• Half Price Games on Wednesdays at Zone 28

    Zone 28 2525 Freeport Rd, Pittsburgh, PA, United States

    Get ready for unbeatable fun! All Video, Ticket, and Prize Games 1/2 Price All Day Wednesday! Maximize your gaming experience and make every moment count-more fun, more excitement, and more chances to win! Don't miss out on this incredible opportunity to enjoy your favorite games at an unbeatable price.

  • Roller Skate in Market Square

    Market Square 23 Market Place, Forbes Avenue and Market Place, Pittsburgh, PA, United States

    Looking for fun things to do in Downtown Pittsburgh? Roller skate in Market Square and enjoy one of the newest attractions in the city. The outdoor roller skating rink in Market Square brings music, lights, and retro fun to downtown Pittsburgh all summer long. Whether you’re planning a family outing, date night, or weekend adventure,…

  • 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…

  • Roller Skate in Market Square

    Market Square 23 Market Place, Forbes Avenue and Market Place, Pittsburgh, PA, United States

    Looking for fun things to do in Downtown Pittsburgh? Roller skate in Market Square and enjoy one of the newest attractions in the city. The outdoor roller skating rink in Market Square brings music, lights, and retro fun to downtown Pittsburgh all summer long. Whether you’re planning a family outing, date night, or weekend adventure,…

  • Main Street Farmers Market, Washington PA

    The Main Street Farmers Market in downtown Washington PA operates every Thursday afternoon from mid-May through late October, 3:00–6:00 PM, at 139 S Main St, Washington PA 15301. Features fresh produce, baked goods, honey, meat, dairy, flowers, and artisan goods. Free to attend.

    Free
  • 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…

  • Roller Skate in Market Square

    Market Square 23 Market Place, Forbes Avenue and Market Place, Pittsburgh, PA, United States

    Looking for fun things to do in Downtown Pittsburgh? Roller skate in Market Square and enjoy one of the newest attractions in the city. The outdoor roller skating rink in Market Square brings music, lights, and retro fun to downtown Pittsburgh all summer long. Whether you’re planning a family outing, date night, or weekend adventure,…

  • New Kensington Fridays on Fifth

    Monthly outdoor community event on Fifth Avenue between 9th and 11th Streets in downtown New Kensington. Features food trucks, live music, and downtown shops open late. The May 22 event is the second of the 2026 season, running April through October on the 4th Friday of each month.

  • Greater Pittsburgh Food Festival

    Hollywood Casino 210 Racetrack Rd, Washington, PA, United States

    The Greater Pittsburgh Food Truck Festival runs May 22–24 at Hollywood Casino at the Meadows, 210 Racetrack Rd, Washington PA 15301. Dozens of regional food trucks, live music, craft beer and wine, artisan vendors, and a kids area. Free admission; optional sampler ticket packages available. Hours: Fri 5–9 PM, Sat 12–11 PM, Sun 11 AM–7…