| Event | Venue | Date/Time | |
| Pittsburgh Penguins vs. Anaheim Ducks | PPG Paints Arena
Pittsburgh, PA | Tuesday
12/9/2025
7:00 PM |  |
| Pittsburgh Symphony Orchestra: Messiah | Heinz Hall
Pittsburgh, PA | Tuesday
12/9/2025
7:30 PM | |
| Straight No Chaser | Benedum Center
Pittsburgh, PA | Tuesday
12/9/2025
7:30 PM | |
| Stella Cole | City Winery - Pittsburgh
Pittsburgh, PA | Tuesday
12/9/2025
7:30 PM | |
| Hannah Juanita & Mose Wilson | Club Cafe
Pittsburgh, PA | Tuesday
12/9/2025
8:00 PM | |
| Highly Suspect | Stage AE
Pittsburgh, PA | Tuesday
12/9/2025
8:00 PM | |
| Ryan Davis and The Roadhouse Band | Bottlerocket Social Hall
Pittsburgh, PA | Wednesday
12/10/2025
8:00 PM | |
| Pittsburgh Penguins vs. Montreal Canadiens | PPG Paints Arena
Pittsburgh, PA | Thursday
12/11/2025
7:00 PM | |
| Disciple of the Garden - Tribute to Soundgarden, Audioslave and Chris Cornell | Crafthouse Stage & Grill
Pittsburgh, PA | Thursday
12/11/2025
7:30 PM | |
| Mannheim Steamroller Christmas | Benedum Center
Pittsburgh, PA | Thursday
12/11/2025
7:30 PM | |
| Koffin Kats | Mr Small's Theatre
Pittsburgh, PA | Thursday
12/11/2025
8:00 PM | |
| J Roddy Walston | Mr Small's Fun House
Pittsburgh, PA | Thursday
12/11/2025
8:00 PM | |
| Pittsburgh Ballet Theatre: The Nutcracker | Benedum Center
Pittsburgh, PA | Friday
12/12/2025
7:00 PM | |
| Robert Morris Colonials Women's Hockey vs. Long Island University Sharks | Clearview Arena
Pittsburgh, PA | Friday
12/12/2025
7:00 PM | |
| Matthew West | Amplify Church Pittsburgh East Campus
Pittsburgh, PA | Friday
12/12/2025
7:00 PM | |
| Livefromthecity | Club Cafe
Pittsburgh, PA | Friday
12/12/2025
7:00 PM | |
| Pittsburgh Symphony Orchestra: Daniel Meyer - Highmark Holiday Pops | Heinz Hall
Pittsburgh, PA | Friday
12/12/2025
7:30 PM | |
| Too Many Zooz | Mr Small's Theatre
Pittsburgh, PA | Friday
12/12/2025
8:00 PM | |
| Jay Som | Spirit Hall
Pittsburgh, PA | Friday
12/12/2025
8:00 PM | |
| Polyrhythmics | Thunderbird Cafe
Pittsburgh, PA | Friday
12/12/2025
8:00 PM | |
| Armchair Boogie | The Original Pittsburgh Winery
Pittsburgh, PA | Friday
12/12/2025
8:00 PM | |
| A Musical Christmas Carol | Byham Theater
Pittsburgh, PA | Saturday
12/13/2025
1:00 PM | |
| Pittsburgh Ballet Theatre: The Nutcracker | Benedum Center
Pittsburgh, PA | Saturday
12/13/2025
2:00 PM | |
| Pittsburgh Symphony Orchestra: Daniel Meyer - Highmark Holiday Pops | Heinz Hall
Pittsburgh, PA | Saturday
12/13/2025
2:30 PM | |
| Robert Morris Colonials Women's Hockey vs. Long Island University Sharks | Clearview Arena
Pittsburgh, PA | Saturday
12/13/2025
3:00 PM | |
| Pittsburgh Penguins vs. San Jose Sharks | PPG Paints Arena
Pittsburgh, PA | Saturday
