On summer weekends, parked cars line Montauk Highway on either side of this Caribbean-style seafood shack. By day, families and older couples dine under umbrellas at tables set with disposable flatware on a gravel-floored courtyard. Menu favorites include spicy, lightly fried squid in a Buffalo-style sauce tempered with blue-cheese dressing and a tasty sandwich of flounder dredged in a garlic-and-pepper batter. As night falls, the roadside shack transforms into a packed pickup joint for tank-top- and flip-flop-clad singles downing rum punch and frozen margaritas. Cyril, with his white beard, funky sunglasses, straw hat, and (if you're lucky) flowing sarong, works the crowd. The bohemian proprietor is quick to accept a drink, but he doesn't accept credit cards—so bring cash or you'll be saddled with his high ATM fee.

Open daily 11 am to 10 pm, mid-April through early October.

From the rosemary-and-juniper-marinated pork tenderloin with honeyed root vegetables to the flourless Valrhona chocolate soufflé topped with dark cherry gelato, candied pistachios, and classic caramel, it's hard to find an unappetizing bite on chef Michael Rozzi's menu, which stars local, organic ingredients. Knowledgeable servers crouch beside tables, animatedly describing specials. Diners waiting for seats linger at the handsome bar, sipping cocktails like the Italian Dreams, a refreshingly bittersweet mix of Campari, orange juice, limoncello, and vodka. The crowd ranges from the posh and powerful old guard to trendy young summer babes. And on the walls, countless caricatures of famous patrons attest to Della Femina's popularity with vacationing celebs.

Open Mondays through Saturdays 6 to 9:30 pm, Sundays noon to 2:30 pm and 6 to 9:30 pm.

The East End is loaded with gourmet grocery stores peddling the stuff of fabulous dinner parties ($100/pound lobster salad, anyone?) But there's also great local produce at the area's farm stands, which make good bicycling pit stops as well as prime prospects for surreptitious celebrity sightings. The Halsey family sells apples, peaches, and cider donuts from the Milk Pail Country Store on Montauk Highway near Bridgehampton and, from September through October, at their nearby U-Pick Apple and Pumpkin Farm (631-537-2565; www.milk-pail.com). Fairview Farm on Horsemill Lane in Bridgehampton has cheese from local Mecox Bay Dairy, fresh iced ginger tea, and other local treats—and runs a cornfield maze each year between September and November (631-537-6154; www.fairviewfarmatmecox.com). The Pike Farms stands on bucolic Sagg Main Street in Sagaponack and is known for its tomatoes and corn, which are sweetest during late summer.

In 2006 (after 25 years in business), this perennial favorite moved from a location near the East Hampton train station to a renovated farmhouse with a screened-in patio on the road to Amagansett. The digs may be old, but the renovation—brown leather banquettes and a black marble bar—is thoroughly modern. Executive chef Andrew Engle, formerly chef de cuisine at Manhattan's Oceana, is a longtime believer in the environmental and culinary advantages of sustainable cuisine, and he carefully selects local ingredients to include in his fresh, flavorful New American menu. Sweet peas from Satur Farms in Cutchogue and ricotta cheese are tucked into ravioli, freshly shucked Pipes Cove oysters are served on the half shell, and chicken from East Hampton's Iacono Farm comes with garlicky mashed potatoes and seasonal vegetables. Legions of fans wouldn't have it any other way.

Open daily 5:30 to 11 pm.

After 40 years, the Lobster Roll remains the quintessential Long Island seafood joint. Also known as Lunch, thanks to the sign on top of the roof, this seasonal spot welcomes families with a kid-friendly menu, a warm staff, fast service, and a casual dining space. Groups gather on bench seats for bowls of mellow lobster bisque; tender, well-spiced crab cakes; old-fashioned egg creams; and, of course, the famous lobster roll—a classic that comes on an overstuffed hot-dog bun, with creamy mayo and crunchy celery. (Open April through November; weekends only before Memorial Day and after Labor Day. Their other location is at 3225 Sound Ave., Baiting Hollow, Riverhead; 631-369-3039.) Less flashy and storied, the Clam Bar, in a diminutive red roadside shack a stone's throw down Montauk Highway, serves up quality fried clams, burgers, and, to some minds, a superior lobster roll. Eating this close to the road is like driving in a convertible—the wind blows your hair, and it feels like summer. Plus there is something comforting about the nonambience and limited charms of picnic tables shaded by umbrellas and the posted warning signs about letting children wander freely (2025 Montauk Hwy., Amagansett; 631-267-6348).

You'll find Mirko's behind an enclave of shops and through a small parking lot packed with Ferraris and Jaguars—a sign of its fabulously rich, sometimes famous, and intensely devoted clientele. A sunny French-country dining room is complemented in summer by a private patio and in winter by a crackling fireplace. In the kitchen, chef Mirko Zagar works his magic: An artfully presented vegetable risotto is dotted with crisp slices of asparagus and snap peas. A grilled shrimp curls around a chive flower and a sprig of oregano. On the otherwise descriptive dessert menu, one item is listed simply as "The Pear." This house specialty is poached, dipped in rich dark chocolate, and served whole over vanilla ice cream, and is delicious beyond words.

