices
cup good-quality extra virgin olive oil
Zest and juice from ½ orange
1½ tsp. red chili flakes
2 tsp. salt
Freshly ground white pepper

In a large container, mix all ingredients and let marinate in the refrigerator 12–48 hours, tossing occasionally. Let come to room temperature before serving, about 1 hour.

Gingersnap-Crusted Rack of Pork

Makes 8–10 servings. Lighter than prime rib, this roasted rack of pork is just as impressive.

1 8-rib bone-in Berkshire pork loin (about 4–5 lb.; have a butcher trim the roast, remove the chine bone, and French the rib bones)
½ cup rock salt (can substitute ¼ cup kosher salt)
1 tsp. pepper
½ cup brown sugar
2 Tbsp. vegetable oil
1 large egg white
¼ cup maple syrup
¼ cup Dijon mustard
2 cups crushed gingersnaps

SPECIAL EQUIPMENT: An instant-read thermometer

The night before, cure the pork: Mix salt, pepper, and brown sugar; liberally rub the mixture over the pork. Set meat in a pan on rack, cover, and refrigerate for 12–15 hours. (If using kosher salt, cure for 6–8 hours.) Bring meat to room temperature, about 1 hour.

Preheat oven to 450°F. Brush the salt-and-sugar mixture off the pork. Dry the meat with paper towels, and brush with a light coat of oil. Wrap bones with aluminum foil. Place on rack, bones pointing up, and roast about 20 minutes. Rotate the pan and turn down the heat to 300°F; roast until the internal temperature reaches 135°F, about 30–45 minutes. Let rest for 30 minutes.

Heat oven to 350°F. Beat egg white until foamy and combine with maple syrup and mustard. Brush the mixture liberally over the meat. Place gingersnaps in a sealable plastic bag and crush to an even crumb with a rolling pin. Transfer the roast to a cutting board or work surface and press a generous coating of gingersnap crumbs evenly on the surface of the meat, including the underside but not the ends. Bake until lightly browned, 10 minutes. Carve the roast into 1" slices, a bone per person.

Cider-Braised Wild Mushrooms

Makes 8 servings. These mushrooms develop a rich jus that acts like a sauce. The surprise ingredient? Cinnamon.

2 Tbsp. vegetable oil
1 lb. chanterelle, black trumpet, and hedgehog mushrooms, trimmed and washed
1 lb. button mushrooms, trimmed and washed
2 tsp. salt
Freshly ground white pepper
¼ cup minced shallots
4 cloves garlic, peeled and lightly crushed
½ cup Calvados
½ cup apple cider
1½ cups chicken or vegetable stock
1½ tsp. ground cinnamon
4 Tbsp. cold butter, cubed
½ cup diced tomatoes (optional)
2 Tbsp. minced chives

In a large skillet over medium-high heat, heat oil and swirl to evenly coat the pan. Add mushrooms and toss with salt and pepper. (You can also use two skillets or cook mushrooms in batches.) Cook until mushrooms release their liquid, about 2 minutes, and then continue to cook until the liquid evaporates. Add shallots and garlic and cook until shallots soften, 2 minutes.

Add Calvados and reduce to dry. Add cider, stock, and cinnamon; bring to a boil, then simmer until the liquid reduces to a ½ cup. Stir in butter, letting it gradually melt to emulsify. Remove garlic and season with salt and pepper. Off the heat, stir in tomatoes and garnish with chives.
Do ahead: Up to 2 days ahead (omit the tomatoes and chives); cover and chill. Reheat and garnish before serving.

Bourbon Applesauce

Makes 6 cups. Velvety smooth, this classic pairing with pork adds a bright note—with a smoky kick.

Juice of 1 lemon
3 lb. firm tart apples (such as Golden Delicious or Mutsu)
cup smoky bourbon (such as Rowan’s Creek)
2 Tbsp. butter
3 Tbsp. honey

In a large bowl, add lemon juice to 2 qt. of water. Peel and core apples and cut into ½" cubes, dropping into lemon water as you go. Strain apples. In a heavy-bottomed nonreactive saucepan, combine apples with the rest of the ingredients. Cut a circle of parchment paper and press on the surface of the apples to prevent oxidation. Cook over low heat until soft, stirring often, about 45 minutes. Using a blender, purée until very smooth. Pass through fine strainer, if desired. Add honey to taste. Serve warm.
Do ahead: Up to 5 days ahead; cover and chill.

