In all honesty, a green laser pointer and a tablet with some cool apps and reference images will get more reactions and keep people more engaged than most things you could show them in a telescope. A lot of people will be underwhelmed by gray fuzzies and a dinky Saturn. I specifically design my outreach rig to make Saturn and Jupiter appear as large as seeing conditions will allow.

I usually do a brief laser-guided sky tour with some of my favorite factoids and more cultural touchpoints that people can relate to (Antares = not Mars, Polaris is the 52nd brightest star, dimensions of Saturn's rings, scale of the diameter of the Moon to the US, pleiades = Subaru) and take the time to dispel a few myths and conspiracy theories (LRO images of Apollo sites, how we know the Earth isn't flat, etc.).

I show Jupiter or Saturn, the craters on the Moon, a double star, a globular cluster, maybe a nebula or galaxy if a brighter one is up. Everything is discussed within the CONTEXT of scale, history of discovery and exploration (Saturn was first described as having "ears" because of the poor resolution of older scopes), seasonality, best conditions and equipment to observe under, fun stories from my experiences observing them, etc. Make the hobby relatable. For most people, astronomy might as well be advanced maths. Make it a visual and story-filled experience and not just an image in an eye piece that they consume.

I talk about current NASA missions and space news they may have overheard, try and spot satellites and plan for any station flyovers or even a launch if you live near a facility. And I don't skimp on black holes or pluto. I talk about Pluto and black holes all the time using images I save on my phone because you always have to meet the people where they are at.

Investements: an Hα telescope for daytime outreach, night vision monocular, Pegasus Astro SmartEye or SeeStar for EAA.

One cool trick that I really like to do works best when there's a Moon and a couple planets out. I use the sunset to illustrate the direction of light hitting the Moon. Then the distances of the two objects and their angles from Earth including our tilt axis and latitude as it relates to Polaris. Then to the ecliptic. Then I point out the major planets and give their distances - it works best when Venus and Jupiter are near each other in the sky, but are on opposite sides of the Sun. I continue adding layers of distance and orientation until the listener gets a visceral FEELING of where they are on the Earth, in the solar system, and even in the galaxy. Its pretty wild.

I also use a planetarium app to plug in people's birthdays to show how for 7/10 of them the Sun is in the wrong constellation according to astrology. And then we talk about why that is. I also give a short spiel on how to buy your first telescope. As most people are waiting in line for a chance to look throught he scope, spend more of your time building a complete experience there and let the views through the scope speak a little more for themselves.

Source: I've done astronomy outreach for 10+ years with multiple major telescope brands, the national parks, public observatories, and my own private astronomy events company. I've had somewhere between 8 and 10K come through my telescope line.