I own a grill that I use enthusiastically for four months and then guiltily ignore, and Labor Day is the weekend I make peace with that. It is the last cookout of the season for most of us, which puts a pressure on it that a random Saturday in July never has.
So this is built around food that can be cooked in waves rather than all at once, plus sides that were made yesterday and are now just sitting in the fridge being cold and good. Get those sides done the day before, which is the step most people skip and then they spend the whole afternoon inside instead of out where the party is.
1) Burgers on the Grill

Make the patties wider than the bun and press a dimple into the center of each, because they swell as they cook and a dome-shaped burger slides right off the bread. Salt the outside only, right before they hit the grate; salt worked into the meat makes the texture springy and strange. Flip once. Every extra flip is another chance to press out the juice that makes a burger worth eating.
2) Smash Burger Sliders

These want a flat surface rather than grates, so a cast iron pan set right on the grill is the move. Smash them hard for the first ten seconds and then never again, since the crust forms in that moment and pressing later only squeezes it dry. About ninety seconds a side. Twelve sliders feed more people than six burgers and cost roughly half as much.
3) Baby Back Ribs

Pull the membrane off the back of the rack before anything else, because it never renders and it blocks the rub from reaching the meat. Low and slow at 275°F (135°C) for about three hours, wrapped in foil for the middle hour. Sauce goes on in the last fifteen minutes only, since any earlier and the sugar burns black. This is the one thing here worth starting in the morning.
4) BBQ Pork on the Grill

Indirect heat first and direct heat last, which is the general rule for anything thicker than an inch. A pork shoulder can go on before anyone arrives and be pulled apart as they show up. Rest it a full twenty minutes before shredding. That part is non-negotiable, because pork shredded straight off the grill leaves all its juice on the board.
5) Pulled Pork with Toppings

Set out the pork, the buns, the slaw, the pickles, and the sauce, then walk away and let people build their own. It is the lowest-effort way to feed a crowd and it always reads as more generous than a plated meal. Keep the pork sitting in a little of its own cooking liquid over low heat so it does not dry out across an afternoon. Two sauces, one vinegar and one sweet, and the argument settles itself.
6) BBQ Chicken Sandwiches

Thighs rather than breasts, because a breast goes from done to dry in roughly two minutes on a grill. Sauce them at the very end and then again once they are on the bun. Toast the cut sides of the buns on the grate for thirty seconds, which sounds fussy and is the whole difference between a sandwich and a soggy one. Cheaper per person than almost anything else on this list.
7) Grilled Chicken Thighs

Skin side down over medium heat, then leave it alone for eight full minutes and resist every urge to move it. Moving it early is exactly why skin tears and sticks to the grate. The fat needs time to render out and crisp, so a hotter grill is not a faster grill here. About $1.50 a serving and the most forgiving protein you can put over fire.
8) Grilled Skirt Steak

Skirt steak wants very high heat and very little time, three minutes a side and not a moment more. It is thin enough that the interior overshoots almost the instant the exterior is right. Slice it against the grain, which on skirt means across the short dimension, and that alone is the difference between tender and chewy. Marinate it in the morning and it is dinner in eight minutes.
9) Grilled Flank Steak

Score it lightly in a diamond pattern before marinating so the marinade reaches past the surface. Flank feeds a crowd for a fraction of what the nicer cuts cost, roughly $10 a pound against triple that for ribeye. Medium rare or nothing, because flank cooked past that turns to rope. Rest it ten minutes and slice it thin on a hard angle.
10) Tri Tip Sliders

Tri tip is a west coast cut that deserves to be everywhere, and piled onto slider buns it feeds roughly twice the people that slicing it onto plates does. Sear it hard on both sides, then move it to indirect heat until the center reads 130°F (54°C). The grain changes direction partway along the roast, so cut it in two at the bend and slice each half separately before any of it goes near bread. Almost nobody does this and everybody should.
11) Vegetable Kebabs

Cut everything to the same size or nothing finishes at the same time, which is essentially the entire skill involved. Give each type of vegetable its own skewer instead of alternating them, since peppers and mushrooms cook at completely different rates. Soak wooden skewers for half an hour first. Oil them heavily, because vegetables have no fat of their own to keep them off the grate.
12) Grilled Fish Fillets

A cold grate is the reason fish sticks and tears, so get the grates screaming hot and oiled before anything goes near them. Leave the skin on, cook skin side down for most of the time, and flip once at the very end. Firm fish only on a grill; delicate fillets belong in a pan. A cedar plank makes all of this much easier if the whole idea makes you nervous.
13) Baja Fish Tacos