Open Tuesdays through Sundays 5:30 to 10 pm.

Here's a taste of Hamptons hospitality, accompanied by a heaping side of boldface names: A gracious hostess guides you past tables commandeered by the likes of Martha Stewart, Jerry Seinfeld, and Ron Perelman, and a knowledgeable waitress delivers a comforting plate of free-range chicken with roasted vegetables and garlic jus. Granted, if you're not an A-lister, a Friday or Saturday night reservation can be impossible (call one month ahead, starting at 9 am, and be prepared to redial). But if you score a seat, you'll be well taken care of, no matter who you are. During the summer, outdoor tables provide much-needed extra seating, and a pleasantly private back room is less hectic (though also excluded from the celeb spotting). On slower nights—Wednesday, Thursday, and Sunday—wood-oven pizzas please the regulars.

Open nightly from 6 pm.

For a relaxed dinner at a French bistro, head to the Red/Bar Brasserie early on a weeknight—in the off-season. Between June and September, Red/Bar's high-wattage clientele (shock jock Howard Stern and fiancée Beth Ostrosky are regulars), park their Land Rovers up and down Hampton Road and pack into the dining room. They come for Chef Erik Nodeland's top-flight bistro fare, such as garlicky steamed Prince Edward mussels in a white wine broth, and tender, truffle-scented chicken breast paired with a hearty wild mushroom risotto. Try for one of the banquettes in the center of the dining room to best take it all in. There's also a happening scene at the tiny bar, where the crowd downs potent martinis and glasses of white wine from the nearby Channing Daughters vineyard and grooves to a Brazilian beat.

Open nightly from 6 pm.

Southampton is the most self-consciously dressed up of the Hamptons, so it makes sense that Main Street would be the spot for an outpost of this Manhattan gelateria and restaurant. This is the place to go when you've had enough of the sun-soaked beach atmosphere and feel the need to stand at a bar and be served a $6 cappuccino and an equally overpriced prosciutto-and-fresh-mozzarella focaccia sandwich by wisecracking Italian-speaking gentlemen in black ties and vests. Up front is a long glass case with many flavors of gelato (try the mango or blueberry); in the back is a small, more formal dining room that serves Italian standards such as spaghetti alla bolognese, risotto with asparagus, and breaded veal chops.

Open daily 10 am to 10 pm.

If minimalist architect Richard Meier designed a BBQ joint, then Townline BBQ might be the outcome. A boar's head over the fireplace and a pool table are the only embellishments to the reclaimed wood–clad walls and long wood tables. Step up to the counter and order pulled pork sandwiches piled high with coleslaw, pickles, and jalape1os, substantial racks of beef or pork ribs, fried mac 'n' cheese, and rich icebox cake. And watch for Kelly Ripa, Mark Consuelos, and their kids tucking into pork ribs, French fries, and Texas chili. Wash the tangy Texas-style, house-smoked barbecue down with a spicy Bloody Mary (crafted with Tito's Handmade Vodka from Austin, Texas) or a Blue Point Toasted Lager. If you want margaritas with your ribs, opt instead for Tex-Mex Turtle Crossing in East Hampton.

Open Sundays through Thursdays 11:30 am to 10 pm, Fridays and Saturdays 11:30 am to 11 pm.

This Southwestern barbecue joint, adorned with cowboy kitsch, is one of East Hampton's most pleasant surprises. House-smoked meats are better than they're expected to be this far north of the Mason-Dixon Line, and the margaritas are fresh and massive. Try the charred pulled-chicken sandwich, served on a brioche with sweet, smoky barbecue sauce and crisp pickles; or the mouthwatering signature quesadilla, filled with caramelized onions, guacamole, fresh mango salsa, and Jack cheese. Famous patrons include the Clintons and the Spielbergs, but the affable staff doesn't put on airs. Takeout is available, too, and a large refrigerated case houses six-packs of well-matched beers, including Dos Equis and Negro Modelo.

Open Mondays through Thursdays 5 to 10 pm, Fridays 5 to 11 pm, Saturdays and Sundays noon to 10 pm, May through November.

On summer evenings, this Shelter Island favorite, housed in a newly renovated, white-shingled ranch with flower-filled window boxes, quickly fills up with a beach-chic crowd that spills out to the picnic tables. Celebs such as actor John Malkovich, designer Jonathan Adler, and style maven Simon Doonan often stop by for the fresh fare: tuna tataki pepped up with wasabi; heirloom tomatoes with basil, Parmesan, and Vidalia onions; and perfectly prepared filet mignon. Be sure to save room for a side dish—the crisp frites with garlic aioli are sublime.

Open Sundays, Mondays, and Thursdays 5 to 9:30 pm, Fridays and Saturdays 5 to 10 pm.