Downtown and the Strip District
Although, Downtown (a.k.a. "The Golden Triangle") contains only a hint of what greater Pittsburgh has to offer, its handsome contemporary skyline and regal command over the confluence of the Ohio, Allegheny, and Monongahela rivers imbues it with a stately countenance. Begin exploring at landscaped Point State Park, where Forts Duquesne (pronounced doo-kane) and Pitt once guarded the settlement. Today, the Fort Pitt Museum houses exhibits on the city's early history.
The Golden Triangle comprises Pittsburgh's thriving business district, but aside from the eclectic architecture and the live bands entertaining lunchtime brown baggers at Market Square (at Forbes Ave. and Market St.), there are few major attractions here. The square, however, lies in the shadows of Pittsburgh's most remarked-upon building, PPG Place (at Stanwix St. and 4th Ave.), a neo-Gothic monolith designed by openly gay architectural icon Philip Johnson. Liberty Avenue runs northeast from near here and has several of the city's most popular gay bars; with parallel Penn Avenue they're the spines of a 14-block Cultural District (a.k.a. "The Penn/Liberty District") of theaters and performance halls housing the Pittsburgh Symphony Orchestra, the Pittsburgh Ballet, the Pittsburgh Opera, and other well-regarded theater companies.
Penn Avenue leads northeast to a historic warehouse district, The Strip, that's now a clutch of nightclubs, hip restaurants, art galleries, and offbeat shops; many businesses here have an artsy and fairly gay following. Adjacent is Down by the Riverside Boardwalk, a massive complex with a marina, restaurants, and a floating boardwalk, and the John Heinz Pittsburgh Regional History Center, a fantastic museum that chronicles the city's history with imaginative exhibits and memorabilia.
The North Side lies just across the Allegheny River from downtown and is home to PNC Park, home of the baseball's Pirates; Heinz Field, home of football's Steelers; and a slew of intriguing arts and cultural attractions. The Andy Warhol Museum celebrates the life of the late Pop Art icon, who grew up in nearby Oakland. Created inside an eight-story 1911 steel supply warehouse, the museum contains 8,000 works and is an outstanding, engaging, and often very funny museum, laid out with abundant commentary on Warhol's life (and his homosexuality).
Within walking distance are the kid-friendly Carnegie Science Center; the http://www.aviary.org/National Aviary, with its numerous bird-life habitats that allow up-close looks at species from around the world; and the Mattress Factory Art Museum, known for its provocative larger-than-life installations created by visiting artists in residence. The Mattress Factory is also home to a great little eatery and coffeehouse, the Box Spring Cafe. It's located in the historic Mexican War Streets neighborhood, a 27-acre area whose narrow streets are lined with beautifully restored town houses, mostly from the 1840s and '50s. You'll detect a handful of rainbow flags in this diverse district.
South Side and Mt. Washington
South of downtown, across the Monongahela, the city rises sharply above the river toward Mt. Washington, a workaday neighborhood whose commercial drag, Grandview Avenue, hugs the ridgeline and offers spectacular views downtown. Ride up the slope via the Monongahela Incline, by Station Square, which leads to a viewing platform and a small museum. You can combine your ride on the incline with a visit to Station Square, a redbrick complex, formerly a freight yard, that houses quirky stores, a Sheraton Hotel, and some touristy nightclubs and restaurants.
A short drive east is the bohemian South Side, a repository of funky shops, galleries, and eateries. Once the heart of the city's Lithuanian and Polish communities, Carson Street is now lined with music stores, bric-a-brac emporia, coffeehouses, and edgy galleries.
Lawrenceville and Polish Hill
Follow Penn Avenue northeast from the Strip District, turning left and continuing onto Butler Street, and for nearly 2 miles along Butler you'll pass through the heart of one of the most interesting, creative, and eclectic neighborhoods in the city, Lawrenceville. This largely working-class district whose blocks were laid out in the early 19th century by the father of composer Stephen Foster have in recent years attracted artists, students, designers, gays and lesbians, young families, and hipsters - you'll find some of the hottest restaurants and distinct shops and galleries in these parts, plus a couple of gay bars.
Oakland, Shadyside, Squirrel Hill, and East Liberty
A few miles east of downtown, Oakland was built from the gobs of money generated during Pittsburgh's industrial heyday and today contains offices, hospitals, universities, businesses, and the heart of the city's computer software industry. Forbes and 5th avenues anchor the University of Pittsburgh and formidably endowed Carnegie Mellon University. Collegiate shops and cafés surround these two campuses, both of which have their share of attractions. At CMU, visit the four Carnegie Museums of Art and Natural History, which contain well-conceived architectural and decorative arts exhibits, a cache of artifacts from ancient Egypt, and the nation's third-largest dinosaur collection.
Across the street, towering 42-stories above Pitt's campus, is the second-tallest school building in the Western world, the Gothic-style Cathedral of Learning. Head to the 36th-floor observation deck for views of the region. Nearby Schenley Park, ideal for a stroll, is anchored by the 1893 Phipps Conservatory, comprising 13 rooms of exotic flora.
East of Oakland is Shadyside, a gentrified patch of neatly kept yards and attractive old homes. Although more queers live here than elsewhere in Pittsburgh, it's a mixed neighborhood and by no means strictly or even predominantly a gay neighborhood. Ellsworth Avenue (around the 5800 block) has several gay-popular eateries and businesses, and more chichi Walnut Street (along the 5500 block) holds mid- to high-end chain stores. As you venture a bit east on Ellsworth Avenue to Penn Avenue, a left turn leads into another up-and-coming neighborhood of hip restaurants, mixed gay-straight lounges, and indie shopping, East Liberty.
Just south of Shadyside, Squirrel Hill is a charming neighborhood of known for its ethnic restaurants and small-town vibe - quite a few students and faculty from nearby Carnegie Mellon and Pitt live here.
It's a short drive east to Clayton, the Frick Art and Historical Center, the former estate of industrialist Henry Clay Frick that now consists of a magnificent mansion and other historic outbuildings. The center contains an outstanding collection of European master paintings.
Side Trip to Fallingwater
Frank Lloyd Wright's most celebrated residential creation, Fallingwater is worth the 90-minute drive. To reach the house, which is cantilevered precipitously above a rushing waterfall, head southeast about 60 miles on the Pennsylvania Turnpike to Donegal; from here drive 15 miles south on Route 381. You can also by a combination ticket good for admission and a tour of Kentuck Knob, one of Wright's later residential creations, which is just a 15-mile (windy, though scenic) drive from Fallingwater. It's an interesting house, more intimate than Fallingwater, and well worth touring as well.