We all feel the cold crisp in the air, Christmas music is already playing in stores, and it is pitch black dark outside by 6:00 pm. I know Halloween is barely in its coffin and thanksgiving break is not here yet (believe me, I am aware I am counting the days). I have already started planning some of my favorite yearly holiday activities in the city and today I am going to share them with you. As a Philadelphia-born girly (Go birds) I have been doing some of these things since before I can even remember so trust me I am a reliable source. Many of those who live here know these things but to the people who are new or unfamiliar to Philly or just planning to visit one day, these are some things you must try to do while you are down here.
1. Winter fest at Penns Landing
Visit Independence Blue Cross River Rink November 28th, 2025 through March 1, 2026, any day of the week (including holidays!) for a full holiday experience. Sit by a fire pit or relax in a heated cabin. Enjoy the variety of delicious food, hot drinks, and snacks available for purchase while viewing the signature holiday tree. The main event at winter fest is ice skating on the NHL-sized rink with a beautiful view of the Delaware river right across the way. I visit the riverink several times during the winter. It is my favorite activity.
2. The Macy’s Holiday light show
Despite the recent closure of the iconic center city Macy’s location, the Wanamaker Light Show (formerly the Macy’s Light Show) carries on. For over 50 years Philadelphians have made trips over to the Wanamaker Building (which is what eventually became the Macy’s) to see the show. Hundreds of twinkling lights and festive music come together with visuals of dancing snowflakes, snowmen, and reindeer to create the iconic show. The light show is free to attend and runs every hour on the hour during hours of operations. Enjoy it now while you can as the light show will officially go on hiatus for the 2026 and 2027 holiday seasons because of construction.
3. The Holiday Village at Peddler’s Village
Take a walk through the enchanted village while exploring 65 specialty shops and boutiques. During your time here you can choose to enjoy either fine or casual dining experiences. Starting on November 14 the holiday magic begins. All season long enjoy family-friendly events, a Santa parade, photos with Santa Claus, and enchanting holiday tunes. If you bring along any little ones be sure to take a spin on the 1920s carousel (one of the true gems of the village) and play around in the arcade. If you are interested, visit the Peddlers Village website to find the dates of the upcoming holiday events.
4. Dilworth Park
Visit the Rothman Orthopaedics Ice Rink at Dilworth Park from November 14, 2025 to February 22, 2026 to see one of the most popular wintertime locations in all of Philadelphia. My advice? Book your tickets in advance as it can get really busy because the in-person sales are pretty limited. The skate sessions are 90 minutes long with a 30 minute break in between each session. If you own a pair of skates make sure to bring them as you will then only need to pay for your admission and you can save a couple of bucks. If you need a place to store your things while you are out on the rink, lockers are available to rent on-site if needed. I highly recommend this activity if you get the chance to visit!
5. Franklin Square
Last but certainly not least, historical Franklin Square also gets a holiday make-over and it is stunning. Winter in Franklin Square is a true wonderland. As soon as the sun sets, the magic begins. Enjoy all-age attractions and experience dazzling lights during the free Electrical Spectacle Light Show. Explore all the park’s winter activities such as the Parx Liberty Carousel and the Chilly Philly Mini Golf course. Franklin Square hosts a ton of special holiday events that you do not want to miss. And, do not forget to relax and enjoy treats and sips while sitting by a cozy fire pit while you are in the village.
The holidays are truly magical in Philadelphia and gems like these are what gives the city its winter charm. If you have the opportunity to visit any of these locations do not pass on it. Each offers a memorable experience that you will not soon forget. You can enjoy the festivities with anyone, your friends, family, or partner; there is something here for everyone. So, grab your winter gear and head downtown, the Philly holidays await. I know I will be there.