Plan Your Perfect Downtown Holiday Weekend

With less than two weeks until the holidays, now is the perfect time to enjoy a winter weekend in Downtown Pittsburgh. Enjoy an illuminated Market Square, shop the Peoples Gas Holiday Market™, and more.

Brunch at Sienna on the Square 🍽️

Start the weekend on the right foot with brunch at Sienna on the Square. Located right in Market Square in the heart of Downtown, Sienna on the Square’s intimate and beautiful space puts you right in the middle of all the holiday activities.

Enjoy a decadent brunch menu that features everything from Lobster Farm Egg Scramble and Pork Belly Hash to Torchio Arrabiata and Baked Roman Gnocchi. Plus, don’t miss signature cocktails, coffee from La Prima, and great appetizers to share. Learn more about this neighborhood staple.

Shop at the Peoples Gas Holiday Market™ 🛍️

After brunch, stroll through a cherished Pittsburgh holiday tradition at the Peoples Gas Holiday Market™ where you’ll find vendors from around the city and around the globe. Find the perfect gift, enjoy live entertainment on the stage, and take a photo with Santa with a donation to the Greater Pittsburgh Community Food Bank.

Ride Around Downtown in Style (for Free) 🎄

A holiday season favorite, enjoy free rides around Downtown on the Fifth Avenue Place Holly Trolley & Horse Drawn Carriage Rides.

On Saturday, take the Fifth Avenue Place Holly Trolley as it loops around Downtown, stopping at all the holiday hotspots while you learn about the neighborhood and hear suggestions on things to do. Stops include the annual Gingerbread Display and Contest at the City-County Building, the Crèche at the U.S. Steel Tower, and Holiday KidsPlay.

Then, on both Saturday and Sunday, enjoy rides in a beautiful, historic horse-drawn carriage around Market Square, picking up and dropping off at PPG Place and presented by Highwoods Properties.

Both are free and do not require tickets or reservations.

Skate Around PPG Plaza ⛸️

Enjoy an exhilarating holiday tradition as you glide and ice skate around the breathtaking 65’ Christmas Tree in the center of the MassMutual Pittsburgh Ice Rink in Downtown Pittsburgh.

More holiday fun continues all season long 🎉

There’s even more happening all holiday season in Downtown Pittsburgh, including small business shopping giveaways, shows, free activities, and more. Get all the details here.