You need room to spread out the Sunday New York Times at brunch.

First things first: if your hotel or condo doesn’t have Sunday papers at the front desk, head over to Carl’s Pharmacy. Paper in hand, settle into the calm expanses of Element 47 or Prospect at the Jerome. Need more elbow room in case you punch the front page? Try the outdoor seating (and quiche Lorraine) at Jour de Fête, or take Upper Crust bagels to the shady picnic table of your choice. Then there’s BB’s, with its classic brunch menu and sun-drenched patio. Take a seat under a big red umbrella, then order a BLT Bloody Mary followed by the fine smoked salmon plate or chilaquiles verde with duck confit and a duck egg. You’ll feel stylish enough for the Styles section.

You desperately want to impress the guy/gal you met hiking on Smuggler.

Be ready to throw down some serious bucks—it’ll be hard to reel in that Aspen catch if you skimp. Then start with the obvious: Matsuhisa and Cache Cache consistently deliver premium experiences for premium prices. A less obvious but just as impressive choice: the Monarch, an upper-crust steak house where the finer things in life include Siberian osetra caviar, an oyster-laden seafood tower, and the Corpse Reviver cocktail. Plus, lots of first-rate beef. Another contender: Casa Tua, where the white tablecloths are thick and soft, and the lighting is set for maximum sex appeal. Book your table upstairs in the private club, where one-week memberships are available. Then enjoy burrata with organic tomatoes, fettuccini with wild mushrooms and black truffles, and beef tenderloin with foie gras. Dessert? You can take it from there.

Veggies are your thing—preferably with a chaser of fresh-pressed juice.

Vegetarians and vegans are lucky creatures here, as summer signals a celebration of Colorado farm bounty. Aspen’s sole meatless eatery is also entirely organic: Spring Café prepares a cornucopia of produce-centric dishes (including pasture-raised eggs from Hotchkiss) for breakfast and lunch. Find hearty salads, cool soups (gazpacho, watermelon), dips, veggie and bean burgers, enchiladas, and curry bowls, plus cold-pressed juice, tea, and coffee. Plant-rich cuisine defines Pyramid Bistro—without excluding seafood and poultry. Peach’s Corner Café and Jüs (inside the Ute City Bank building) both hawk a variety of meatless salads, sandwiches, and wraps, alongside power juices that are as essential as a yoga mat for Aspen’s fitness-obsessed.

Your credit card is almost maxed out.

Because most of the remaining budget-friendly hangouts are also short on seating (looking at you, Grateful Deli, the Big Wrap, and Ajax Donuts), chances to rub elbows with cash-strapped locals are fading faster than memories of the recently departed Golden Arches on the Mill Street Mall. Still, lunch for less than 15 bucks is achievable elsewhere. Bamboo Bear keeps Aspen funky with authentic—and righteously priced—Southeast Asian fare such as pho and bulgogi, and abundant seating. Other affordable options: 520 Grill, Peach’s Corner Café, Zane’s Tavern, and the Red Onion (plus Justice Snow’s $12 gourmet bar burger is one of the best values around). Happy hour snacks at Hops Culture, Su Casa, and Mi Chola won’t set you back much, either. But beware of blowing your wad on booze; this is the land of the $20 craft cocktail, after all.

You’re (not so) fresh from backpacking to Conundrum hot springs.

Stretch sore legs on the outdoor deck at Home Team BBQ, located inside the Inn at Aspen at the base of Buttermilk. Here in carbo-reload heaven, start by sipping a well-earned, frosty Game Changer (rum, orange and pineapple juices, coconut cream), then dig into spice-rubbed chicken wings, which won the inaugural Great Chicken Wing Throwdown last March. Onto ’cue: St. Louis–style pork ribs, beef brisket, pulled pork, and smoked turkey are served with a choice of seven sides or in sandwiches, tacos, salads, and nachos. Slather them with house-made sauces. Another epic combo: the double-patty burger with an order of chicken-skin cracklins. Up for even more adventure? Dip into Home Team’s tongue-tingling “death relish.”

You’re planning a midday meeting that must impress.

Climb to the top of the Aspen Art Museum (ahem, use the stairs or elevator), where So boasts dead-center views of Aspen Mountain and a tempting menu that changes weekly. Julia and Allen Domingos, of Epicure Catering, switch up the café’s four to five offerings every Tuesday, and rarely do their artistically arranged small plates, salads, soups, and sandwiches repeat. The deal-closer: ample room between tables and noise-muffling latticework surrounding the airy, indoor-outdoor terrace make private conversation entirely possible.

A big salad—and a glass of wine—for lunch sounds just fine.

