The Two-Day Best of Pittsburgh

Although a thorough exploration of Pittsburgh and its environs would require at least a week, the city is compact enough that its most important sights and activities can be experienced easily in two days. The following itinerary assumes a Saturday-morning arrival in Pittsburgh, but with the exception of a visit to the Strip District, which is at its best on Saturday mornings, all the activities below can easily be shuffled around at will.

Thankfully, getting around Pittsburgh is also a snap. The Downtown district is walkable, and a fleet of public buses originating in the Golden Triangle serves nearly every obscure outpost in town.

Day 1

Start your visit with an early-morning trip to the Strip District. Stop by Pamela’s Diner (60 21st St., 412/281-6366, www.pamelasdiner.com [1]) for breakfast and then join the throngs of shoppers searching for kitschy souvenirs along Penn Avenue [2]. Afterward, spend an hour or two at the Senator John Heinz Pittsburgh Regional History Center (1212 Smallman St., 412/454-6000, www.pghhistory.org [3]).

Should you find yourself in the mood for fine dining, head to the historic Grand Concourse (100 W. Station Square Dr., 412/261-1717, www.muer.com [4]), but be sure to bring the AmEx along! Afterward, make your way down East Carson Street toward the South Side Flats for a bit of late-afternoon shopping.

Eco warriors will be thrilled with the selection of natural gifts at E House (1511 E. Carson St., 412/488-7455, www.ehousecompany.com [5]), while women on the prowl for quality denim would be wise to check out the selection at Pittsburgh Jeans Company (2222 E. Carson St., 412/381-5326, www.pittsburghjeanscompany.com [6]). Globetrotters will appreciate the quirky Asian imports at the Culture Shop (1602 E. Carson St., 412/481-8284).

For more mainstream window shopping, continue on to SouthSide Works (445 S. 27th St., 412/481-8800, www.southsideworks.com [7]) at the far end of East Carson Street, where popular chain stores like REI, Benetton, and Urban Outfitters are located.

Then, head back to the heart of the Flats and end your day with a nightcap. Dee’s Café (1316 E. Carson St., 412/431-1314, www.deescafe.com [8]) is one of Pittsburgh’s best dive bars, but for a great selection of microbrews and a more clean-cut atmosphere, try Fat Heads (1805 E. Carson St., 412/431-7433, www.fatheads.com [9]), which also serves wonderful salads and sandwiches.

Day 2

If you’re staying Downtown, walk to the nearby Strip District for breakfast. Locals will warn you not to miss DeLuca’s Restaurant (2015 Penn Ave., 412/566-2195) which is without a doubt the city’s most legendary breakfast spot. After your umpteenth cup of bottomless coffee, work off some of those carbs by taking a stroll through Downtown and into Point State Park (101 Commonwealth Pl., 412/471-0235 (park), www.dcnr.state.pa.us/stateParks/parks/point.aspx [10]).

Use the pedestrian walkway on the Fort Duquesne Bridge to cross over the Allegheny River. If you’ve got the energy for a long walk, follow the Three Rivers Heritage Trail (www.friendsoftheriverfront.org [11]) as far as your heart desires. (The path ends near the 40th Street Bridge.) Descend the stairs at the opposite end of the Fort Duquesne Bridge, and you’ll be in the North Shore.

Head to the nearby Andy Warhol Museum (117 Sandusky St., 412/237-8300, www.warhol.org [12]), which, aside from having a great gift shop and a rotating schedule of fascinating temporary exhibits, is the largest single-artist museum in the United States. The Warhol also has a surprisingly good basement café, which is a decent choice for lunch. Before leaving, get directions to the nearby Mattress Factory (500 Sampsonia Way, 412/231-3169, www.mattress.org [13]), a world-renowned installation museum.

For lunch, try the Euro-influenced American fare at Cassis (900 Western Ave., 412/586-7794, www.cassispittsburgh.com [14]). (If you’re traveling with a canine companion, your four-legged friend is welcome in the patio seating area.) After lunch, walk to the National Aviary (Allegheny Commons West Park, 412/323-7235, www.aviary.org [15]) in West Park—with a family of more than 600 feathery friends, it’s the only nonprofit bird zoo in the country.

If you still have energy, spend the rest of the afternoon exploring the Oakland neighborhood. Spend some time at the Carnegie Museums of Art and Natural History (4400 Forbes Ave., 412/622-3131, www.cmoa.org [16], www.carnegiemnh.org [17]), and, if the sun is shining, visit Schenley Park and its Phipps Conservatory (1 Schenley Park, 412/622-6914, www.phipps.conservatory.org [18]).

For dinner, head back into Downtown. Take a cab if the weather is chilly, or go by foot across one of the Three Sisters Bridges (www.pghbridges.com [19])—also known as the only trio of near-identical bridges in the country. All three are self-anchored suspension bridges and are painted Aztec gold. Your destination is Cafe Zao (649 Penn Ave., 412/325-7007), located next door to the O’Reilly Theater. Owned by the same people responsible for the legendary but now shuttered Baum Vivant, Cafe Zao is a perennial hit with the theater crowd for good reason—the Portuguese entrées here are probably the finest in the tri-state area.

After dinner, take in a show in the Cultural District. Pick up a free copy of Pittsburgh City Paper to see what is in production. If nothing grabs your interest or you’d prefer a less expensive and more intimate entertainment option, head back to the South Side via taxi and stop in at Club Café (56 S. 12th St., 412/431-4950, www.clubcafelive.com [20]), which usually offers two pop or folk concerts nightly. (Ask your cabbie to take the 10th Street Bridge from Downtown, which can also be crossed on foot.)