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6. Sledding Hill
During the summer, Flagstaff Hill is crowded with students and tourists, who favor either the calming delights of sun-bathing and picnicking or the more rollicking joys of ultimate Frisbee. Although Pittsburgh gets frigid in winter, there's nary a snowy day that you won't find sledders careening down the hill on their stomachs, screaming gleefully. Pittsburgh isn't famous for its solid snow-cover, and freezing rain doesn't make for good tobogganing, but on the whiter days, you can bet on Flagstaff for good sledding and good company. Granted, Flagstaff is a pretty tame hill for a city built on breakneck slopes, so the pleasure stems more from community: The daring broods of kids in their tea-cup–shaped sleds rotating around as they descend into wipeout mode, and every so often, a band of CMU students flying down the escarpment in full-fledged white-water kayaks.
Flagstaff Hill
Schenley Park at Schenley Drive
7. Jeans Shop
Located in a historic building just across the Birmingham Bridge, Pittsburgh Jeans Co. looks like a throwback to a folksy general store both inside and out. But the shelves of the charming space are lined with the ultimate in premium denim, with the latest trends from more than 40 hot designers. When it comes to denim, it's all about getting the right fit, and this place has professionally trained fit specialists to help you find it. Free alterations are offered to preserve the jeans' original hem.
Pittsburgh Jeans Co.
2222 E. Carson St., South Side
412/381-5326
8. Outdoor Ice Rink
It doesn't have the special holiday flair of the downtown ice rink–no skyscrapers rising around the perimeter, no colossal coniferous tree–but North Park's rink is a local family tradition and has been for years. Unhindered by hockey teams, the rink is open nearly every cold day of winter, with the exceptions of Mondays and holidays, as long as the air is cold enough to keep the ice frozen (warm fronts are the only peril of the outdoor ice rink). "Family Skate" nights are open to adults and up to four children per couple, and the "Sweetheart Couples Skate" is a Valentine's Day favorite. Also,if you're a bit rusty in the skating department, try a round of learn-to-skate lessons for free.
North Park
724/935-1280
9. Nontraditional Comedy Club
The proprietors of the former Deek magazine don't do much for the light-hearted. Their publication was a guerilla-warfare version of the alternative news magazine. So it's not surprising that Deek Comedy Nights at The Shadow Lounge, which are still kickin', come complete with warning from Lounge owner Justin Strong: "If you get offended easily, you probably better just stay home." Four local comedians get a chance to share their wares on the third Monday of each month in the nontraditional, noncomedy-club environment of the Lounge.
Deek Comedy Nights at The Shadow Lounge
5972 Baum Blvd., East Liberty
412/363-8277
10. Happy Hour
It's 5 o'clock and you need a drink. In fact, after the day you've had, what you really want is an ice-cold martini and a distractingly hot bar scene. Head to this lively South Side destination on weekdays (Mon.-Fri., 5-7 p.m.), and you're in luck, whether you belly up to the vast sushi bar or perch at the see-and-be-seen tables. Who doesn't feel happier at Nakama when all cocktails are $1 off and appetizers are half-price? Heads up: If you're wearing un-cool office clothes, consider checking them at the door - as the evening progresses, this singles-friendly bar scene is anything but suit and tie.
Nakama
1611 E. Carson St., South Side
412/381-6000
11. Floating Transportation
Pittsburgh and Venice have long competed for the title of "City With the Most Bridges." With the creation of the River Shuttle, operated by the Port of Pittsburgh, the cities can now also argue about which place has the most charming water taxis. Venice will probably win this one - who can beat those gondolas plying through the narrow canals - but our River Shuttle's service to Station Square, the Point and the North Shore is surprisingly convenient during crowded festival times, when all you want to do is get from one riverbank to the other without joining downtown's gridlock traffic. And you can't beat the price ($8 for an all-day pass), and because the catamaran holds 49 passengers, there's almost always an available seat. Take that, Venice.
River Shuttle
412/874-7707
12. New Pastry Shop
Pastries-A-La-Carte owner Kathy Battis isn't afraid of a little work. That's probably why her labor-intensive pastries - which often take two full days to prepare from scratch - are so popular. Although the high-end pastry shop has been open only since 2004, customers already have favorites, one of which is the Georgia Peach: two homemade vanilla cookies filled with peach-schnapps-flavored cream, dipped in peach-schnapps syrup, then rolled in sugar and completed with a decorative leaf. Attention to presentation and detail is visible in everything that's offered, from the 30-plus cookie varieties to the best-selling burnt-almond raspberry torte, to breakfast pastries such as pecan rolls, bear claws, cinnamon sticks and fruit turnovers.
Pastries-A-La-Carte
81 Clairton Blvd., Pleasant Hills
412/653-2236
13. Cocktail Bar
This chic cocktail lounge set in a glamorously revamped historic firehouse gets all the important details right: the ambient lighting flatters everyone, the low-slung crimson banquettes invite you to linger, and the mixologists behind the bar can turn out great renditions of everything from exotic martinis to classic gin-and-tonics. Firehouse Lounge (in the Strip) also has an appetizing menu of bar nibbles, an appealing outdoor terrace and quite a lineup of events, from theme nights like "Martini, Manicure and Makeovers" to DJs spinning house music on the outdoor deck on the weekends. Needless to say, come and you're likely to stay a while.
Firehouse Lounge
2216 Penn Ave., Strip District
412/434-1230
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