IT wasn’t long ago that New Haven was the poster child for the troubled college town, a place where the graduates of prep schools rubbed shoulders with the trauma of the mid-’80s and early-’90s crack epidemic. While New Haven’s hard luck reputation lingers, it’s no longer fully deserved. The city’s historic center, which fans out around twin lawns planted with towering elms, maintains an old New England character, with neo-Gothic towers, well-aged dive bars and working-class neighborhoods of faded but elegant Victorian houses. While town and gown have worked to attract brand-name businesses to downtown (among them a new Apple Store and Shake Shack), New Haven remains complex and layered — a city of taco trucks and barbecue shacks as well as high-end clothiers and stylish cocktail lounges.

Friday

5 p.m.

1. GET COASTAL

Take a walk along Long Island Sound, from Sandy Point Bird Sanctuary (Beach Street, West Haven), where birders gawk at red-billed oystercatchers and green-winged monk parakeets, to Bradley Point Beach (Captain Thomas Boulevard, West Haven), near the site of the British invasion of July 5, 1779. Between the two, a paved 1.7-mile promenade keeps the sand from your toes. At sunset, stop into the scuba-themed Dive Bar & Restaurant (24 Ocean Avenue, West Haven; 203-933-3483; divebarandrestaurant.com) for an $8 cocktail — a margarita, Key lime martini or a spicy mojito — or a flight ($12 to $14) of five pours from the rotating tap of 10 craft beers.

7 p.m.

2. APIZZA APLENTY

In the perennial debate over which local joint serves the superior New Haven-style pie, Zuppardi’s Apizza (179 Union Avenue, West Haven; 203-934-1949; zuppardisapizza.com), nearly 80 years old, is too often overlooked. On an otherwise residential street, behind a red, green and white awning, Zuppardi’s has wood-paneled walls and families crammed into orange vinyl booths eating Napolitano “apizza” (pronounced “ah-BEETZ”). Order the fresh clam ($22.75 to $38.25), a thin, bubbling, slightly blackened crust, brushed with olive oil, garlic and parsley and loaded with just-shucked little neck clams.