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What license you need depends on a number of factors, namely, the vehicle's use, the Gross Combined Weight Rating of the tow vehicle and of the trailer, and the Gross Combined Weight Rating of the two.

For usage, is the vehicle for a business or commercial venture? If so, it's regulated as a commercial vehicle. Private use, there are two possibly applicable exemptions for CDL requirements here -

Recreational Vehicles - when operated for not-for-hire, personal use, these are exempt from requiring a CDL. Now, on a for hire basis, such as hired drivers, or transporters, then they're treated the same as any other commercial vehicle.

Farm vehicles - when registered as such, when operated exclusively for the purposes of that farm (no third party for hire usage), operated within a 150 road/100 air mile radius of the farm, and operated by the farmer, immediate family members of the farmer, or direct (W2/W4, not 1099) employees of the farmer.

Non-commercial vehicles which don't fall under those exemptions can be a bit of a grey area, as many states put commercial plates on pickup trucks used for private use.

So, if it does fall under the criteria of a commercial use vehicle, the length of the trailer has nothing to do with the license required - it's weight.

So now we get into Gross Vehicle Weight Rating. This is the maximum loaded weight the vehicle is rated to run at - a 33,000 lb. GVW vehicle might only weigh 16,000 lbs. empty, but it's treated as a 33,000 lb. vehicle at all times.

Gross Combined Weight Rating is the combined weight rating of all portions of the combination - so, for example, a truck with a 10,000 lb. Gross Vehicle Weight Rating with a trailer which has a 16,000 lb. GVWR comes to a total Gross Combined Weight Rating of 26,000 lbs.

So.. there are three classes of CDL. The 'lowest' being Class C. Class C covers single vehicles with a Gross Vehicle Weight Rating of up to 26,000 lbs., and is used for instances where such vehicles - which normally don't require a CDL - would, such as any vehicle hauling a quantity of hazardous material which requires placards to be displayed under CFR49 regulations, or a commercial or school bus designed to transport more than 15 people (including the driver). In addition to the power unit, a trailer with a Gross Vehicle Weight Rating of up to 10,000 lbs. may be towed without requiring the license to be upgraded.

A Class B CDL is required for any non-exempt single vehicle with a Gross Vehicle Weight Rating of 26,001 lbs. or more. Additionally, a trailer with a Gross Vehicle Weight Rating of up to 10,000 lbs. may be towed without requiring an upgraded license.

A Class A CDL is required for any non-exempt combination where the Gross Combined Weight Rating of the trailer is 10,001 lbs. or more.

These laws are a bit screwy, so let's give it a breakdown...

Single vehicle:

Single vehicle with a GVWR of 0 - 26,000 lbs. = no CDL required unless the conditions for a Class C CDL exist

Single vehicle with a GVWR of 26,001 or more lbs. = Class B CDL is not in an exempt category

Combination vehicles:

Tow unit with GVW of 26,000 lbs. or less and trail unit with GVW of 10,000 lbs. or less = No CDL required unless the conditions for the requirement of a Class C CDL apply.

Tow unit with GVW of under 26,000 lbs. or less and trail unit with a GVW of 10,001 lbs. or more but when the Gross Combined Weight Rating is still under 26,000 lbs. = No CDL required unless the conditions for the requirement of a Class C CDL apply.

Tow unit with a GVW of under 26,000 lbs. and a trail unit of 10,001 lbs. or more for a Gross Combined Weight Rating of 26,001 lbs. or more = Class A CDL required if the vehicle is of a non-exempt category.

Tow unit with a GVW of 26,001 lbs. or more and a trail unit with a GVW of 10,000 lbs. or less = Class B CDL required if the vehicle is of a non-exempt category.

Tow unit with a GVW of 26,001 lbs. or more and a trail unit with a GVW or 10,001 lbs. or more = Class A CDL required if the vehicle is of a non-exempt category.

Feel free to PM me if you have any questions.

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