Can you paint over a cast iron stand?

People do paint them. Cast iron takes modern metal paints well as long as the surface is prepared. You have to remove any loose rust and flaking old paint first. A wire brush works best for this. Apply a good metal primer before the top coat to stop moisture getting back into the iron.

My hallway is quite narrow and gets a lot of traffic from the kids, so what shape of stick stand works best without getting in the way?

A flat-backed wooden stand is usually the most practical choice for a tight space. They sit flush against the skirting board and keep the footprint shallow. Cast iron corner stands are another good option. They tuck away out of the main traffic route while still holding plenty of umbrellas.

Do original drip trays have drainage holes?

No, they were designed to hold the water. The whole point was keeping puddles off the floorboards. If you find a tray with holes, it has rusted through. You empty a good tray by lifting it out and pouring the water away.

We just found a wooden stand that has a broken bottom tray, is there any way to replace that part or do we just use it without one?

Using a stand without a tray works fine if you only store dry walking sticks. It becomes a problem if you want to put wet umbrellas in it. You can buy modern metal or plastic liners that fit into the base gap. Some people just find a suitable ceramic trough or roasting tin that drops into the space. It does the job well.

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Gothic Stick Stands

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Found in hallways from the mid-nineteenth century onwards, an antique stick stand is a specialised piece of domestic furniture designed to hold walking canes, umbrellas, and riding crops upright while catching drips in a base tray.