If it's a vehicle being operated on a commercial basis, then yes, that combination will need a CDL. Commercial vehicles and combinations in excess of 26,000 lbs. Gross Vehicle/Gross Combination Weight Rating require a CDL. For that combination, you would need a Class A CDL (combinations over 26k GCWR with a trailer in excess of 10,000 lbs. GVWR).
If the vehicle is a registered farm vehicle, it does not require a CDL if the following criteria is met:
If the vehicle is a registered recreational vehicle, and is not operated on a for-hire basis, no CDL is required.
Even if the vehicle falls under an exemption from CDL requirements, individual states may impose their own licencing requirements for non-CDL vehicles and combinations with a Gross Weight Rating of more than 26,000 lbs. As I'm not privy to know which state you're operating in, you'll have to inquire with your state's DMV.
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