5 of Our Favorite Fall Things to Do Around Philadelphia
At Pearl Properties, we love that luxury living in Philadelphia means more than a beautiful home. It is about being close to everything that makes the city special, from scenic trails and waterfront views to neighborhood festivals, great food, and easy weekend getaways.
With fall officially here, we rounded up five of our favorite ways to enjoy the season around Philadelphia.
1. Bike from Center City to the Wissahickon
One of our favorite ways to enjoy a crisp fall day is to hop on your bike and head from the city to the Wissahickon.
In about 30 minutes, you can trade Center City streets for wooded trails, changing leaves, and beautiful views throughout Wissahickon Valley Park. It is an easy way to enjoy a little nature without going too far from home, and it is completely free.
Our tip: Pack a coffee, grab your bike, and make a morning of it.
Philadelphia, Pennsylvania, USA dawn on the Schuylkill River at Boathouse Row.
2. Catch the Head of the Schuylkill Regatta
October 24 and 25, 2026
Boathouse Row
Fall in Philly would not be complete without a trip to the river. The Head of the Schuylkill Regatta brings rowing races to the Schuylkill River with Boathouse Row as the backdrop.
The event is free to watch and, for Pearl residents in Center City, it is an easy bike ride to the river.
See the Head of the Schuylkill Regatta schedule
3. Spend a Day at Longwood Gardens
October 2 through November 15, 2026
For a classic fall day trip, Longwood Gardens is hard to beat. Autumn brings colorful gardens, seasonal displays, fountains, and special evening experiences.
During October, the Gardens are open from 10am to 6pm Monday, Wednesday, and Thursday, and from 10am to 9pm Friday through Sunday. They are closed Tuesdays.
October also brings special Fountain Fest weekends, including Emerald City Weekend October 16 through 18 and Spellbound Weekend October 23 through 25.
Plan your visit to Longwood Gardens
4. Check Out a Fall Festival
One of the best things about Philadelphia in the fall is that there is always something happening.
On October 3, Evil Genius is celebrating its 15th anniversary with a music filled block party in Fishtown featuring live music and vendors.
Looking for something closer to Rittenhouse? Open Streets West Walnut turns Walnut Street into a car free space for strolling, shopping, dining, and activities. It runs Sundays through October 25 from 10am to 5pm.
And for the foodies, the Philadelphia Street Food Festival takes over Stateside Live on October 24 and 25, featuring more than 30 food trucks and restaurants, live entertainment, and plenty of food to enjoy.
Explore Open Streets West Walnut
Learn more about the Philadelphia Street Food Festival
Jim Thorpe, PA; October 20, 2023; A scenic train in the mountains of Pennsylvania in the fall with colorful leaves
5. Take a Fall Foliage Train Ride to Jim Thorpe
Ready for a little getaway? Head to Jim Thorpe for a day surrounded by mountain views, charming streets, and fall foliage.
The Lehigh Gorge Scenic Railway is a classic way to experience the area during peak autumn colors. Grab a seat on the train, relax, and enjoy the scenery as you travel through the gorge. Then spend some time exploring downtown Jim Thorpe before heading home.
It is the perfect fall day trip when you want to get out of the city without going too far.
Fall Looks Good on Philadelphia
One of our favorite things about living in Philadelphia is how easy it is to experience a little bit of everything. You can start your morning with a bike ride through the Wissahickon, spend the afternoon exploring a neighborhood festival, or take a weekend trip into the mountains, all while having a luxury home in the heart of the city to come back to.
That is the Pearl Properties lifestyle: beautiful spaces, incredible locations, and Philadelphia right outside your door.
Explore Pearl Properties and find your place in Philadelphia