Holiday Event Guide: How Pittsburgh Is Prepping for Festive Cheer

PHOTO BY DAVE DICELLO

With Halloween in the rearview mirror and the holiday season quickly approaching, the City of Pittsburgh has turned its attention to twinkling lights and festive fun. 

At a press conference on Nov. 5, officials with the Pittsburgh Downtown Partnership unveiled their plans for the city’s 2026 holiday season, which include two significant milestones: 65 years of Highmark Light Up Night and 15 years of the People’s Gas Holiday Market.

The popular traditions, along with new attractions, are expected to draw thousands to the city center to support local businesses, restaurants and artists. 

“We take the holidays very seriously in Pittsburgh,” says Jeremy Waldrup, president and CEO of the Pittsburgh Downtown Partnership, in a statement.

He adds that last year, more than 3.1 million people came to Downtown throughout the holiday season. For 2026, the festivities officially begin on Nov. 20 with the city’s Grand Opening Day Celebration, which includes the opening of the Holiday Market in the newly renovated Market Square. 

“For the last 15 years, Peoples has had the honor to support Downtown and small businesses through its sponsorship of the Holiday Market,” Peoples president Michael Huwar says in a statement. “I can’t think of a better way to celebrate this anniversary year than returning to a revitalized Market Square for shopping, entertainment and making new holiday memories.”

Light Up Night, slated for Nov. 21, will celebrate its 65th anniversary this year. According to a 2010 Pittsburgh Magazine article, the event was first celebrated in 1960; all lights Downtown were switched on at exactly 6 p.m. as department stores revealed their holiday displays.

Now, Light Up Night draws between 70,000 and 90,000 people annually.

“For 65 years, Highmark Light Up Night has been a cherished tradition that brings people together and showcases the spirit, pride and resilience of our city,” says David Holmberg, CEO of Highmark Health, which has sponsored the event since 2021. 

Light Up Night’s festive footprint will also include Arts Landing, which will serve as the new home for the annual Xfinity Holiday Jam, where headliner Daya will perform as part of Light Up Night celebrations on Nov. 21. Light Up Night will also usher in a new, free light experience at Arts Landing called Winter Glow, a “vibrant seasonal destination where light, art and atmosphere create moments of warmth, wonder and discovery in the heart of Downtown Pittsburgh,” according to a press release.

The event schedule is as follows: 

GRAND OPENING DAY | FRIDAY, NOV. 20 

Those who can’t wait for Light Up Night® can start their holiday shopping early at the Grand Opening of the Peoples Gas Holiday Market on Friday, November 20, as it makes its return to the newly modernized Market Square. 

Opening at 11 a.m., this year’s Peoples Gas Holiday MarketTM features chalets brimming with one-of-a-kind wares from local makers along with gifts created by artisans from around the world. The Market will remain open daily through Christmas Eve, with extended hours in the final week. 

Starting at 5 p.m., a series of fast-paced games presented and hosted by local favorites YaJagoff will take place. From bingo to gift-wrapping challenges, contestants will kick off the holiday season in a suitably “yinzer” way, officials say.

HIGHMARK LIGHT UP NIGHT | SATURDAY, NOV. 21 

Highmark Light Up Night® returns for its special 65th anniversary in Downtown with tree and bridge lightings, two stages of live music, craft food vendors, festive shopping experiences and “supersized” fireworks. Light Up Night 2026 takes place the Saturday before Thanksgiving, starting at 4 p.m. 

LIGHT UP NIGHT HIGHLIGHTS: 

Tree lightings, illuminated bridges and supersized fireworks kick off the holiday season with a traditional Pittsburgh bang: 

5 p.m. | City-County Building: City of Pittsburgh’s Tree Lighting with Zambelli Rooftop Fireworks The City of Pittsburgh’s Official Christmas Tree for 2026 is a 38-foot-tall Blue Spruce provided by a local family in Brighton Heights. The tree, which is Downtown’s only live evergreen, will be on display on the Grant Street Portico of the historic City-County Building through early January. Musical performances, light shows, a craft market, and the Gingerbread House Display accompany the City’s 113th annual tree lighting. 

5:30 p.m. | Point Park University Pittsburgh Playhouse: Yuletide! A Holiday Spectacular

Enjoy a special preview of a new musical, Yuletide! A Holiday Spectacular, that takes spectators on a magical journey through heartfelt humor, music and dance while acting as a reminder for the true reason of the season. 

6 p.m. | PPG Plaza: UPMC Ultimate Holiday Tree Lighting and American Cancer Society Tribute of Light Celebration 

This high-tech, energy-efficient, LED-lit holiday tree performs light shows choreographed to music. At more than 66 feet tall, it features over 100,000 lights and will display musical animation and holiday scenes. 

