As the days grow longer and the blooms get brighter, May brings a fresh lineup of activities to celebrate the season. From colorful flower shows and food truck rallies to music festivals, this month’s events offer exciting ways to enjoy the arts, culture, and charm of Pennsylvania. Header image credit: PGA of America
Wayne Art Center Plein Air Festival
Watch creativity bloom during the 18th Annual Wayne Art Center Plein Air Festival. Artists set up their easels in scenic landscapes across Delaware County, capturing the essence of spring en plein air. Don’t miss your chance to see art come to life this spring.
When: May 3-9, 2026
Where: Wayne
New Hope PrideFest 2026
Join the celebration of love, pride, and community at New Hope PrideFest 2026. From the vibrant Pride Parade on May 16th featuring the 100-foot Rainbow Equality Flag, to pride bingo and dance parties, the free celebration showcases the town’s creative spirit and welcoming community.
When: May 9–17, 2026
Where: New Hope
108th PGA Championship
Fore! Pennsylvania is teeing up one of the biggest moments in golf when the 2026 PGA Championship comes to the historic Aronimink Golf Club in Newtown Square. One of golf's four major men's championships, this prestigious tournament returns to the Philadelphia region for the first time since 1962. Watch more than 150 of the world's elite golfers compete for one of the sport's most coveted titles, with 200,000 fans expected to soak in every swing. Whether you're a die-hard golf fan or just looking for a bucket-list experience, this is Pennsylvania's can't-miss event of the spring!
When: May 11–17, 2026
Where: Newtown Square
Fine Arts Fiesta
Did you know Fine Arts Fiesta is the oldest running arts festival in Pennsylvania? This year's 70th annual event, “70 Trips Around the Square” is a four-day celebration in downtown Wilkes-Barre featuring an Artists Market along with family-friendly musical performers.
When: May 14–17, 2026
Where: Wilkes-Barre
2026 Upper Pine Creek Trout Tournament
Cast a line and enter this year's ultimate 2026 Upper Pine Creek Trout Tournament in Potter and Tioga Counties. With cash prizes up for grabs, including a $1,000 Grand Prize and special $250 "America's Birthday" prize celebrating the U.S. Semiquincentennial, this family-friendly event is a perfect way to experience the region's scenic streams and small-town charm. Don't forget to register before you fish!
When: May 16-17, 2026
Where: Wellsboro
Derby at the Vineyard
Sip, savor, and celebrate spring during Derby at the Vineyard. This festive weekend at Penns Woods Winery near Delaware features a hunter horse jumping show, live music, wine, local beer and cider, food trucks, and an artisan market—all set against the scenic backdrop of rolling vineyards. Dress in your most stylish derby attire for the chance to win "Best Dressed!"
When: May 16–17, 2026
Where: Chadds Ford
Photo Credit: Kat Kuo
South 9th Street Italian Market Festival
Attend the oldest outdoor market this spring in the heart of the Italian Market in Philadelphia at the iconic South 9th Street Italian Market Festival. This free street festival has merchants lining the streets for seven city blocks and offers an extravaganza for the senses with every ethnic delicacy possible, live entertainment, and fun contests. Don’t miss the iconic grease pole climbing competition where teams climb a 30-foot pole greased with lard for prizes or the halfball tournament that celebrates Philly’s favorite street game.
When: May 16–17, 2026
Where: Philadelphia
Myerstown Carnival
This is the season to get to Myerstown, situated just 40 minutes outside of Hershey, for the second annual Myerstown Carnival. Savor delicious eats from food trucks and local vendors and experience the thrill of carnival rides and games. With live music and entertainment, it’s a new celebration you won’t want to miss. On May 25, be sure to catch their one-night-only firework show to officially kick off the summer.
When: May 20-25, 2026
Where: Myerstown
Greater Pittsburgh Food Truck Festival
Bring your appetite to the Greater Pittsburgh Food Truck Festival! Held at the Hollywood Casino at The Meadows just 30 minutes outside of downtown Pittsburgh, this Memorial Day weekend event features more than 50 food trucks serving up everything from street eats to sweet treats. Enjoy live music, craft beer and wine, and shop from regional artisans and vendors.
When: May 22–24, 2026
Where: Washington
58th Annual Harrisburg Artsfest
Prepare for a celebration of art like no other at the 58th Annual Artsfest in Harrisburg. This exciting festival brings together more than 170 artisans, offering their handcrafted work including ceramics, jewelry, and sculpture. Among the stunning artwork, enjoy live entertainment, a Kidsfest, and food trucks offering a variety of delicious options. Explore the Harrisburg Art District with art museums, galleries, and more than 40 public murals. Come for the art, stay for the fun, and experience Harrisburg's dynamic cultural scene!
When: May 23–25, 2026
Where: Harrisburg
Commonwealth Concert Series
Celebrate America’s 250th where it all began. As the birthplace of the nation, Pennsylvania is at the heart of the Semiquincentennial, and the Commonwealth Concert Series is bringing the celebration to five cities across the state. This free summer tour, that’s now open to out-of-state friends, runs May 23 through June 27, with Grammy-winning artists like Lady A, Nelly, The Avett Brothers, and Third Eye Blind taking the stage in State College, Erie, Hershey, Wilkes-Barre, and Pittsburgh.
More than just a concert, it’s your chance to experience Pennsylvania’s regions, from Hershey’s sweet charm to Pittsburgh’s city energy, all set to a world-class soundtrack. Admission is free, but tickets are required and going fast, with some shows already sold out. Secure your spot now on America250PA.org.
When: Select dates between May 23 to June 27, 2026
Where: State College, Erie, Hershey, Wilkes-Barre, and Pittsburgh
Fish-For-Free Days
Reel in some fun during Fish-For-Free Days. On this special day, anyone can fish on Pennsylvania’s beautiful waterways without a fishing licenses. It’s the perfect chance for residents and visitors alike to experience the joy of fishing, whether you’re a seasoned angler or casting a line for the first time. Grab your gear, cast a line, and make some memories! If you miss this Fish-for-Free Day, don't worry - the second, and final, Fish for Free Day will take place on July 4.
When: May 24, 2026
Where: Statewide
Cook Off & Music Festival
Sink your teeth into award-winning BBQ at the 35th annual Erie’s Wild Rib Cook Off & Music Festival. Nationally acclaimed pitmasters compete for top prizes in ribs and sauce, while local artisans, live music, and family-friendly attractions fill downtown Erie’s Perry Square. Adults can stop by the beer and spirits garden while the kids run wild in the Fun Zone.
When: May 27–30, 2026
Where: Erie
Photo Credit: J. Fusco
Roots Picnic
Rolling Stone calls it “hip-hop’s greatest festival” and you can kick off your summer listening to some of the nation’s top artists at The Roots Picnic Music Festival in Philadelphia. Hosted by The Roots, a legendary hip-hop group native to Philadelphia, each year the festival is equipped with an all-star line-up. This year get a front row spot to see Jay-Z & The Roots, Erykah Badu, Kehlani, Brandy, T.I., Mariah the Scientist, and more!
When: May 30–31, 2026
Where: Philadelphia
Strawberry Festival
Sweeten up your season at the 11th Annual Strawberry Festival at Hollabaugh Bros near Gettysburg. Taste fresh-picked strawberries and homemade desserts, like sundaes, sugar cakes, and muffins, while listening to live music at this free event. Kids and adults alike can hop on a wagon ride around the farm or cool off with a strawberry milkshake.
When: May 30-31, 2026
Where: Biglerville
For more can’t-miss spring events and festivals in Pennsylvania, visit our events calendar.