• 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…

  • 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…

  • 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…

  • Pgh Book Fest

    Pgh Book Fest is a free, all-ages celebration of books, storytelling, and Pittsburgh’s literary community. Held at Carnegie Library of Pittsburgh’s Main branch in Oakland, the festival includes author talks, poetry readings, workshops, children’s activities, local booksellers, vendors, and more. The 2026 festival takes place Saturday, May 30 from 10 a.m. to 5 p.m.

  • Party in the Park Carnegie

    Join Carnegie Borough at Carnegie Park on Saturday, May 30 for the annual Party in the Park from noon to 10 PM. The all-day free event features a classic car cruise, food trucks, live bands, kids activities, fireworks, and much more. A beloved community celebration for the whole family. Located at 1099 Forsythe Road, Carnegie,…

    Free
  • 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…

  • 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…