NO! Another long lived myth. The enlisted compliment of the 1st USV were equipped with M1896 Krag Carbines, and all accouterments for that weapon. While officers were allowed to purchase their own weapons, the only Winchester 1895 that has been documented to the 1st USV was Roosevelts personnel weapon, loaned to a corporal acting as his aide. Only armed company's were allowed on the ship to Cuba. With that one documented exception, if you did not have a Krag, you did not go. NO enlisted man carried a private purchase weapon in Cuba.
Later in the campaign, mail was received, some private purchase non regulation items made an appearance. But when they disembarked in Daqueri, they wore regulation M1884 uniforms, with regulation Double Row Mills belts, shouldering M1896 Krag Carbines.
Both Roosevelt and Leonard Wood made sure that the Regiment was equipped as a regular regiment, as they knew only such a unit would be sent to Cuba. Indeed, the 1st USV would be the only USV regiment in Cuba prior to the surrender of Santiago.
The M1895 potato diggers were a gift to the regiment, and special detachments were set up for them. If you were on the MG detachment, you gave up your Krag to someone else. The MG detachments probably carried reissued Colt Artillerys for sidearms.