• Free Kid May at Pennsylvania Trolley Museum

    Kids visit for free in May 2026! Ride a real vintage trolley and explore interactive exhibits at this hands-on museum—fun, unique, and perfect for families of all ages. May Hours are Thursday - Sunday, as well as Monday, May 25th for Memorial Day. 10:00 AM - 4:00 PM 💡 Planning to go? Read our full review…

  • Greensburg Night Market II

    Greensburg Night Market II returns to South Pennsylvania Avenue in downtown Greensburg, featuring 4+ city blocks of local vendors, artisans, and shopping. The market has grown since 2019 to host 500+ different vendors over its history. Free to attend.

    Free
  • Pittsburgh Riverlife Chalk Festival

    Riverlife Chalk Fest brings Pittsburgh’s riverfront to life with colorful chalk murals, hands-on art, live music, food, and family-friendly fun along the North Shore. Professional artists transform the pavement around Isabella Street, Allegheny Landing, and the Three Rivers Heritage Trail into a giant outdoor art gallery, and visitors can watch the murals come together, meet…

  • Pittsburgh Pirates Home Game

    PNC Park 115 Federal St, Pittsburgh, PA, United States

    Pittsburgh Pirates Home Game at PNC Park. Cheer on the Pirates at a home game at PNC Park! Enjoy a family-friendly atmosphere, ballpark snacks, and one of the best skyline views in baseball. Pirates Home Games at PNC Park Date Time Opponent Promotion Fri, Apr 3 4:12 PM Orioles Opening Weekend Sat, Apr 4 4:05…

  • Free Kid May at Pennsylvania Trolley Museum

    Kids visit for free in May 2026! Ride a real vintage trolley and explore interactive exhibits at this hands-on museum—fun, unique, and perfect for families of all ages. May Hours are Thursday - Sunday, as well as Monday, May 25th for Memorial Day. 10:00 AM - 4:00 PM 💡 Planning to go? Read our full review…

  • Grease: Outdoor Movie & Live Choir Sing-Along

    Frick Pittsburgh hosts a screening of Grease accompanied by a live choir sing-along at 8:45 PM on May 29. Bring your blankets and lawn chairs for this magical outdoor movie experience where you can belt out your favorite songs with live musical accompaniment. Tickets range from approximately $10 to $20. Gates open earlier for picnicking…

    $10
  • The Lights Festival

    The Lights Fest is a sky lantern festival coming to the Pittsburgh area at Lawrence County Fairgrounds in New Castle. Families can enjoy live music, food trucks, entertainment, and time to decorate lanterns before the evening lantern release lights up the sky. Adult tickets include a lantern and marker; kids ages 4–12 need a kid…

  • Free Family Fishing at Carnegie Lake

    Highland Park Reservoir Dr, Pittsburgh, PA, United States

    Fishburgh Outdoors, a Pittsburgh 501(c)(3) nonprofit, hosts free family fishing events at Carnegie Lake (Lake Carnegie), Highland Park, Pittsburgh PA. Contact info@fishburgh.com or check fishburgh.com for the confirmed 2026 event schedule.

    Free
  • Sunset Music Festival

    Southpointe Town Center 1900 Main St, Canonsburg, PA, United States

    Annual outdoor community music festival at Southpointe Town Center, 1900 Main Street, Canonsburg PA 15317, supporting Best Buddies (an organization serving people with intellectual and developmental disabilities). Live music performances, DJ sets, bounce houses, games, raffles, and giveaways. Family-friendly. Food and drinks available for purchase. Start time TBD — check sunsetmusicfest.org for the 2026 schedule.

  • Strawberry Festival at Parkwood Church

    Parkwood Church 4289 Mt Royal Blvd, Allison Park, PA, United States

    Parkwood Church in Allison Park hosts its Strawberry Fest 2026 on May 30, celebrating the season with strawberry-themed foods, activities, and community fun. This beloved annual event draws nearly 200 attendees who come to enjoy strawberry shortcake, local vendors, and family-friendly activities. A sweet way to welcome summer. Located at 4289 Mount Royal Blvd, Allison…