The Jingle Bar on Market Square. Photo by Sally Quinn.
The UPMC Ultimate Christmas Tree Experience at the UPMC Ice Rink in PPG Plaza. Photo by Sally Quinn.

8. The UPMC Rink at PPG Plaza and the UPMC Ultimate Christmas Tree Experience

This season marks the 20th year for the PPG Place ice skating rink, which opened in 2001. The rink holds bragging rights with a size that’s 67 percent larger than the more famous ice rink at Rockefeller Center.

We like to think our rink’s new Christmas tree centerpiece is more spectacular, too. The 66-foot, technologically advanced tree is equipped with more than 10,000 high-resolution LED lights that are programmed to create an amazing display of patterns and colors that are choreographed to music.

Check out the reflection of the lights in the mirror walls of PPG Place, and you’ll agree that this is a must-see spot even for those who don’t care to lace up their skates.

From the ice rink, follow Market Street toward Market Square. Peek in the windows at Two PPG on your left to view the Spirits of Giving display featuring Santa-like figures from around the world.  Make a left when you reach Market Square and follow around the square to the right for your next holly jolly stop.

The Jingle Bar ramps holiday decorations into overdrive. Photo by Sally Quinn.

9. Jingle Bar

The Jingle Bar returns in its fourth year to set up shop at 25 Market Square. Climb the gift-wrapped stairway to the second floor where the bar is a bright chaotic scene of blinking lights, shelves dripping with fake snow and dangling snowflakes. The opposite wall is filled with a lineup of blinking, clanging pinball machines.

The bar menu offers “sauce for the season” with themed cocktails like the Russian Reindeer Mule, Cocoa Prancer and Santa’s 75, a delightful mix of Bombay Sapphire, chamomile, elderflower, citrus and bubbles.

There’s plenty of room for dancing to DJ spins, karaoke and live music on weekends. Order snacks delivered from next door’s Slider Vibes via a QR code. The Jingle Bar opens at 4 p.m. on weekdays and noon on Saturdays and Sundays.

Look no farther than across the cobblestone street to dive into the European-style marketplace.

The Sphere Tree towers over the People’s Gas Holiday Market. Photo by Sally Quinn.
The Sphere Tree towers over the People’s Gas Holiday Market. Photo by Sally Quinn.

10. People’s Gas Holiday Market

The village of wooden chalets at People’s Gas Holiday Market is packed with vendors selling distinctive wares. Expect handcrafted jewelry, photographic prints and puzzles, fused glass and mosaics, intricate ornaments and a diverse collection of children’s books. Shop for international gifts from Germany, Spain, Poland and Ireland. There’s good holiday snacking as well, including strudel, roasted nuts, truffles and toffee.

Enjoy live happy hour music at the BJ’s Sounds of the Season Stage. And stop for photos at the 35-foot Sphere Tree, a beautiful backdrop of glowing red and white lights.

The Holiday Market is open until 8 p.m. Mondays-Thursdays, until 9:30 p.m. on Fridays and Saturdays and until 6 p.m. on Sundays through Dec. 23.

Leave Market Square and head back to Market Street. Make a stop at number 435 Market St.

Hot stuff at the Ski Lodge. Photo courtesy of Creatives Drink.

11. Ski Lodge at Market St. Grocery

You’ll find this hot stuff pop-up “bar” in front of Market Street Grocery, where gas fire pits and seating are set up. Wrap your hands around a hot toddy that warms from the inside and bask in the fire pit heat on the outside. As an outdoor venue, weather can be a bother. Check Creatives Drink’s Facebook page for opening times and dates.

Follow Market Street toward Liberty Avenue and stop in the Fairmont Pittsburgh Hotel.

The lobby at the Fairmont Pittsburgh Hotel. Photo by Sally Quinn.

12. Fairmont Pittsburgh Hotel

Even grownups have secret holiday wishes. Take advantage of the Santa’s mailbox in the Fairmont Pittsburgh hotel lobby. Forgot your letter at home? No problem. You’ll find a table with special stationery to compose your note to Santa. If that wish includes one more stop for a nibble and sip, head upstairs to fl.2 (Floor 2) and find a seat at the shining oval bar. Expect fresh, locally sourced ingredients and spirits at this great spot to unwind.

And your Holiday Happy Hour Hike is now complete. Cheers!

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Sally Quinn

Sally Quinn is a Pittsburgh-based editor and writer who writes about food, entertainment, kid stuff, pop culture, cocktails!