Joan’s Favorite Squash Gratin

Makes 12 servings. Kabocha, a Japanese winter squash with a hard rind, gives this gratin an uncommonly creamy texture.

3 cloves garlic, crushed
2 Tbsp. butter, softened
2 cups heavy cream
½ cup maple syrup
2 Tbsp. salt
½ cup minced chives
1 green kabocha squash, about 4–6 lb. (can substitute a 2½-lb. butternut squash; you should have 2 lb. of either squash after removing rind)
2 lb. garnet yams, peeled
2 lb. russet potatoes, peeled
6 oz. Gruyère-style cheese, grated

Preheat oven to 350°F. Rub garlic on the inside of the gratin dish; discard. Rub butter on interior. In a large bowl, mix cream, maple syrup, salt, and chives. Cut squash, yams, and potatoes into ⅛" slices and place in cream mix. Mix in cheese. Place squash-potato mix in gratin dish, making sure pieces lie flat. Pour excess liquid over top and press down to submerge. Bake for 30 minutes. Rotate pan and cook until lightly browned and a knife inserted in the center meets no resistance, about 30 minutes more. Let rest 15–30 minutes before serving.

Brussels Sprouts with Bacon and Hazelnuts

Makes 8 servings. Instead of roasting Brussels sprouts, Sherman blanches the leaves only and tosses them in sizzling bacon fat.

2 lb. large Brussels sprouts, green leaves only (about 8–10 cups)
4–6 oz. thick-sliced smoked bacon (look for ¼" slices)
2 tsp. vegetable oil
1 Tbsp. lemon juice
Salt and pepper
4 oz. toasted hazelnuts, halved

Separate sprouts into individual leaves by progressively cutting off stem and peeling off leaves. (Reserve cores for another use.) In a large pot, boil water that has been generously salted (about 1 Tbsp. salt per quart). Blanch leaves, about 2 minutes, and transfer immediately to a bowl of ice water. Drain and dry in a single layer.
Do ahead: Make a day ahead. Store in a sealable plastic bag and chill.

Cut bacon crosswise into ¼" strips. In a heavy-bottomed skillet, heat oil over medium heat and cook bacon until browned, about 3–5 minutes. Remove bacon with slotted spoon and set aside. Pour off about half of the rendered fat. Over high heat, toss the leaves to coat and sauté until hot, about 2–3 minutes. Add lemon juice and season with salt and pepper. Transfer to a serving bowl and garnish with reserved bacon and nuts.

Balsamic-Roasted Root Vegetables

Makes 10 servings. Sherman roasts the onions and garlic cloves in their skins. Remove the jackets before serving—or let guests open them at the table.

2 lb. baby red beets, trimmed and washed
2 lb. baby carrots, trimmed and scrubbed
2 lb. cipollini onions, unpeeled
16 cloves garlic, unpeeled
12 sprigs sage (optional)
cup olive oil
3 Tbsp. good-quality balsamic vinegar
Salt and pepper

Preheat oven to 400°F. In a large bowl, toss the beets, carrots, onions, garlic, and sage with olive oil, vinegar, salt, and pepper. Pick out the beets and wrap in foil. Place on a pan and roast. After 20 minutes, add the rest of the vegetables, placing them on a separate foil-lined baking sheet. Arrange the carrots, onions, garlic, and sage in a single layer; cover with foil and add to oven. (If you separate the vegetables by type, you can remove them in groups as they finish cooking.)

After 20 more minutes, unwrap the beets and remove the foil from the vegetables. Continue roasting until all the vegetables are cooked through but still firm and the beets are easily pierced with a skewer, about 15 more minutes. Combine vegetables in a serving bowl and season to taste.

Cassis-Poached Pears with Rosemary Crème Anglaise and Orange-Almond Tuiles

Makes 8–12 servings. The pears benefit from a prolonged soak in spiced wine.

1 750-ml bottle full-bodied red wine, such as cabernet or merlot
1½ cups crème de cassis
1½ cups ruby port
cup granulated sugar
3 sticks cinnamon, broken in halves
1 Tbsp. fennel seeds
1 Tbsp. black peppercorns
2 pieces star anise
Juice from 1 lemon
8–12 small ripe Bartlett or Bosc pears

Crème Anglaise
¼ cup roughly chopped fresh rosemary, leaves only
1 cup whole milk
1 cup heavy cream
1 vanilla bean or 1 tsp. vanilla extract
cup granulated sugar
6 large egg yolks

1 cup slivered raw almonds
cup granulated sugar
¼ cup fresh orange juice
¼ cup all-purpose flour, sifted
2 Tbsp. butter, melted
½ cup corn syrup

PEARS: Bring red wine, crème de cassis, and port to a boil; add sugar and all the spices. Lower heat and barely simmer for 2–3 hours. Strain, cool, and refrigerate.
Do ahead: Make the spiced wine up to 2 weeks in advance.