The fish takes four minutes, which makes this the thing to cook when people are already hungry and hovering. Slaw and crema get made in the morning and are better by the afternoon. Warm the tortillas directly on the grate for fifteen seconds a side. A squeeze of lime does more work here than any other single ingredient.
14) Black Bean Nachos

Nachos belong at the start of a cookout, when the coals are still whitening and everyone is standing around with nothing to do. Build them in a single layer on a sheet pan rather than a pile, because a mountain of nachos is dry on top and soggy underneath. Cheese goes on before any wet topping, always. Four minutes under the broiler, then the cold things after.
15) Grilled Peach Salad

Halve the peaches, oil the cut faces, and grill them face down for four minutes without touching them once. Use peaches that are firm rather than ripe, because a ripe peach collapses on the grate into a sad puddle. Arugula, goat cheese, and a sharp vinaigrette to push back against the sweetness. This is the dish people ask about afterward.
16) Baked Beans

Baked beans are one of the few things that genuinely improve overnight, so make them the day before and reheat. Bacon, molasses, and a long slow oven, with a splash of vinegar at the end to stop the sweetness turning into a wall. They will hold on a low burner all afternoon without any attention at all. Feeds a crowd for a few dollars.
17) Potato Salad

Dress the potatoes while they are still warm so they absorb the vinegar rather than merely wearing it. Then chill it properly, because a mayonnaise salad sitting in the sun for three hours is the classic way to ruin a cookout for everyone present. Keep the bowl nested in ice if it is going to live outside. Make it the day before; it is better on day two.
18) Macaroni Salad

Pasta drinks dressing as it sits, so dress it while slightly warm and then add more right before it goes on the table. Rinse it cold and drain it thoroughly first, or the whole bowl turns watery by the time anyone gets to it. Celery and red onion for crunch and a great deal of black pepper. It costs almost nothing and it always goes.
19) Blue Cheese Coleslaw

Blue cheese in coleslaw sounds like too much and turns out to be exactly right next to anything smoky. Salt the shredded cabbage and let it drain thirty minutes before dressing, which is the step most people skip and then they wonder why the slaw is swimming an hour later. Dress it no more than two hours ahead. Crumble the cheese in at the last possible moment.
20) Cornbread

Preheat the skillet in the oven before the batter goes in, because that sizzle on contact is what gives you the crust around the edge. Use buttermilk and do not substitute, since the acid is doing real work with the leavening. Bake at 425°F (220°C) for about 20 minutes. Serve it in wedges straight out of the pan with honey butter.
21) Creamed Corn

Fresh corn cut off the cob is a genuinely different food from the canned version and it is worth the ten minutes. Scrape the bare cobs with the back of the knife afterward to get the milky liquid, which thickens the whole dish without any extra cream. It reheats well, so this is another candidate for the day before. Late August corn is at both its cheapest and its best.
22) Grilled Potato Wedges

Par-boil the wedges for eight minutes before they go on the grill, or you get charred outsides and raw centers every single time. Toss them in oil while still hot from the water so it soaks in rather than sitting on top. Grill cut side down over medium heat until the marks set, then move them to the cooler side to finish. Better than fries, and there is no pot of oil to deal with afterward.
23) Watermelon and Feta Salad

There is nothing to cook, which by the third hour of a cookout is the most appealing quality a dish can have. Drain the cubed watermelon in a colander for twenty minutes or the bowl fills with juice. Feta, mint, lime, and a hard grind of black pepper. Assemble it right before serving, since this is the one thing here that does not improve with sitting.
24) Grilled Corn on the Cob

Leave the husks on, soak the whole ears in water for fifteen minutes, and grill them husk and all for about twenty minutes. The husk steams the kernels while the outside chars, and peeling it back afterward is half the pleasure of eating it. Pull the silk out before soaking if you have the patience for it. Butter, salt, lime, chili powder, in that order.
25) Grilled Garlic Bread

The order matters here: grill the bread cut side down bare first, then rub a raw garlic clove across the toasted surface, then add the butter. Buttering before grilling just burns the butter and gives you none of the flavor. Ninety seconds, using grill space that is otherwise sitting empty. This is the item people remember.
26) Key Lime Pie

Made entirely the day before, which is the only reason it belongs at a cookout at all. Real key limes are small and fiddly and regular limes are honestly close enough here. The filling sets from the acid rather than the oven, so do not overbake it hunting for firmness. It slices cleanly straight out of a cold fridge.
27) Strawberry Shortcake

Biscuits rather than sponge cake, which is the correct version and I will not be taking questions on it. Macerate the strawberries with a spoonful of sugar two hours ahead so they release their syrup. Whip the cream at the last minute and stop while it is still soft enough to slump. It is the right ending for a summer that is technically over.