12/13/2025
3:00 PM | |
| A Musical Christmas Carol | Byham Theater
Pittsburgh, PA | Saturday
12/13/2025
6:00 PM | |
| Avery Anna | Stage AE
Pittsburgh, PA | Saturday
12/13/2025
7:00 PM | |
| Pittsburgh Ballet Theatre: The Nutcracker | Benedum Center
Pittsburgh, PA | Saturday
12/13/2025
7:00 PM | |
| Matt Light's Ugly Sweater Party | City Winery - Pittsburgh
Pittsburgh, PA | Saturday
12/13/2025
7:00 PM | |
| Confluence Ballet: The Jazz Nutcracker | Kelly-Strayhorn Theater
Pittsburgh, PA | Saturday
12/13/2025
7:00 PM | |
| Bumpin' Uglies & Ballyhoo! | Mr Small's Theatre
Pittsburgh, PA | Saturday
12/13/2025
7:30 PM | |
| Pittsburgh Symphony Orchestra: Daniel Meyer - Highmark Holiday Pops | Heinz Hall
Pittsburgh, PA | Saturday
12/13/2025
7:30 PM | |
| Lily Henley | The Original Pittsburgh Winery
Pittsburgh, PA | Saturday
12/13/2025
8:00 PM | |
| Matt Light's Ugly Sweater Party | City Winery - Pittsburgh
Pittsburgh, PA | Saturday
12/13/2025
10:00 PM | |
| A Musical Christmas Carol | Byham Theater
Pittsburgh, PA | Sunday
12/14/2025
11:00 AM | |
| Pittsburgh Ballet Theatre: The Nutcracker | Benedum Center
Pittsburgh, PA | Sunday
12/14/2025
12:00 PM | |
| Confluence Ballet: The Jazz Nutcracker | Kelly-Strayhorn Theater
Pittsburgh, PA | Sunday
12/14/2025
2:00 PM | |
| Pittsburgh Symphony Orchestra: Daniel Meyer - Highmark Holiday Pops | Heinz Hall
Pittsburgh, PA | Sunday
12/14/2025
2:30 PM | |
| Pittsburgh Penguins vs. Utah Mammoth | PPG Paints Arena
Pittsburgh, PA | Sunday
12/14/2025
3:00 PM | |
| A Musical Christmas Carol | Byham Theater
Pittsburgh, PA | Sunday
12/14/2025
4:00 PM | |
| Pittsburgh Ballet Theatre: The Nutcracker | Benedum Center
Pittsburgh, PA | Sunday
12/14/2025
4:30 PM | |
| Mary Fahl | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
12/14/2025
7:30 PM | |
| PARKING: Pittsburgh Steelers vs. Miami Dolphins | Acrisure Stadium Parking Lots
Pittsburgh, PA | Monday
12/15/2025
TBD | |
| Premium Tailgate Party: Pittsburgh Steelers vs. Miami Dolphins | Premium Tailgate Tent - Pitt
Pittsburgh, PA | Monday
12/15/2025
TBD | |
| Tailgreeter Tailgate: Pittsburgh Steelers vs. Miami Dolphins | Tailgreeter All-Inclusive Tailgate - Acrisure Stadium
Pittsburgh, PA | Monday
12/15/2025
TBD | |
| Pittsburgh Gold Zone Tailgate: Pittsburgh Steelers vs. Miami Dolphins | Gameday Hospitality - Pittsburgh
Pittsburgh, PA | Monday
12/15/2025
4:30 PM | |
| Pittsburgh Steelers vs. Miami Dolphins | Acrisure Stadium
Pittsburgh, PA | Monday
12/15/2025
8:15 PM | |
| Pittsburgh Penguins vs. Edmonton Oilers | PPG Paints Arena
Pittsburgh, PA | Tuesday
12/16/2025
7:00 PM | |
| The Supersuckers & Scott H. Biram | Crafthouse Stage & Grill
Pittsburgh, PA | Tuesday
12/16/2025
