From pumpkin picking to wine tastings, here are the best things to do this fall in Philadelphia. 
Auburn Vineyards
October is Pennsylvania Wine Month, so stopping by a vineyard is a must. A short 45-minute drive from Philly is one of our favorites: Auburn Vineyards. Spend an afternoon or evening at The Enoteca, a European-style vineyard wine bar that offers wine, cheeses, woodfired pizza and gelato on a gorgeous, Wisteria-covered patio. While sipping on one of Auburn Vineyard’s signature wines, guests can also enjoy live performances from local musicians every Saturday. 117 Sharptown Auburn Road, Pilesgrove, N.J., auburnroadvineyards.com
FallFest at Shady Brook Farms
Leave behind the city for a day at Shady Brook Farm’s FallFest. Visitors can find apple and pumpkin picking, wagon rides, a five-acre corn maze, sunflower fields, bonfires, live music on the weekends and more. After a day of fun on the farm, reserve a campfire for toasty s’mores. For a festive treat, visit the farm at night for their bright and colorful Halloween display, Eerie Illuminations. Opens September 9, 931 Stony Hill Road, Yardley, shadybrookfarm.com
Halloween Nights at Eastern State Penitentiary
Nothing quite says spooky like a Halloween-themed, 200-year-old penitentiary. This 10-acre prison may no longer hold America’s lawbreakers, but their Halloween Nights festival, full of fangs, gargoyles and skeletons, is not to be missed. From September 22 to November 11, venture through five haunted houses, wander around immersive kaleidoscopic walkthroughs or go on a self-guided audio tour featuring the voices of real incarcerated people at Eastern State. If you need to take a break from your spooky surroundings, the attraction also offers drinks at The Speakeasy at Al Capone’s Cell, live music at Junkyard Jam and more. 2027 Fairmount Ave., easternstate.org
Head of the Schuylkill Regatta
Established in 1970, the Head of the Schuylkill Regatta is one of the largest rowing competitions in the world. The Regatta welcomes over 90,000 participants, including college and high school crews, master rowers, elite rowers and world champions. More than 30,000 spectators attend the two-day festival every year, and this year, the rowers will once again be racing down the Schuylkill on October 28 and 29 for the regatta’s 53rd competition. hosr.org
The Philadelphia Orchestra’s Opening Night Celebration
Starting another year of music with a bang, The Philadelphia Orchestra will take to the Kimmel Center for the Performing Arts stage on September 28. To inaugurate the 2023-24 season, the Orchestra welcomes Canadian Conductor Yannick Nézet-Séguin and acclaimed cellist Yo-Yo Ma to play Shostakovich’s “Cello Concerto No. 1,” Higdon’s Fanfare Ritmico and Rachmaninoff’s “Symphonic Dances.” For those wishing to elevate their musical night, a benefactor package will also open the evening with a festive pre-concert reception and conclude with an elegant gala dinner. 300 S. Broad St., philorch.org
Photography by: Gerda/Unsplash