If alcohol makes the greens go down, consider Pyramid Bistro, the light-filled “nutritarian” dining room on the second floor of Explore Booksellers. An organic quinoa salad with fresh pineapple, avocado, and goji berries meets its match with a glass of Grüner Veltliner. Ajax Tavern boasts a French-accented frisée aux lardons salad with truffle vinaigrette. We can personally attest to its virtues with a glass, or three, of Veuve Clicquot Yellow Label. Cobb salads are having an Aspen moment lately. King of the hill is at the Hotel Jerome’s Prospect restaurant, where the lobster Cobb enjoyed with a bottle of Chablis is one of summer’s great pleasures. Votes also go to the Cobb at The Little Nell's Element 47 (chicken, bacon, avocado, and blue cheese tossed in poblano-ranch dressing). Rumor has it the wine list here is pretty respectable, too.

You’re thirsty for excellent booze (accompanied by a great bite).

Dozens of Aspen restaurants have terrific bars with food that ranges from OK to orgasmic. This summer, though, we’re lavishing extra love on Jimmy’s and Bosq. Jimmy Yeager’s trip to Japan last year resulted in Turning Japanese, a bar-only menu of rare Japanese whiskies and sake cocktails such as Morning Droplets of Dew on Frozen Grapes. Try it, as Yeager suggests, with Thai ahi tuna lettuce wraps with coconut. As for Bosq, chef-owner C. Barclay Dodge’s $20-and-under Bar Bites menu, combined with bartender Alexis Kendall’s equally sophisticated cocktails, is tough to beat. Don’t miss the steamed Peking duck buns or tempura shiitakes, washed down with a barrel-aged Negroni or Boulevardier.

Being served isn’t enough—you’re keen to watch the action up close.

You can fantasize about being a chef with a seat at the sushi bar at Matsuhisa, Kenichi, or Maru. Cooking School of Aspen even lets you try your hand at actually making a dish. But nothing beats the nine comfy counter seats at Chefs Club, overseen by executive chef Todd Slossberg and wine guru Jonathan Pullis. Straight ahead are acres of stainless steel, flaming burners, and cool people cooking your dinner. You’ll overhear the chef de cuisine call out your order, then watch the line cook grill your steak. With luck, you’ll catch a celebrated guest chef carefully plating an entrée with tweezers. (New York’s renowned Missy Robbins once cooked our meal right in front of us, chatting all the while.)

You’d like to laugh with your meal, not at it.

Humor is seldom on the menu in Aspen (or anywhere else, for that matter), so if you want belly laughs while enjoying some very good food, sign up for a cooking class or event with Glenn Smith. One of Aspen’s longtime private chefs, as well as a fishing guide, multimedia artist, and standup comic, Smith leads highly entertaining evenings at Cooking School of Aspen, among other gigs. “My goal has always been to teach people to enjoy cooking, rather than learn to cook,” he says. “Having a sense of humor really helps when you agree to do a seafood class for a corporate group and no one there eats fish. People often take food way too seriously. Food and humor are at their best when they’re both pure and simple.”

All you desire is dinner cooked—and delivered—by someone else.

While most restaurants will pack for takeout nowadays, only a few deliver, and only a couple of those are worth the call. That’s why Tom Engelman launched À La Car in 1996. The “black-tie delivery service” gathers orders from 25 restaurants in Aspen and three in Snowmass, including multiple fine-dining establishments, and shows up within an hour. So go ahead and order artichoke bruschetta from Ellina, lobster from Grey Lady, and Steakhouse No. 316’s bourbon bread pudding, all for one meal. Just expect to pay 20 percent of the total food cost for the convenience.

You’ve already taken the tots to Brunelleschi’s—now what?

DIY pizzas and soft pretzels have delighted finicky young palates at Bruno’s since 2005. (Mix-and-match noodles and the grilled cheese calzone are other safe bets; petite paper chef toques are a bonus.) But if you’re looking to mix it up, head around the corner, where Meat & Cheese Restaurant and Farm Shop balances casual sophistication with kid-friendly creativity. A mother herself, owner Wendy Mitchell has cooked up a compelling menu: chicken and waffles; pork-chicken Sun Noodle ramen; and a gooey cheese quesadilla on local corn tortillas. Rounded out with vegetable crudité and a house-made popsicle (seasonal fruit or chocolate-coconut), these kids’ meals ($9 ) are known to tempt grown-ups, too.

You want to choose dessert first.

Dessert has long been an afterthought in carb-phobic Aspen. An exception is Eight K at the Viceroy Snowmass, where pastry chef Ashley Jenkin has been crafting world-class finishing touches for several years. (Her gluten-free chocolate cake is a local legend.) Then, a few years ago, wonderful dessert crêpes appeared at Alpine bistro La Crêperie du Village. Now another classic French dessert is in the spotlight: vacherin. Try it at Chefs Club, where new pastry wizard Amanda Sinclair composes an almost-too-pretty-to-eat version of the meringue and whipped cream extravaganza, recently rich with coconut, mango, and passion fruit. Carolina Polo, newly installed at the St. Regis Aspen’s restaurant, the Portal @ TQD, offers vacherin glacé, with ice cream between the meringue layers.