7:00 PM | |
| Jody Nardone Trio: A Charlie Brown Christmas - A Tirbute to Vince Guaraldi | City Winery - Pittsburgh
Pittsburgh, PA | Tuesday
12/16/2025
7:30 PM | |
| Holiday Brass Spectacular | Heinz Hall
Pittsburgh, PA | Tuesday
12/16/2025
7:30 PM | |
| JD McPherson | Thunderbird Cafe
Pittsburgh, PA | Tuesday
12/16/2025
8:00 PM | |
| A Classic Holiday | The Original Pittsburgh Winery
Pittsburgh, PA | Wednesday
12/17/2025
7:30 AM | |
| Pittsburgh Panthers vs. Binghamton Bearcats | Petersen Events Center
Pittsburgh, PA | Wednesday
12/17/2025
7:00 PM | |
| Primer 55 | Crafthouse Stage & Grill
Pittsburgh, PA | Wednesday
12/17/2025
7:00 PM | |
| John Doyle & Cathie Ryan | City Winery - Pittsburgh
Pittsburgh, PA | Wednesday
12/17/2025
7:30 PM | |
| Pittsburgh Panthers Women's Basketball vs. St. Francis (PA) Red Flash | Petersen Events Center
Pittsburgh, PA | Thursday
12/18/2025
6:00 PM | |
| Trisha Yearwood | Heinz Hall
Pittsburgh, PA | Thursday
12/18/2025
7:30 PM | |
| Primitive Man | Thunderbird Cafe
Pittsburgh, PA | Thursday
12/18/2025
8:00 PM | |
| K3ETH | Mr Small's Fun House
Pittsburgh, PA | Thursday
12/18/2025
8:00 PM | |
| Scarhaven | Club Cafe
Pittsburgh, PA | Thursday
12/18/2025
8:00 PM | |
| Pittsburgh Ballet Theatre: The Nutcracker | Benedum Center
Pittsburgh, PA | Friday
12/19/2025
7:00 PM | |
| A Musical Christmas Carol | Byham Theater
Pittsburgh, PA | Friday
12/19/2025
7:00 PM | |
| Pittsburgh Symphony Orchestra: Daniel Meyer - Highmark Holiday Pops | Heinz Hall
Pittsburgh, PA | Friday
12/19/2025
7:30 PM | |
| Big Laughs Year End Showcase | Mr Small's Fun House
Pittsburgh, PA | Friday
12/19/2025
8:00 PM | |
| Zoot - A Jazz & Comedy Showcase | Bottlerocket Social Hall
Pittsburgh, PA | Friday
12/19/2025
8:00 PM | |
| Pleaktunes Trio: A Charlie Brown Christmas Album Live | The Original Pittsburgh Winery
Pittsburgh, PA | Friday
12/19/2025
8:00 PM | |
| Animeverse | David L. Lawrence Convention Center
Pittsburgh, PA | Saturday
12/20/2025
TBD | |
| A Musical Christmas Carol - Sensory Friendly Performance | Byham Theater
Pittsburgh, PA | Saturday
12/20/2025
11:00 AM | |
| Pittsburgh Ballet Theatre: The Nutcracker | Benedum Center
Pittsburgh, PA | Saturday
12/20/2025
2:00 PM | |
| Trans-Siberian Orchestra: The Ghost of Christmas Eve | PPG Paints Arena
Pittsburgh, PA | Saturday
12/20/2025
2:30 PM | |
| Pittsburgh Symphony Orchestra: Daniel Meyer - Highmark Holiday Pops | Heinz Hall
Pittsburgh, PA | Saturday
12/20/2025
2:30 PM | |
| A Musical Christmas Carol | Byham Theater
Pittsburgh, PA | Saturday
12/20/2025
4:00 PM | |
| Pittsburgh Ballet Theatre: The Nutcracker | Benedum Center
Pittsburgh, PA | Saturday
12/20/2025
7:00 PM | |
