Best History Lesson: Most Pittsburghers agree that the Senator John Heinz Pittsburgh Regional History Center (1212 Smallman St., 412/454-6000, www.pghhistory.org , daily 10 a.m.–5 p.m., $7.50 adult, $5 student, $3.50 child (ages 6–18), free for children ages 5 and under, $6 senior) has done a fantastic job of documenting and presenting the history, culture, and attendant struggles of the Southwestern Pennsylvania region. And while much of the museum is serious business, there’s more than enough here to keep kids amused.
Best Gothic Landmark: Certainly one of Pittsburgh’s most beloved structures, the Cathedral of Learning (Corner of 5th Ave. and Bigelow Blvd., 412/624-4141, www.pitt.edu , free), which happens to be the second-tallest educational building in the world, can be spotted from hundreds of different vantage points throughout the city.
Best Park: If you haven’t been to Schenley Park (Schenley Park Visitors Center, Panther Hollow Rd., 412/687-1800, www.pittsburghparks.org , daily 10 a.m.–4 p.m.), you haven’t witnessed the full diversity of the student-filled district of Oakland. Free films are screened on the park’s Flagstaff Hill throughout the summer, paths for walking and jogging are plentiful, and the café next to Phipps Conservatory is probably the most peaceful in the entire East End.
Best Way to Enjoy the Three Rivers: The many vessels of the Gateway Clipper Fleet (412/355-7980, www.gatewayclipper.com , cruise prices vary) ferry tourists and locals alike throughout the farthest stretches of the Allegheny, Ohio, and Monongahela Rivers — even during the depths of winter.
Best Skyline Views: A historic hillside neighborhood packed tight with rickety row houses, the South Side Slopes (www.southsideslopes.org ) was built for the Eastern European immigrants who toiled in the riverside mills below. Not only does a stroll through the area provide a great workout, it also offers some of the city’s most incredible skyline views.
Best Mountainside Ride: Pitts-burgh’s cable-powered Duquesne (1220 Grandview Ave., 412/381-1665, www.incline.cc ) and Monongahela Inclines (Smithfield Street Bridge, 412/442-2000, www.stationsquare.com/info/inclines.cfm ) shuttle passengers back and forth between Mount Washington and the South Side. Tickets run $1.75, or $2.25 with a transfer. Definitely not a journey for the faint of heart.
Best Museum: Controversial, shocking, and endlessly entertaining, the North Side’s Andy Warhol Museum (117 Sandusky St., 412/237-8300, www.warhol.org , Tue.–Thurs. and Sat.–Sun. 10 a.m.–5 p.m., Fri. 10 a.m.–10 p.m., closed Mon., $10 adult, $6 child, $7 senior) is the largest official space dedicated to a single artist in the United States. The novelty-packed gift shop is practically a pop art museum in its own right.
Best Church: With its jaw-dropping collection of stained-glass windows and frightfully lifelike gargoyle busts, the North Side’s Calvary United Methodist Church (971 Beech Ave., 412/231-2007, www.calvarymethodistpittsburgh.org , group tours given by appointment only, free) is a near-masterpiece of late 19th-century Gothic architecture.
Best Body and Mind Workout: A parking lot on the North Shore separates kid-friendly but intellectual Carnegie Science Center and UPMC SportsWorks (1 Allegheny Ave., 412/237-3400, www.carnegiescience.org , Sun.–Fri. 10 a.m.–5 p.m., Sat. 10 a.m.–7 p.m., $14 adult, $10 child and senior), an entirely interactive museum where young and old alike can learn how the body works by working out themselves.
Most Historic Amusement Park: One of the oldest operating amusement parks in the United States — and now a designated National Historic Landmark — Kennywood Amusement Park (4800 Kennywood Blvd., West Mifflin, 412/461-0500, www.kennywood.com , Memorial Day–Labor Day daily 10:30 a.m.–10 p.m., $28.95 adult, $18 child under 46 inches, $14.95 senior) features acres of thrill rides, an unmatched collection of wooden and steel coasters, and oodles of deep-fried junk food.