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.
8:30 p.m.
3. WAY OFF BROADWAY
New Haven's a theater town, with three well-respected playhouses, each with its own creative niche. Near the industrial waterfront at the foot of the city's food terminal, Long Wharf Theater (222 Sargent Drive; 203-787-4282; longwharf.org), founded in 1965, has drawn Hollywood powerhouses like Al Pacino and Kevin Spacey, as well as up-and-coming Broadway talent. This season, guests will watch Kathleen Turner's take on "The Killing of Sister George" from new, cushier seats, following the theater's first major renovation, which also brings a new bar and expanded lobby.
11 p.m.
4. PORTER AND PUNK
On a two-block stretch best known for thumping multistory clubs, the Cask Republic (179 Crown Street; 475-238-8335; thecaskrepublic.com) is a comparably more studious place devoted to the less-than-quiet contemplation of fine ales, lagers, stouts and porters — some 60 or so on draft alone, including rare and cask-conditioned beers. For live jazz or punk rock, Scottish folk or Texas blues, settle in at the newly remodeled Cafe Nine (250 State Street; 203-789-8281; cafenine.com), beloved by locals and dubbed the "musician's living room" for its intimate scale. Along Crown Street, notice the Walk of Fame-style stars embedded in the sidewalk, the work of the artist Sheila Levrant de Bretteville, designed to celebrate New Haven's grocers, cigar strippers and ship captains of New Haven's past.
Saturday
9 a.m.
5. EAT, THEN LEAF-PEEP
In the quiet Westville neighborhood, Bella's Café (896 Whalley Avenue; 203-387-7107; bellascafect.com) has an eclectic brunch menu that ranges from Oscar Benedict (poached eggs, petit tenderloin, asparagus and crab meat, with potatoes and béarnaise sauce; $16.95) to pecan-crusted catfish in a Creole sauce, with poached eggs and Cheddar cheese-roasted poblano grits ($14.95). For leaf-peeping, walk the banks of the West River in the 120-acre Frederick Law Olmsted Jr.-designed Edgewood Park (Edgewood Avenue).
12 p.m.
6. ART FOR FREE
After a 14-year renovation, the Yale University Art Gallery (1111 Chapel Street; 203-432-0600; artgallery.yale.edu) will reopen in December. The expansion means greater access (and free) to the gallery's 200,000-piece collection. Across the street, the equally impressive (also free) Yale Center for British Art (1080 Chapel Street; 203-432-2800; ycba.yale.edu) holds the largest collection of British art outside Britain, from the dramatic George Stubbs lion-and-horse oil paintings to Francis Bacon's Surrealist triptychs to the Pop Art of the 1960s.
1 p.m.
7. SAY CHEESE
Its crowded shelves of imported artisanal pasta and olive oils are reason enough to make the trek to Liuzzi Gourmet Gourmet Market (322 State Street, North Haven; 203-248-4356; liuzzicheese.com). But the shop also sells sandwiches made with cured meats, like Parma prosciutto and sopressata, and house-made cheeses, like ricotta salata and burrata. Or try Caseus Fromagerie Bistro (93 Whitney Avenue; 203-624-3373; caseusnewhaven.com), where patio tables are warmed by heat lamps, perfect for savoring comfort food — poutine (pommes frites, cheese curds, velouté; $9) or the PFT sandwich (prosciutto, fig jam, Taleggio cheese; $14).
3 p.m.
8. STYLE AND SUBSTANCE
Next door, Fashionista Vintage & Variety (93 Whitney Avenue; 203-777-4434; fashionista-vintage-variety.com) sells hand-selected costumes (harem outfits, animal heads) and vintage wear, including men's clothing and dresses that Betty Draper would covet. At 116 Crown (116 Crown Street; 203-777-3116; 116crown.com), learn the art of boutique and esoteric ingredients at a cocktail class taught by John Ginnetti, one of Connecticut's most revered bartenders. Each class (from $45 a person; about two hours) includes five half-drinks per student. Reserve one to two weeks in advance.
5 p.m.
9. THE OUTLOOK'S FINE
Drive to the top of the 426-acre East Rock Park, where a 350-foot basalt cliff offers a magnificent vantage for catching the sunset over Elm City and Long Island Sound, just before the park closes. (Information: cityofnewhaven.com/Parks.)
8 p.m.
10. OLD-WORLD NEW ENGLAND
A French restaurant in the high Yankee style, Union League Cafe (1032 Chapel Street; 203-562-4299; unionleaguecafe.com) has an inscription above the fireplace marking a 1789 visit by George Washington. This mix of history and Beaux-Arts grandeur is half the reason for visiting; the other half is service that's formal without being finicky, and food (entrees $21 to $34) that tastes decadent — foie gras, caviar and truffles — without being overly rich.
10 p.m.
11. RETRO BAR CRAWL
If only for the atmosphere, stop by the Owl Shop (268 College Street; 203-624-3250; owlshopcigars.com), a vintage cigar lounge draped in leather and wood, where bourbon flows and tobacco is blended. Next door, Anchor Restaurant (272 College Street; 203-865-1512) has lighthouse-shaped lamps, blue vinyl booths and a neon-lit Rock-Ola jukebox. Recently uprooted from its longtime home, Rudy's (1227 Chapel Street; 203-865-1242; rudysnewhaven.com) is no longer the charmingly grimy dive bar it was, but the back room still pays homage to Yale football, and the frites ($5 to $11) are still hand-cut, twice-cooked and Samurai sauce-ready.
Sunday
9 a.m.
12. PARK BENCH BREAKFAST
In the shadow of the Corinthian portico and steeple of St. Michael's Catholic Church, designed in 1855 and among Connecticut's first Italian-American churches, Wooster Square is awash in church bells and bordered by cherry trees. Stop at Lucibello's Italian Pastry Shop (935 Grand Avenue; 203-562-4083; lucibellospastry.com) for marzipan-flavored, pine nut-topped pignoli, clam-shaped sfogliatelle and crispy cannolis, and the at the friendly coffee shop Fuel (516 Chapel Street; 203-773-5005), down the street, for an espresso to go.
Noon
13. KEEP ROLLIN'
You can pass the rest of the morning wandering the Yale campus at its most peaceful, when the architecture (yale.edu/architectureofyale), from the 1752 Connecticut Hall to the turtle-shaped shell of the 1958 Eero Saarinen ice skating rink, takes center stage. Then, window-shop your way up boutique- and bookstore-lined Chapel Street to Miya's Sushi (68 Howe Street; 203-777-9760; miyassushi.com), where the menu is part manifesto on sustainability, part multicultural poetry. Rolls include Charlie Chan's Ching Chong Roll (whole wheat tempura broccoli, garlic and black beans; $6) and the Japafrican Queen (eggplant, goat cheese, apricots, avocado, pickled radish, chives and berbere spice mix, rolled in Ethiopian injera bread; $8).
IF YOU GO
The 124-room Study at Yale (1157 Chapel Street; 203-503-3900; studyhotels.com) plays on its university connection with a lobby of bookshelves, leather armchairs and modern art. From $289.
On the upper floors of one of downtown's taller buildings, many of the rooms at the recently renovated Omni New Haven Hotel at Yale (155 Temple Street; 203-772-6664; omnihotels.com) offer views of the Yale campus or Long Island Sound. From $251.
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