The Jingle Bar on Market Square. Photo by Sally Quinn.

We’ve made it easy for you to experience the best holiday sights and traditions throughout Downtown with a Holiday Happy Hour Hike. You’ll find simple step-by-step directions, plus lots of photo opps, breaks for cocktails and a bit of noshing along the way. The circular route ends just a couple of blocks from the beginning.

The Highmark Tree has hugged the corner of the former Joseph Horne Dept. Store since 1953. Photo by Sally Quinn.

1. Highmark Tree

Start your hike with the brilliant benchmark of Pittsburgh holidays at the corner of Stanwix Street and Penn Avenue. Look up at the six-story lighted tree hugging the corner of the Highmark Building, formerly the Joseph Horne Co. department store. Pittsburghers have been loving that sight since 1953. The tree glows with more than 2,500 lights and about 2,000 oversized ornaments.

Head up Penn Avenue to Sixth Street, make a right at Heinz Hall and continue to the corner at Liberty Avenue and the Heinz Hall Courtyard.

The Holiday KidsPlay Selfie Garden fills the Heinz Hall Courtyard. Photo by Sally Quinn.

2. Holiday KidsPlay Selfie Garden

The whimsical lighted Holiday KidsPlay Selfie Garden is intended for kids at heart, not just little kiddos. Wander through to snap pics with cutouts of favorite TV characters from Fred Rogers Productions. Daniel Tiger, Donkey Hodie and the Odd Squad welcome visitors to sidewalk game challenges, too. Scan the QR codes to access activities and other cool stuff. Gates remain open nightly until 8 p.m., except for Sundays when they close at 6 p.m.

From the courtyard opening, head left on Liberty Avenue to EQT Plaza.

The World’s Largest Pickle Ornament. Photo by Sally Quinn.
The World’s Largest Pickle Ornament. Photo by Sally Quinn.

3. World’s Largest Pickle Ornament

You can expect no less from the city that dedicates an entire weekend to the annual Picklesburgh festival. The 35-foot inflated Heinz Pickle ornament is suspended above EQT Plaza at just the right height for fun photos. After last season’s pickle disaster — the pickle balloon ripped and deflated shortly after its debut — we hope this year’s giant pickle is up to the task.

The tradition of hiding a pickle ornament in your tree comes from German-American beginnings. The reveler who finds the pickle ornament is rewarded with a small gift, a year of good luck or the option to open the first present.

Gates to the three-story pickle are open until 9 p.m. daily for all your selfie needs. Share your pics with #PickleOrnamentPGH to join fellow pickle-loving people.

Walk on a bit farther to 705 Liberty Ave.

Holiday chaos sets the scene at Miracle on Liberty. Sunglasses are optional. Photo by Sally Quinn.

4. Miracle on Liberty

Open the door to the hyper holiday décor of Miracle on Liberty, where every inch is strung with lights, shining ornaments, candy canes and tinsel. The seasonal pop-up returns with the kind of merrymaking that can transform any Scrooge into a Tiny Tim. A bit of imbibing can’t hurt with concoctions like the Christmas Carol Barrel, Snowball Old-Fashioned and the Yippie Kay Yay.

Miracle is run by the folks behind The Warren Bar & Burrow, which serves its bar menu here, too. Share the Crab Rangoon Dip, Grilled Burrata and Pimento Cheese Fries. Or opt for heartier fare, like a Chicken N’Bourbon Sandwich or Yinzer Steak Sammie.

The whole enterprise, which opens at 4 p.m. daily through Dec. 31, raises money for a variety of charities. Miracle management reminds patrons that glassware is available for purchase. Please do not walk away with your glass.

And now, with rosy cheeks and a gleam in your eyes, cross Liberty Avenue to hike up Seventh Avenue to William Penn Place for a completely different holiday atmosphere.

Enjoy a Downton Abbey fantasy in the Grand Lobby of the Omni William Penn Hotel. Photo by Sally Quinn.

5. Omni William Penn Hotel

When the grandeur of an old-fashioned Christmas is more to your taste, find a seat in the Grand Lobby of the Omni William Penn Hotel. This elegant setting appears much as it did upon opening in 1916 with green palms amid sofas, comfy chairs and polished side tables. Dazzling Bohemian crystal chandeliers compete with the towering Christmas tree lights. We know the Dowager Countess would feel quite at home in this room that could double as a set from Downton Abbey.

Relax with a seasonal cocktail or toast with a flute of bubbly. The evening bar menu includes shareable apps, sandwiches and desserts like a toffee brownie with whiskey cream and root beer syrup. Savor your choices while soaking up the classy atmosphere.

On your way out, stop to admire the replica gingerbread hotel constructed by the William Penn chefs.

From the front doors, go to your right toward Sixth Avenue and make a right turn toward Grant Street. Cross Grant to the Steel Plaza.

The Pittsburgh Creche at the Steel Plaza. Photo by Sally Quinn.

6. Pittsburgh Creche

Just behind the mini forest of lighted trees at the Steel Plaza, you can’t miss the larger-than-life sculptures that populate the Pittsburgh Creche. This annual display debuted on Dec. 6, 1999, as the only authorized replica of the Vatican’s Nativity scene in Rome.

As a project that brought the community together, local companies and unions contributed to the original construction, including the Civic Light Opera’s construction center. The manger was designed by Vatican architect Umberto Massana. Vatican sculptor Pietro Simonelli crafted the statues that include the Holy Family, Three Wise Men, a shepherd and an angel.

The Creche is a sight to behold during the Christmas season. It remains on view until the Epiphany on Jan. 6.

Travel along Grant Street past the glowing alcoves and lineup of trees that front the Allegheny County Courthouse to the City-County Building.

Pittsburgh’s Official Christmas Tree. Photo by Sally Quinn.
Pittsburgh’s Official Christmas Tree. Photo by Sally Quinn.

7. City-County Building

This year, Pittsburgh’s Official Christmas Tree in front of the City-County Building comes with a homecoming story of its own. The 45-foot blue spruce was growing a few blocks away outside The Pennsylvanian until being dug up during a landscape renovation project. Employee Chris Fuga took the tree home and transplanted it in his Lincoln Place yard. More than 20 years later, Fuga donated the tree, which returned to its Downtown roots.

Erecting a Christmas tree at Pittsburgh’s seat of government is a tradition that began at the construction site of the City-County Building in 1915. Visitors can search for their neighborhood through the 90 district ornaments.

Be sure to check out the winning Gingerbread House Contest entries on display behind glass in the portico. The creative cookie structures built with frosting glue and decorated with everything from candy canes to pretzels and gumdrops will inspire you to compete next year.

Cross Grant Street and follow Fourth Avenue to the shining glass towers of PPG Place.

Sally Quinn

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