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Rambling Rose: Strolling Into Fall

Like food itself, the act of eating is seasonal. When it’s warm out, we yearn to dine alfresco; once it’s winter, eating becomes an indoor sport (often involving the consumption of Oreos, on the couch, in sweatpants).

So while autumn is upon us, it’s important to revel in the crispness of the air and partake of some freshly prepared meals. We suggest trying one of these progressive-dinner itineraries. These neighborhood-centric, pedestrian-friendly, cocktail-dinner-dessert tours offer the perfect intermezzos to an evening of eating entertainment—a little fall-weather stroll.

Central West End

Predinner Cocktail: Maryland House at Brennan’s
The cocktails at this hidden upstairs haunt (accessible by an unmarked door adjacent to Brennan’s entrance) are fishbowl-big and the result of some wild mixology. Should you arrive and it’s not open, ask the staff at Brennan’s for a bubbly recommendation, and enjoy it in the cellar lounge or at a sidewalk table.

Dinner: Bar Italia
Who needs the Mediterranean when you’ve got the wide-open patio at Bar Italia? Pretend the sound of cars whooshing past is really waves cresting ashore, and order up a fresh-weather feast to graze upon: bruschetta, Caprese salad, torta rustica, and pollo alla griglia.

Dessert: Bissinger’s at Maryland Plaza
Wrap up your night with a single biscotto—the best you’ve ever had—because, unlike other biscotti, this one was made today. But who are we kidding? There’s no way to be demure about desserts amid all of Bissinger’s delectable chocolates.

Lafayette Square

Predinner Cocktail: 33 Wine Shop & Tasting Bar
OK, so champagne isn’t exactly a cocktail. But let these guys steer you toward a lovely, dry split of bubbles and begin your evening with a touch of aristocratic revelry.

Dinner: Eleven Eleven Mississippi
If you’re going to pretend it’s still summer, you might as well pretend you’re in Napa County while you’re at it. Head west via the wild-boar ravioli, slow-braised rabbit, or Alaskan halibut.

Dessert: Baileys’ Chocolate Bar
Its name tells you exactly what it is. We suggest dining outside, where candles often outnumber people.

The Loop

Predinner Cocktail: The Delmar Restaurant & Lounge
The secret nobody knows about The Delmar is, the earlier you show up, the more sophisticated its Rat Pack–throwback environs. Order a martini, or anything else served in a martini glass, like a Gibson or Manhattan.

Dinner: Riddles Penultimate Café & Wine Bar
If The Delmar suggests the Mad Men vibe of the ’60s, Riddles would be the groove of the Grateful Dead. Whatever’s on the seasonal menu that night, it’s almost guaranteed not to show up again for months, so dig in.

Dessert: FroYo
A cavalcade of toppings and nonfat frozen yogurt constitute a one-two punch to the taste buds. Load up your pay-by-the-ounce cup with blackberries, strawberries, and watermelon; save the chocolate-chip cookie dough and cheesecake bites for those debaucherous nights when FroYo is dinner.

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