In a bowl, mix the lemon juice with water; peel pears and drop into the lemon water to prevent oxidation as you work. Core each pear through the bottom with a melon baller, being careful to retain the shape of the fruit. In a large saucepan, combine the whole pears and the spiced wine and slowly bring to a gentle simmer until cooked through, about 30–45 minutes. Cover the pears with a circle of parchment paper as they simmer to prevent oxidation. Cool in liquid, then refrigerate. Make at least 2 days in advance so pears can fully absorb the poaching liquid.
Do ahead: Up to 7 days in advance.

CRÈME ANGLAISE: Place rosemary leaves in a bowl set in another bowl of ice; reserve. Combine milk, cream, vanilla, and half of the sugar in a small saucepan and bring to a boil over medium heat. Whisk together yolks and remaining sugar in a separate bowl until the mixture thickens and becomes pale yellow. When the milk boils, pour it in a thin stream into the egg mixture, whisking continuously. Transfer the mixture back into the saucepan and cook over low heat, stirring with a wooden spoon until it thickens enough to coat the back of the spoon (you’ll be able to draw a line through the sauce with your finger; alternatively, cook until the temperature reaches 185°F). Immediately pour sauce through a fine mesh strainer into the bowl with rosemary and stir to cool. Cover and chill 4–6 hours. Strain out rosemary and keep the sauce refrigerated until serving.
Do ahead: Up to 2 days in advance.

TUILES: In a food processor, pulse together the almonds and sugar until roughly chopped. Transfer to an electric mixer and add remaining ingredients, one by one, until just incorporated. Make the batter at least 1 day before you bake the tuiles.
Do ahead: Up to 1 week in advance. Cover and chill.

Preheat oven to 375°F. Stir batter well and, using a teaspoon, drop batter in mounds 4" apart on a baking sheet lined with parchment or a nonstick silicone mat. Bake until deep golden brown, about 5–6 minutes. (The cookies will spread while baking.) Let cool until cookies are firm but still pliable, about 1 minute. Working quickly with a spatula, drape each cookie over a glass set on a kitchen towel (to prevent rolling) or around a dowel until set, about 1 minute. (If cookies become brittle, warm briefly in the oven to soften and try again. Alternatively, serve these cookies as flat rounds.) Cool completely before storing in an airtight container.
Do ahead: Up to 2 days in advance.

ASSEMBLY: Ladle a shallow pool of crème anglaise into a dessert bowl and set the pear upright into the sauce. Garnish with a tuile.

Iced Gingersnaps

Makes 48. The traditional Christmas cookie, made from scratch. Set aside half the batch for the pork’s crust, and ice the rest.

1¾ cups all-purpose flour
1 tsp. baking powder
2 Tbsp. ground ginger
1 tsp. cinnamon
1 tsp. salt
½ tsp. ground cloves
½ tsp. ground black pepper
cup butter, softened
¾ cup granulated sugar plus ¼ cup for sprinkling
1 large egg
¼ cup blackstrap molasses
2 tsp. lemon juice

1 cup confectioner’s sugar
1 large egg white
1 tsp. lemon juice

COOKIES: In a small bowl, sift together flour, baking powder, ginger, cinnamon, salt, cloves, and pepper. Using an electric mixer, beat butter with sugar in a large bowl until light and fluffy, 2–3 minutes. Beat in egg, then molasses and lemon juice. Fold in dry ingredients until just incorporated. Chill the dough until firm, or overnight.
Do ahead: Make dough up to 7 days in advance.

Preheat oven to 350°F. Line a cookie sheet with parchment or a nonstick silicone mat. Drop rounded teaspoons of dough 1½" apart. Bake until partially melted, about 5 minutes, and remove from oven. Sprinkle granulated sugar over each cookie and gently flatten with the bottom of a ramekin or glass. Return to oven and bake until slightly puffed and a shade darker, about 8 minutes. Transfer cookies to a rack to cool completely.

ICING: Whisk together all ingredients and let stand for 5 minutes. Drizzle over cooled cookies. with a spoon.

Photography: Clayton Hauck; Styling: Johanna Lowe