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A riding horse on its own is considered Large in game terms (20 square feet). When it's drawing a cart, what size is it considered to be?

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Carts are Large objects, per the table of sample object sizes on p. 247 of the DMG.

So a horse with a cart is a Large creature pulling a Large object, occupying a 10' wide x 20' long area.

Note that this isn't treated as a single creature, since creatures can squeeze to move through spaces one size smaller than themselves. Objects, including carts, cannot squeeze.

There are no specific rules for how a horse and cart can move (in terms of actions, speed, or limits to turning). D&D 5e generally prefers to leave details like that up to the DM.

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  • \$\begingroup\$ But if it occupies a space of 10 x 20 feet how do you spin it around every direction becouse it's not a square it's harder to make it move in any direction? \$\endgroup\$ – Spellcaster Apr 15 '17 at 19:29
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    \$\begingroup\$ @Spellcaster that's kinda the point, isn't it? You can't rotate a real-life horse & cart in place either. \$\endgroup\$ – Erik Apr 15 '17 at 20:38
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    \$\begingroup\$ @Spellcaster There are no rules for that. Running combat on a grid is itself an optional rule. D&D 5e isn't a tactical miniatures wargame, and by design doesn't provide specific rules for every possible circumstance. \$\endgroup\$ – Marq Apr 16 '17 at 3:33

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