• 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…

  • 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…

  • Family Farm Tour at The Springhouse

    A Grass to Glass experience at Spring House Market, 1531 Route 136, Washington PA 15301. Tour a real working dairy farm, get up close with the dairy herd, and hand milk a cow. Tickets required; purchase at springhousemarket.com.

  • Opening Day North Boundary Waterpark

    North Boundary Waterpark 1171 N Boundary Rd, Cranberry Twp, PA, United States

    North Boundary Waterpark in Cranberry Township opens for the 2026 season on May 23. The waterpark features slides, a lazy river, and pools suitable for all ages. Mark your calendar and kick off the summer with an opening-day visit to one of Butler County's most popular family destinations. Located at 450 North Boundary Park Drive,…

  • 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…

  • Michael’s Kids Club: Free Craft

    Free weekly in-store kids craft workshop at Michaels. All supplies included; kids take home their completed project. Check michaels.com/events to register and confirm the specific project at your local store.

    Free
  • First Roll at Schenley Park Roller Rink

    Schenley Park Roller Rink 10341 Overlook Dr, Pittsburgh, PA, United States

    CitiParks opens the outdoor Schenley Park Skating Rink for the season with First Roll. Morning session 10 AM–noon; evening session 5:00–8:30 PM. Bring your own quad or inline skates (rentals $3 extra). Tickets online only at citiparksschenleyrink.fearticket.com: Adults $5, Youth (under 15) $3, Seniors/Veterans $4. Sessions limited to 200 patrons. Weather permitting. 2026 opening date…

    $5
  • Mega Reptile Expo

    Monroeville Convention Center 209 Mall Boulevard, Monroeville , PA, United States

    Two-day Western PA reptile and exotic pet expo at the Monroeville Convention Center, 209 Mall Plaza Blvd, Monroeville. Hundreds of reptiles, amphibians, invertebrates, small mammals, feeders, supplies, custom enclosures, photo ops, contests, and giveaways. 3,000 to 5,000 attendees expected. Tickets on Eventbrite. VIP entry at 9 AM; General Admission 10 AM–4 PM.