• Neighborhood Flea – Mother’s Day Edition

    Southside Works 424 S 27th St Suite 300, Pittsburgh, PA, United States

    The Neighborhood Flea hosts its Mother's Day Edition at SouthSide Works on May 10 from 10 AM to 3 PM. Browse curated vintage items, handmade goods, and unique gifts perfect for Mother's Day. Free admission, located at SouthSide Works, Pittsburgh. A wonderful way to find a special gift for Mom while supporting local vendors and…

    Free
  • Mother’s Day Dinner Cruise – Gateway Clipper Fleet

    Gateway Clipper 350 W Station Square Dr, Pittsburgh, PA, United States

    Celebrate Mother's Day with a scenic dinner cruise on Pittsburgh's three rivers aboard the Gateway Clipper Fleet. Enjoy gorgeous views of the Pittsburgh skyline while dining in style. Multiple cruise times are available on Mother's Day weekend. Visit gatewayclipper.com for current pricing and to make reservations — these popular cruises sell out quickly.

  • Sensory Friendly Afternoon at Children’s Museum

    Children's Museum of Pittsburgh 10 Children's Way, Allegheny Square, Pittsburgh, PA, United States

    The Children's Museum of Pittsburgh hosts Sensory Friendly Afternoons on the second Tuesday of every month from 1:00 to 5:00 PM. Lights and sounds throughout the museum are adjusted, and designated Quiet Areas provide spaces for breaks. Sensory Kits with noise-canceling headphones, sunglasses, fidgets, and other tools are available. Regular admission: Adults $19, Children 2-18…

  • Millvale Music Festival

    Two-day festival (#MMF26, May 15–16) featuring 350+ musical acts on 31 stages plus 60 visual artists, spoken word performers, comedians, and food trucks, all within a walkable 0.6-mile stretch of Millvale's unique venues. One of Pittsburgh's premier community music festivals. Free to attend.

  • Bark and Brunch

    Hazelwood Green 4501 Lytle St, Pittsburgh, PA, United States

    Bark and Brunch at Hazelwood Green on May 16 from 11 AM to 1 PM is a dog-friendly outdoor brunch event where four-legged family members are welcome. Enjoy brunch food, beverages, and community gathering in Pittsburgh's growing Hazelwood Green development. A perfect outing for dog-loving families on a spring Saturday morning.

    Free
  • Pittsburgh Youth Symphony Orchestra in Concert – Spring 2026

    Heinz Hall 600 Penn Ave, Pittsburgh, PA, United States

    The Pittsburgh Youth Symphony Orchestra presents their Spring 2026 concert at Heinz Hall on May 17 at 7:30 PM. This exceptional ensemble of young musicians from across the Pittsburgh region showcases the extraordinary talent being developed in our local music programs. An inspiring evening of classical music suitable for the whole family. Visit radworkshere.org or…

  • 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…

  • 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
  • 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.