7 p.m. | Stanwix St. & Penn Ave: Highmark Christmas Tree Lighting with Zambelli Rooftop Fireworks 

The over 100-foot-tall Highmark Christmas “Tree” adorns the corner of the former landmark Horne’s department store with more than 2,500 eco-friendly LED lights and 2,000 ornaments. Plus, look out for a special visit from the Pittsburgh Pirate Parrot during the lighting ceremony. 

PHOTO BY DAVE DICELLO

8 p.m. | Cosmologyscape: A Dream for Pittsburgh, Lighting of the Sister Bridges Roberto Clemente (Sixth Street), Andy Warhol (Seventh Street), and Rachel Carson (Ninth Street) Bridges

Allegheny County, with support from Shiftworks Community + Public Arts, commissioned artists Alisha B. Wormsley and Kite to highlight the iconic Roberto Clemente, Andy Warhol and Rachel Carson Bridges with a light show, Cosmologyscape. It “transforms the written dreams of Pittsburgh greats Rachel Carson, Andy Warhol, Roberto Clemente, Fred Rogers, Thaddeus Mosley, August Wilson, Helen Faison, and Madame Cardwell Dawson, as well as community members, into visual patterns that will be displayed on the bridges during this year’s holiday season,” according to a press release.

8:30 p.m. | Headliner Daya at the Xfinity Holiday Jam at Arts Landing 

A Grammy Award winner before the age of 20, synth-pop innovator Daya earned a double-platinum hit with “Hide Away,” her self-empowered debut single, co-written when she was still in high school. Following its success, she teamed up with the Chainsmokers for “Don’t Let Me Down,” a dance anthem that sold more than 10 million copies in America alone. Daya will bring an energetic crowd-pleasing performance to the Xfinity Holiday Jam, officials say.

9:30 p.m. | Xfinity Fireworks Spectacular with Supersized Zambelli Finale 

Highmark Light Up Night will end with a supersized Grand Finale display by the first family of pyrotechnics, Zambelli Fireworks. 

Free live music will also take center stage with performances across two festive locations: 

Highmark Stage (Penn Ave & Stanwix St) 

4-5:30 p.m. | Confluence Theater of Pittsburgh 

6-7:45 p.m. | Joe Grushecky and The Houserockers 

8:15-9:30 p.m. | Justin Fabus 

Xfinity Holiday Jam (Arts Landing) 

4-6 p.m. | DJ Slim 

6:30-7:45 p.m. | Neon Bridges

8:30-9:30 p.m. | Daya 

Even if you miss out on Light Up Night, visitors to Downtown can also take part in a series of events held across the city all season long:

The Peoples Gas Holiday MarketTM | Nov. 20 – Dec. 24 

The Peoples Gas Holiday MarketTM returns to Market Square, celebrating 15 years of local charm and international flair. Shop among over 30 vendors, including several provided by Sustainable Pittsburgh for handmade ornaments, custom decor, candles, pre-packaged goods and more.

Live Music at Market Square Community Stage 

Presented by Huntington Bank,community groups from throughout the region deliver a diverse selection of soulful sounds, contemporary covers and festive renditions of holiday favorites through the season while shoppers enjoy the Peoples Gas Holiday Market.

Holiday Window Display Competition 

Beginning on Light Up Night, Nov. 21, visitors are invited to stroll through Market Square, admire the festive displays and vote for their favorite storefront window. The winning business will receive a charitable donation to an organization of their choice, making this tradition not only joyful, but meaningful, too.

Santa’s House | Nov. 21 – Dec. 24 

Santa Claus is coming to ‘tahn as he returns to his cozy house in Heinz Hall Courtyard. Santa’s House will open Nov. 21 through Dec. 24, with expanded hours in the final week. 

*Santa’s House will be closed beginning the Saturday after LUN and will reopen on Black Friday. 

Folks can also take a keepsake photo with Santa; Help out neighbors in need this holiday season with a $10 suggested donation to the Greater Pittsburgh Community Food Bank and receive a free digital photo of your visit to share with friends and family. Check DowntownPittsburgh.com/Holidays for hours and other details. 

PHOTO BY RENEE ROSENSTEEL | PITTSBURGH DOWNTOWN PARTNERSHIP

Holiday KidsPlay | Saturdays and Sundays, Nov. 21 – Dec. 20 and Black Friday 

In a new location in Market Square, families will find a variety of indoor Holiday KidsPlay activities sponsored by the local program partner of Dolly Parton’s Imagination Library, Reading Ready Pittsburgh and in partnership with Fred Rogers Productions. 

