Penn Hills Christmas Events & Things to Do 2025

Immerse yourself in the festive spirit at the Greater Pittsburgh Arts & Crafts Holiday Spectacular. This vibrant event features over 300 booths brimming with stunning arts, unique crafts, and delicious pre-packaged foods. Discover handmade holiday decor, find one-of-a-kind gifts, and indulge in gourmet treats and festive fashion.

Discover the Krampus Holiday Marketplace, a unique event featuring local vendors offering crafts, gifts, and decor with a spooky and festive twist. Visitors can capture memorable photos with Krampus himself on his throne. Children 12 and under receive free admission with an adult.

Step into a magical European and World-themed Christmas market at the Monroeville Convention Center. Discover unique gifts and artisan crafts, then immerse yourself in the festive 'Snoopy's Tasting Tavern,' a Charlie Brown-themed pop-up bar offering seasonal drinks and treats. This indoor celebration promises a unique holiday experience with live music...

Experience the magic of the Peoples Gas Holiday Market, a vibrant European-style bazaar in Downtown Pittsburgh. Discover unique, handcrafted gifts from local makers and international artisans, offering a charming atmosphere for festive shopping. It's the perfect place to find special treasures and soak in the holiday spirit.

Step into a magical European-style holiday market in the heart of Downtown Pittsburgh. The Peoples Gas Holiday Market™ offers a delightful shopping experience with over 100 vendors showcasing unique, handcrafted gifts from local makers and artisans around the world. Find that perfect, one-of-a-kind present while soaking in the festive international...

Discover the 14th annual Holiday Extravaganza presented by the Hampton Band Association. This festive event features over 150 vendors offering a wide array of shopping opportunities, a delightful cookie walk with homemade treats, and live band performances. Children can enjoy a special zone with Santa, Buddy the Elf, crafts, and...

Discover a magical holiday experience at the Winter Market & Holiday Celebration in Uptown Mt. Lebanon. This festive event transforms Washington Road into a bustling marketplace filled with regional artisans, seasonal treats, and unique handcrafted gifts. Visitors can enjoy visits with Santa, an Elf Scavenger Hunt, a model railroad, and...

Canonsburg's Old Fashioned Christmas transforms the town into a 'Hallmark movie-esque' destination, drawing over 25,000 visitors. Explore three market areas with over 60 vendors offering handmade crafts, jewelry, and decor. Don't miss the magical Annual Tree Lighting with Santa, and delight in a global food court. Kid's activities, including games...

Hop aboard a festive BYOB trolley for a magical journey through Pittsburgh's most dazzling holiday lights and landmarks. Starting at Tom's Watch Bar, this 3-hour tour offers a unique way to experience the city's yuletide spirit, complete with music, trivia, and prizes. Bring your own beverages (21+) and prepare to...

Experience the magic of the holidays with a spectacular drive-in laser light show at North Park. This unique event features a dazzling 40-minute display of lights and synchronized holiday music, all enjoyed from the comfort of your own vehicle. Multiple showtimes are available each evening, offering a festive and memorable...

Experience the magic of the holidays at Fun Fore All's Holiday Lights Mini Golf. This beloved event transforms two award-winning miniature golf courses into a dazzling walk-through light display, recognized as one of the best in the region. It's a festive and interactive experience perfect for families looking to create...

Step into a winter wonderland at Enchanted Lights Pittsburgh, a magical holiday stroll through dazzling music and light displays. Enjoy a unique walk-through experience in festive woods, perfect for creating unforgettable memories. Gather around crackling campfires for s'mores and hot chocolate, and savor seasonal treats and craft cocktails. This outdoor...

Experience a unique holiday musical performance featuring a brass ensemble. This event promises a festive atmosphere with a focus on instrumental holiday cheer, perfect for those seeking a different kind of seasonal entertainment.

Highmark First Night Pittsburgh is a vibrant New Year's Eve celebration in downtown Pittsburgh. This city-wide event offers a diverse range of entertainment, including community parade workshops, a GBU-Life SING-OFF Competition, and a spectacular fireworks finale. Attendees can explore various performance venues, enjoy festive food and drinks, and witness a...

Glide across the ice at The UPMC Rink at PPG Place, Pittsburgh's premier outdoor skating destination. This expansive rink, larger than the famous Rockefeller Center rink, offers a magical winter experience surrounded by the city's iconic skyline. Enjoy special themed nights, skate rentals, and the festive ambiance of the holiday...

Get ready for the 64th anniversary of Highmark Light Up Night, the iconic event that ignures the holiday spirit in Downtown Pittsburgh. This spectacular celebration marks the official start of the festive season, transforming the city center with dazzling lights and a vibrant atmosphere. Join the community for a memorable...

Create lasting holiday memories at the Santa Photo Experience at Ross Park Mall. This beloved tradition offers families the chance to capture magical moments with Santa Claus. Special 'Caring Santa' sessions are available for children with special needs, ensuring a comfortable and joyful experience for everyone. Reservations are highly recommended...

Get ready for the 2025 holiday season at The Block Northway, where free family-friendly events and activities await. Subscribe to their email list for the latest updates on performances and happenings starting November 15th. Discover a wide array of shops and dining options throughout the venue.

Capture cherished holiday memories with professional Santa and festive mini sessions. Choose between a magical Santa encounter or a stylish holiday backdrop. Weekday 'Stress Less' sessions offer extended time, perfect for families with young children. Book your spot to create beautiful holiday cards and lasting keepsakes.

Join the Township of Pine for their annual Holiday Dazzle celebration! This festive evening promises a spectacular fireworks display, delicious food truck offerings, enchanting carriage rides, and a special visit from Santa and his elves. Don't miss the chance to enter the Gingerbread House Contest and showcase your holiday creativity.

Bring the whole family for a magical morning at Shady Elms Farm's Breakfast with Santa & Mrs. Claus. Enjoy a delicious breakfast buffet, meet Santa and Mrs. Claus for photos, and let the little ones join festive milk and cookies workshops. It's a heartwarming way to kick off the holiday...