Let me try to address the question even though my oldest car is a 1918, outside the brass era and not eligible for HCCA *national* tours.
I belong to HCCA national as required to participate in three separate HCCA Regional Groups (RG)/Affiliated Registries. A key point is that *regional* HCCA activities often allow post-brass but still pre-WW2 vehicles, sometimes in limited numbers so as not to overwhelm the brass car drivers' need for slower tours. For each event, need for a trailer depends on the capabilities and limitations of your car, and locations of yourself and the start/end points of the event. There are also separate tours limited to one-cyl, 2-cyl, and smaller 4-cyl cars. It's a smorgasbord!
* Bay Area Horseless Carriage Club (BAHCC), a RG, was founded in 1950 and is based in my local area. It is the type of club I grew up with 60 years ago: monthly meetings (some now on Zoom), annual holiday party, July 4 parade with following BBQ at a member's home, monthly half-day hands-on tech sessions at a member's home March-November, monthly one-day tours in the local area March thru November, including a day-after-Thanksgiving Pilgrim's Picnic in which we bring our own TG leftovers plus desserts to share (if inclement weather, we meet at a member's collection).
* South Bay Vintage Touring Club, a RG better known as Nickel Age Touring Club (we had to drop 'nickel' as already taken when signing on with HCCA as national org), which does one annual 3-4-day tour (we used to do two tours per year, but we are suffering from the Aging of the Force). Some are nearby, some require trailering.
* Nickel Era Touring Registry, an "Affiliated Registry" of HCCA, accepts 1932-and-earlier vehicles and has one annual 5-6-day tour in widely dispersed areas (Utah, Idaho, Washington, various locations inside California), and definitely requires trailering. Our superb 2023 tour in SW Utah had about 34 cars from 1912 thru 1932.