| Trans-Siberian Orchestra: The Ghost of Christmas Eve | PPG Paints Arena
Pittsburgh, PA | Saturday
12/20/2025
7:30 PM | |
| Pittsburgh Symphony Orchestra: Daniel Meyer - Highmark Holiday Pops | Heinz Hall
Pittsburgh, PA | Saturday
12/20/2025
7:30 PM | |
| Man Made 4EVER Fest | Mr Small's Fun House
Pittsburgh, PA | Saturday
12/20/2025
8:00 PM | |
| This Christmas: A Soul Celebration ft. Kenny Stockard & Cam Chambers | Bottlerocket Social Hall
Pittsburgh, PA | Saturday
12/20/2025
8:00 PM | |
| Animeverse | David L. Lawrence Convention Center
Pittsburgh, PA | Sunday
12/21/2025
TBD | |
| A Musical Christmas Carol | Byham Theater
Pittsburgh, PA | Sunday
12/21/2025
11:00 AM | |
| Pittsburgh Ballet Theatre: The Nutcracker | Benedum Center
Pittsburgh, PA | Sunday
12/21/2025
12:00 PM | |
| Echo - Tribute to Tom Petty | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
12/21/2025
12:00 PM | |
| Pittsburgh Symphony Orchestra: Daniel Meyer - Highmark Holiday Pops | Heinz Hall
Pittsburgh, PA | Sunday
12/21/2025
1:30 PM | |
| A Musical Christmas Carol | Byham Theater
Pittsburgh, PA | Sunday
12/21/2025
4:00 PM | |
| Pittsburgh Ballet Theatre: The Nutcracker | Benedum Center
Pittsburgh, PA | Sunday
12/21/2025
4:30 PM | |
| Rahsaan Patterson | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
12/21/2025
5:30 PM | |
| Pittsburgh Symphony Orchestra: Daniel Meyer - Highmark Holiday Pops | Heinz Hall
Pittsburgh, PA | Sunday
12/21/2025
6:00 PM | |
| Reasons to Rock Showcase | Mr Small's Fun House
Pittsburgh, PA | Sunday
12/21/2025
7:00 PM | |
| Pittsburgh Penguins vs. Montreal Canadiens | PPG Paints Arena
Pittsburgh, PA | Sunday
12/21/2025
7:00 PM | |
| Rahsaan Patterson | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
12/21/2025
8:30 PM | |
| Duquesne Dukes vs. Canisius Golden Griffins | UPMC Cooper Fieldhouse
Pittsburgh, PA | Monday
12/22/2025
7:00 PM | |
| A Musical Christmas Carol | Byham Theater
Pittsburgh, PA | Tuesday
12/23/2025
2:00 PM | |
| Pittsburgh Ballet Theatre: The Nutcracker | Benedum Center
Pittsburgh, PA | Tuesday
12/23/2025
7:00 PM | |
| A Musical Christmas Carol | Byham Theater
Pittsburgh, PA | Tuesday
12/23/2025
7:00 PM | |
| PureSoul - Jazz and Soul Christmas Spectacular | City Winery - Pittsburgh
Pittsburgh, PA | Tuesday
12/23/2025
7:30 PM | |
| The Harlem Globetrotters | PPG Paints Arena
Pittsburgh, PA | Friday
12/26/2025
1:00 PM | |
| The Harlem Globetrotters | PPG Paints Arena
Pittsburgh, PA | Friday
12/26/2025
6:00 PM | |
| Pittsburgh Ballet Theatre: The Nutcracker | Benedum Center
Pittsburgh, PA | Friday
12/26/2025
7:00 PM | |
| The Reckoning - The Music of R.E.M. | City Winery - Pittsburgh
Pittsburgh, PA | Friday
12/26/2025
7:30 PM | |
