Starting points. Gresham requests most often begin in Downtown Gresham, Rockwood, Pleasant Valley and Centennial. A street address beats a neighborhood every time. Where a 40-foot vehicle can stop is a narrower question than where you live.
Where groups go. Destinations named for Gresham include Mt. Hood Community College, Gresham Center for the Arts, Main City Park and McMenamins Edgefield (nearby Troutdale). Loading rules vary by venue. Pick a meeting corner up front so nobody is hunting for the bus at the end of the night.
Dates that fill first. Local calendars around Gresham Arts Festival, Mt. Hood Jazz Festival (historical), Gresham Farmers Market and Edgefield concerts concentrate demand into a handful of weekends. Check the current schedule with the organiser — this is not a live calendar.
Popular runs. Gresham to Portland nightlife (20 min); McMenamins Edgefield concert shuttle (10 min); Gresham to Mt. Hood ski shuttle (1 hr). Stop order and end time matter more than distance. Send both.
Beyond Gresham. Trips that continue into Albany, Beaverton, Bend or Corvallis are quoted as one itinerary. The Oregon guide covers statewide staging and long-distance planning.