Guide to Pittsburgh's Holiday Markets, Festivals, and Shopping: Celebrate the Season!

Guide to Pittsburgh's Holiday Markets, Festivals, and Shopping: Celebrate the Season!

Pittsburgh transforms into a winter wonderland during the holiday season, with festive markets and events that capture the magic of this time of year. Whether you're looking for unique gifts, delicious seasonal treats, or memorable experiences, these local favorites are must-visits for residents and visitors alike! 

1. Highmark Light Up Night

Highmark Light Up Night in Downtown Pittsburgh, with lights and festive atmosphere

Source: Downtown Pittsburgh Holidays

Location: Downtown Pittsburgh
When: Saturday, November 23, 2024

Kick off the holiday season with Pittsburgh’s iconic Light Up Night! This free event features dazzling light displays, live music, and a spectacular fireworks finale. Wander through downtown to see holiday decorations, pop-up events, and food vendors. It’s the perfect evening to soak in the festive atmosphere.

Pittsburgh Light Up Night Events and Programming

2. Peoples Gas Holiday Market - Celebrating 13 Years!

Peoples Gas Holiday Market in Market Square, Downtown Pittsburgh

Source: Downtown Pittsburgh Holidays

Location: Market Square, Downtown Pittsburgh
When: Nov. 22 - Dec. 24, 2024

This European-inspired market is the heart of Pittsburgh's holiday season. Stroll through the wooden chalets filled with handcrafted goods, unique ornaments, and artisanal foods from local and international vendors. The twinkling lights, live performances, and the iconic giant Christmas tree make it a magical destination. Don’t forget to visit Santa in his stunning, larger-than-life house!

Peoples Gas Holiday Market Events and Programming

3. Handmade Arcade

Location: David L. Lawrence Convention Center

Support local artisans and find one-of-a-kind gifts at the Handmade Arcade, Pittsburgh’s largest independent craft fair. Featuring over 200 vendors, this event is a paradise for those looking for unique jewelry, home goods, artwork, and more. Plus, enjoy workshops and demonstrations that bring the creative process to life. It's the perfect way to support small businesses during the holiday season!

Check out the vendor list

4. Phipps Conservatory’s Winter Flower Show and Light Garden - Kim and Alyssa's Favorite!

Phipps Conservatory Winter Flower Show, illuminated garden Phipps Conservatory festive holiday lights display

Location: Oakland
When: November 16 to January 5, 2025

Phipps Conservatory’s Winter Flower Show and Light Garden holds a special place in our hearts. We love the glowing light displays and family-friendly experiences. Wander through gardens illuminated with glowing orbs, twinkling lights, and seasonal blooms. This annual event offers a magical experience for all ages, blending the beauty of nature with festive cheer.

Phipps Conservatory Holiday Magic Event

5. Dazzling Nights at Pittsburgh Botanic Garden

Pittsburgh Botanic Garden Dazzling Nights, illuminated flowers and lanterns

Source: @pghbotanicgarden

Location: Oakdale
When: November 24 to January 1, 2025

Immerse yourself in a botanical wonderland at the Pittsburgh Botanic Garden's "Dazzling Nights." This event transforms 65 acres into a luminous experience, featuring over 2,000 illuminated flowers, handcrafted lanterns, and interactive light displays. Enjoy festive food and beverages throughout the garden for a unique experience for all ages.

Get tickets

6. Pittsburgh Holiday Pop-up Bars

Pittsburgh's holiday season is illuminated by a variety of festive pop-up bars, each offering unique experiences that capture the city's vibrant spirit. Here's a curated list of must-visit holiday bars in Pittsburgh:

1. Sippin Santa

  • Location: 490 Wood St., Pittsburgh, PA 15222 (next to Capital Grill)
  • Description: Brought to you by the creators of Miracle on 6th, Sippin Santa offers festive glassware, incredible cocktails, and the most festive vibes in the city.
  • More Information: Sippin Santa

2. Wigle Wonderland Holiday Pop-Up

  • Location: 2401 Smallman St., Pittsburgh, PA 15222
  • Description: Opening on November 16, 2024, this pop-up showcases Wigle's newly finished bar at their distillery, illuminated with dazzling lights. Enjoy a Rudolph's Red Nose shot out of an ice skate shot glass or sip a beautifully hued Blue Christmas 75.
  • More Information: Wigle Whiskey

3. Winter Warmer Pop-Up at Square Cafe

  • Location: 134 S Highland Ave, Pittsburgh, PA 15206
  • Description: Lights twinkle as guests enjoy seasonal lattes and adult hot chocolates (spiked with the spirit of your choice) at this new pop-up. It's an ideal spot to relax and grab a holiday drink while exploring East Liberty.
  • More Information: Square Cafe

4. Holiday Tavern at The PA Market

  • Location: 108 19th St., Pittsburgh, PA
  • Description: The first floor of this European market in the Strip District has been tastefully transformed into a rustic winter wonderland. Sip classy cocktails with gold coin and candy cane garnishes, and follow their holiday gift guide to shop and sip all in one place.
  • More Information: The PA Market

For a comprehensive guide to Pittsburgh's holiday pop-up bars, visit Visit Pittsburgh's Holiday Pop-Up Bars.

7. Holiday Shopping in Shadyside

Source: @apricotlanepgh

For a charming holiday shopping experience, head to Walnut Street in Shadyside, one of Pittsburgh's most vibrant shopping districts. This picturesque street is lined with boutiques, specialty shops, and local businesses that offer unique and thoughtful gifts for everyone on your list. By shopping here, you’re not only finding one-of-a-kind treasures but also supporting small businesses that are the backbone of our community.

Here are some must-visit stores to explore:

  • Apricot Lane Pittsburgh: A trendy boutique offering stylish women’s clothing, accessories, and gifts. It’s the perfect spot to find unique holiday outfits or presents for the fashionistas in your life. Follow them on instagram for exclusive specials and deals! (@apricotlanepgh)
  • Kards Unlimited: A gift shop filled with holiday cards, novelty items, and stocking stuffers that are sure to bring a smile. A ton of options for unique gift giving year round.
  • Prantl's Bakery: No holiday shopping trip is complete without a stop at this iconic bakery. Pick up their famous Burnt Almond Torte or seasonal treats to sweeten your celebrations.

8. Lawrenceville Cookie Tour

Lawrenceville Cookie Tour event with shops and holiday treats

Source: The Lawrenceville Cookie Tour

Location: Lawrenceville Neighborhood
When: December 14 and 15

Combine your love for cookies and local shopping during this annual event. Explore Lawrenceville’s charming small businesses while collecting holiday cookies from participating shops. It’s a delicious way to support local and embrace the holiday spirit.

Lawrencevile Cookie Tour Event info

Why These Events Matter to Pittsburgh

These holiday markets and festivals don’t just bring joy—they strengthen community connections and support local businesses. As real estate professionals, we're passionate about highlighting what makes Pittsburgh a special place to live, work, and celebrate. These events showcase the city’s charm, making it a fantastic place to call home. Did we miss any events worth noting? Let us know so we can add it to our list!

Whether you’re a long-time Pittsburgh resident or considering a move to the area, experiencing these festive events will make your holiday season unforgettable. If you’re thinking about buying or selling a home this season, let’s connect to discuss how the Pittsburgh community can be your perfect backdrop.

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Whether you're looking to buy, sell, or simply explore the Pittsburgh area, our team is here to guide you every step of the way. We’re passionate about helping our clients find the perfect home and connecting them with the vibrant communities that make Pittsburgh special. Ready to take the next step?

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