PHILADELPHIA, PA - Think you know Philly? Think again! This week, the city is offering a surprising mix of events that will delight and entertain. Sip on a "Hamilton" cocktail, indulge in vegan delights, meet Eagles legends, or find your zen under the moonlight. Discover a new side of Philadelphia with our curated event guide.

The Ultimate Guide to What’s Happening in the Philadelphia Region This Weekend and Next Week

As September wraps up and the crisp October air rolls in, the Greater Philadelphia region is packing its calendar with massive block parties, retro concerts, and philanthropic celebrations. Whether you are looking to run a 5K for land preservation, sing along to 1990s hip-hop anthems, or drink craft beer at a neighborhood street fair, there is an event for every speed.

Here is your complete guide to the best regional events happening this weekend and into next week.

This Weekend: September 25 – 27

Friday, September 25: Dolly Parton Day Celebrations

Kick off your weekend by celebrating the Queen of Country. The inaugural citywide holiday is taking over independent neighborhood venues, turning happy hours into high-energy tributes. If you are scouting spots to catch a drag showcase at Stir Lounge in Rittenhouse or sing along to "9 to 5" at Center City's iconic Dirty Franks, check out our complete guide on where to celebrate Dolly Parton Day in Philly. Beyond the rhinestones and cocktails, participating locations are raising funds directly for the Philadelphia Imagination Library to help eradicate early childhood illiteracy.

Saturday, September 26: I Love the 90's Tour at Parx Casino

If you are craving pure nostalgia, head just outside the city to Bensalem. The Xcite Center at Parx Casino is kicking off its fall retro concert series with the massive i love the 90's tour starting at 7:30 PM. The dance party features performances by Vanilla Ice, Fab Morvan of Milli Vanilli, Freedom Williams of C+C Music Factory, and Young MC. To explore the complete autumn lineup of rock and R&B throwbacks, read more on how 1990s nostalgia takes over Parx Casino’s Xcite Center this fall.

Sunday, September 27: 19th Annual Dogfish Dash

For a Sunday morning coastal road trip, head down to Milton, Delaware, for a beloved craft beer tradition. The Dogfish Head Milton Brewery is hosting its 19th Annual Dogfish Dash beginning at 9:00 AM. The morning features a signature 5(ish)K run, a 1.5-mile pet-friendly walk, and the fan-favorite recycled costume contest. All proceeds from the day directly benefit the Sussex County Land Trust to support local conservation efforts.

Next Week: October 1 – 3

Thursday, October 1: A Taste of Britain’s 35th Anniversary Begins

As the calendar flips to October, head out to the Main Line to celebrate a culinary milestone. A Taste of Britain, the beloved tea room in the Eagle Village Shops in Wayne, is launching a month-long celebration for its 35th anniversary. Guests can order a special $35 three-course prix fixe menu featuring warm homemade scones, signature toasties, and orange posset, with proceeds donated to the Wayne Senior Center. Weekday visitors can also take advantage of rolled-back $35 Full Afternoon Tea pricing Monday through Thursday.

Saturday, October 3: 14th Annual Roxtoberfest

Get ready for one of the largest fall celebrations in the city. From 12:00 PM to 6:00 PM, the 14th Annual Roxtoberfest brings fall fun and craft beer to Ridge Avenue between Lyceum and Leverington Avenues. The free street festival features over 100 artisan vendors, food trucks like Deke's BBQ and Federal Donuts, and seasonal pours from New Ridge Brewing Company.

Entertainment includes the PAWrade Pet Costume Contest, stein-holding competitions, and historical cemetery tours, providing a modern spin on the historic roots of Philadelphia's Oktoberfest tradition. For a broader look at tastings, taproom releases, and events throughout the season, check out our guide to Oktoberfest 2026 in Philadelphia: Where to Celebrate, Eat and Drink This Fall.