Every weekend until Christmas, children can enroll in Dolly Parton’s Imagination Library, decorate a Mister Rogers sweater ornament with messages of thanks, make their own ornament, visit with Pittsburgh Pirates mascots, play giant games and settle in for multiple story time offerings, plus relish in craft-making spearheaded by a rotating lineup of local community partners. 

Reading Ready Pittsburgh and the City of Pittsburgh are working together to expand Dolly Parton’s Imagination Library, a book gifting program that mails free, high-quality books to children from birth to age five in the City of Pittsburgh, as well as those living in more than 20 additional zip codes in the Pittsburgh area. There are no household income requirements, and enrollment only takes a couple of minutes, officials say.

Selfie Garden | Nov. 21 – Dec. 24 

The outdoor Heinz Hall Courtyard will once again be transformed into a children’s television dreamland with colorful backdrops and life-sized standees of popular characters from Fred Rogers Productions’ beloved children’s shows and other PBS favorites, including Daniel Tiger’s Neighborhood, Peg + Cat, Donkey Hodie and Odd Squad. 

Ice Skating at the UPMC Rink at PPG Place | Nov. 13 – Feb. 28

Take a break from shopping and lace up your skates at the coolest place downtown, which is surrounded by what officials call “the iconic Crown Jewel” of the Pittsburgh skyline. Celebrating its 26th anniversary, The UPMC Rink at PPG Place will open on Friday, Nov. 13, and remain open daily throughout the holiday season. Reserve online skating sessions at therinkatppgplace.com/ 

Sustainable Pittsburgh Chalet at The Peoples Gas Holiday Market | Nov. 20 – Dec. 24 

Visit Sustainable Pittsburgh’s chalet at the Peoples Gas Holiday Market for an array of eco-friendly offerings from rotating local makers and creators. 

Pittsburgh Crèche | Nov. 20 – Jan. 3 

Visit Pittsburgh’s life-sized nativity scene that models the scene of Christ’s birth and is a replica of the crèche once found out-side of Saint Peter’s Basilica in Rome. This crèche, which measures roughly 64 feet wide by 36 feet long and features 20 life-sized figures, has been connecting Pittsburghers and visitors with the meaning and joy of the Christmas season for over 25 years. It is open to the public Nov. 20 through early January, and a $25 donation per visit is strongly encouraged to support the ongoing maintenance of the exhibit. Each purchaser will be entered into a daily lottery drawing for prizes.

24th Annual Gingerbread House Display & Competition | Nov.  21- Jan. 8 

This beloved Pittsburgh tradition has dazzled thousands of visitors for the past two decades at both PPG Place and the historic City-County Building. The competition returns for a 24th year as houses created by the people of Pittsburgh, the surrounding Allegheny County communities, and beyond will be on display in the Grand Lobby throughout the holiday season.

Highmark Winter Glow: An Arts Landing Light Experience | Nov. 21 – Jan. 10

Explore a vibrant seasonal destination where light, art and atmosphere create moments of warmth, wonder and discovery in the heart of Downtown Pittsburgh. Free and open to all. 

Black Friday | Nov. 27 

Avoid the wild rush of malls and put the holiday back in your holiday shopping. With holiday sights, live music and free family activities around every corner, spending Black Friday in Downtown means more family memories and less stress. Plus, visitors can enjoy a special bonus day of Holiday KidsPlay sponsored by the local program partner of Dolly Parton’s Imagination Library, Santa’s House, live music and craft foods. 

Small Business Saturday | Nov. 28 

This well-known national initiative encourages people to come out the day after Black Friday and support their local economy by shopping at small businesses in the community. With more than 150 small businesses in the Central Business District, Downtown is a great place to show support for the local economy. You’ll find small businesses offering men’s and women’s apparel, home goods, jewelry and more for everyone on your list. 

Downtown Holiday Shopping Trail by Handmade Arcade | Dec. 4 

Selected as a winner of the 2026 Citizen’s Downtown Placemaking Grant, Handmade Arcade’s shopping trail connects Handmade Arcade’s Holiday Market at the Convention Center to the Holiday Market in Market Square. Patrons will get the chance to shop at featured small businesses that sit between these two holiday locations while following the trail map. 

Menorah Lighting | Dec. 4 

On Dec. 4 at 5 p.m., join Mayor Corey O’Connor and community leaders in lighting the giant 12-foot Menorah located in front of the City-County Building. The Menorah serves as a beacon of light, symbolizing freedom and peace for all. The celebration includes live music and Chanukah refreshments of latkes and donuts.