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This Season’s Fun Holiday Events Near Philadelphia


If you live on the East Coast, you know that the winters there are no joke. However, despite the snow and freezing temperatures, there are countless holiday events throughout Pennsylvania for the whole family. Whether it’s visiting a Christmas village or attending your favorite holiday market, there’s sure to be something for everyone to enjoy. So if you and your family are looking for holiday events near Philadelphia, look no further. Here’s a list of this winter’s top holiday happenings.

This Winter’s Top Holiday Events Near Philadelphia

  • Christmas Village in Philadelphia
  • Made in Philadelphia Market
  • The Philly Pops
  • Santa’s Express
  • SantaFest
  • Holiday History Stroll

Christmas Village in Philadelphia

One of the most popular holiday events in Philadelphia, running for its 14th season this year, is the Christmas Village. This event transforms LOVE Park and City Hall and turns the scene into an authentic German Christmas market. 

The Christmas Village in Philadelphia is running from Thanksgiving through Christmas Eve (November 25th- December 24th, 2021). So if you are looking for holiday events in the area, don’t miss out on the Christmas Village. With over 80 vendors, there’s something at the event for the whole family. 

This Season’s Fun Holiday Events Near Philadelphia

Made in Philadelphia Market

Along with the Christmas Village, the Made in Philadelphia Holiday Market will also be going on during this time. From November 25th until January 1st, across the street from the Christmas Village, you’ll find one of Philadelphia’s favorite outdoor family events. 

So, if you’re looking for an activity that you can bring the whole family to, check out the Christmas Village in Philadelphia as well as the Made in Philadelphia Market. 

The Philly POPS: Spectacular Sounds of the Season

From December 4th through December 18th, the Philly POPS are back for another holiday celebration. If you didn’t know, the Philly POPS is the largest standalone pops orchestra in the United States. This talented group recognizes and celebrates American traditions through the heritage of song. That said, if you attend this famous Philly event, you’ll hear classic Christmas songs such as: 

  • Silver Bells
  • Angels We Have Heard on High
  • Winter Wonderland
  • I’ll Be Home For Christmas
  • Joy to the World
  • O Holy Night

Santa’s Express

From November 20th through December 19th, Santa’s Express will be visiting the West Chester area. For this event, Santa will be meeting passengers at Market Street Station and taking them along for a train ride to Glen Mills and back. The journey with Santa lasts 75 minutes and takes you through the Chester Creek Valley. 

You can purchase tickets for this event online at the following costs:

  • Adults – $30
  • Children – $25
  • Toddlers – $10
  • Infants under nine months ride free


For this unique annual event in West Chester, on December 11th, Santa Claus will fly into the American Helicopter Museum and Education Center in a helicopter at 11 a.m. Here, he will sit down with the children to go over their Christmas wish lists. So, make sure to bring your cameras and Christmas wish lists to SantaFest this year.

For this event, kids age 12 and under are free. Children 13 and over are $10, and so are adults. If you are a museum member, you may attend for free. 

Holiday History Stroll

History lovers won’t want to miss this Christmas event— the Holiday History Stroll in West Chester. This event is brought to you by the historians and educators at Chester County History Center and puts you in the holiday spirit with a walking tour that lasts an hour and a half. 

Here, your tour guides will lead you to West Chester’s oldest churches and other cultural sites, teaching you about what “Christmas” meant to the people of West Chester back in the 1700s to the early 1900s. The ticket price includes a festive libation toast at a local restaurant. 

Common Winter Activities Near Philadelphia

There are tons of winter activities for you and your family to discover throughout the Philadelphia area. Whether it’s going for a family hike, shopping for Christmas gifts, or ice skating at a local rink, there are activities for kids of all ages to enjoy. So let’s check out some of the most common winter activities near Philadelphia. 

  • Going for a Family Hike
  • Skiing or Tubing
  • Outdoor Ice Skating Rink

This Season’s Fun Holiday Events Near Philadelphia

Going for a Family Hike

If you’re looking for an excuse to get moving, bundle up and take the family for a hike. With that, if you need inspiration for hiking trails near Chester County, check out this helpful hiking trail guide. Luckily, most trails allow pets and are extremely beautiful in the winter. 

Skiing or Tubing

If you’re looking to plan a winter retreat, consider booking a trip to Bear Creek Mountain Resort. This resort is just a short drive from Philadelphia, New York, Washington D.C., and Baltimore, so it’s the perfect getaway no matter where you’re located. This Season’s Fun Holiday Events Near Philadelphia

Outdoor Ice Skating Rink

One of Philadelphia’s favorite winter traditions is Blue Cross RiverRink Winterfest. This event runs from December 24th through January 2nd, with varying hours on New Year’s Eve and Christmas Day. While general admission is free, tickets for the outdoor ice skating are based on a timed entry system and can be pre-ordered online. The skating rink is a great place to gather for family fun in the winter. 

Are You New to the Chester County Area?

Philadelphia is filled with fun seasonal activities that the whole family can enjoy during the winter months. In addition, the bustling neighboring cities bring in people from all parts of the world to unite them with warm holiday traditions. If you live in Chester County, you know plenty of holiday events near Philadelphia coming up. However, those who aren’t familiar with the area may not be aware of the activities and events this winter. 

Are you new to the area and looking for a rental home? If so, Bay Property Management Group can help you find the perfect rental property for you and your family. Our dedicated team of professionals works with tenants to help find the best rental to suit their needs. So, if you are searching for a place to live in the Chester County area, contact our full-service team today