You have an appetite for a side of live music.

No, we’re not talking about folksingers warbling John Denver while you down a bucket o’ wings. At Belly Up, the food may not equal the music, but items such as the salmon patty wrap and pulled pork flatbread are better than you might expect. For gourmet grub, try the grilled New York strip or lamb shank at musically inclined Justice Snow’s or nosh on a variety of wood-fired pizzas at the Lounge in the Limelight Hotel—both packed with locals. Unbeatable, though, is the Jazz Aspen Snowmass JAS Café, which features supercharged jazz performances in various venues. If you’re lucky, tickets are still available at Cooking School of Aspen for Hammond B3 organ master Dr. Lonnie Smith (July 7–8 ) or the program dubbed Ella & Louis Together Again (July 29–30 ). Tickets for the early shows include a three-course dinner from Rustique Bistro, upstairs from the school, while the later show offers an à la carte menu.

You’re in charge of reservations for a group of picky eaters.

Pleasing your whole posse can be tough, even in Aspen. Our can’t-miss pick: White House Tavern, where the limited menu of spot-on dishes makes it easy for both the indecisive and the fussiest fault-finder. Everything here is so much better than it has to be, from house-made sandwich buns to carefully composed salads to solicitous service. There’s a crispy chicken sandwich on nearly every table, and for good reason. The Thai steak and noodle salad is bright with mango and mint. The tabbouleh is a long way from the usual oily mess. Even Mr. Grumpy would be tickled here.

You yearn to noodle-brag on social media.

Painstakingly made fresh pasta is easy to find around town—from creamy garganelli carbonara and seafood-topped squid-ink spaghetti at L’Hostaria to lemon fettucine with peas and virtuous spinach gnocchi at Campo de Fiori. Acquolina stuffs tortelloni with asparagus and ham. Cache Cache, a perennial crowd favorite at the annual Aspen Mac and Cheese Festival, offers supple pasta specials nightly (and chef Nate King is freshly inspired from a recent Italy trip). Japanese Maru pulls its ramen strands from scratch. And don’t overlook the Wild Fig, where veteran chef Pompey Lopez fuses Mediterranean, French, and Italian flavors into saffron spaghettini with Manila clams.

A real meal is necessary, and it’s after midnight.

While slices at New York Pizza might taste like masterpieces under certain circumstances, options are scarce for those seeking a swankier setting in the wee hours. By scarce, we mean two. Rickhouse Social, the nightclub and whiskey bar beneath Aspen Kitchen, serves executive chef Matthew O’Neill’s craveable bar menu from the restaurant upstairs until 12:30 a.m. Try tater tots with caviar and house-made crème fraîche, “clothesline bacon,” or a massive 30-day-aged burger on beef-fat brioche. Three blocks west, Hooch slings speakeasy snacks inspired by upstairs restaurant Meat and Cheese until 1 a.m.: charcuterie boards and heartier plates with Asian flair, including pork bánh mì and spicy dan dan noodles.

You need privacy in public.

We get the appeal of curtained-off “rock-star booths” at Kenichi. And at Plato’s at the Aspen Meadows Resort, all eyes will be glued on the tempting food, classic mid-century décor, or dramatic sunset. So why are we sending you and your lover/anonymous source/co-conspirator over to the Artisan at the Stonebridge Inn, halfway up the steep road to the Snowmass Mall? Because this restaurant deserves exposure, even if you don’t want any. Executive chef Steven Sterritt excels at contemporary mountain fare like Colorado striped bass with citrus beurre blanc and jumbo pork porterhouse with bourbon-peppercorn cream. On a warm night, request a table on the terrace. Then start with the duck toast, laden with duck confit and a 63-degree egg, or the grilled artichoke. This being Snowmass, you’re not likely to be recognized by your wife’s lawyer or your hedge-fund partners. 

You’re hungry for a change of scenery.

Aspen may get all the glory, but Basalt sits closer to farmland—and that’s where a hot new restaurant is changing the conversation about local food. Free Range Kitchen and Wine Bar is led by industry stalwarts and oenophiles Steve and Robin Humble (formerly of Renaissance and the Roaring Fork Club), along with executive chef Flip Wise and sous chef Patrick Kennedy (erstwhile head butcher at Meat and Cheese and original salumiere at Avalanche Cheese Company, respectively). The team fires up one of the area’s few wood-burning ovens, turning out smoky, savory dishes that give star billing to ultra-fresh fare. No surprise, then, that the rustic-chic joint is always packed; reservations are a good idea.