C149 was built in July 1941 at the Erie Railroad's Dunmore Shops. It was one of a series of 70 steel cabooses numbered C100 through C169 that were designed and built by the Erie. The Erie eventually merged with the Delaware, Lackawanna & Western Railroad to form the Erie Lackawanna (EL), and the EL merged again with several other lines to form Conrail in 1976. The C149 became Conrail class N-3 and was renumbered 46195. The car eventually made its way onto Wilmington & Western property, and was used at the end of W&W work trains. It was eventually refurbished during 2000 for use by passengers and Caboose Birthday Parties. It features a pressurized fire-fighting system on the rear platform for use when hot coals or cinders start small fires along the tracks. C149 entered revenue service on April 13, 2001.

In 2016, C149 was taken out of service to undergo a major interior restoration, which included a new toilet and enlarged restroom, a re-orientation of the cupola walkway and ladder, new electrical wiring and LED lighting, plus a fresh coat of paint.

Caboose C2013 was built by the Baltimore & Ohio's (B&O) Washington, IN, shops in 1926. The C2013 is one of 401 class I-5 cabooses once owned by the B&O. It was reclassified as I-5D when the car was rebuilt with cast frame trucks. The car has a steel underframe, ends and frame, with wooden side sheathing. Over the years, the C2013 has undergone many changes including the removal of its wooden underbody tool box, upgrading of the airbrake system, and the addition of toilets and water tanks which resulted in some of the car's original windows being sheathed over. Wilmington & Western volunteer shop crews have restored the car's original window placement, and have also added a back-up horn and lights for use during long back-up moves. In the summer of 2005, the C2013 entered our shops so that new roller-bearing trucks (wheel assemblies) could be installed and the aging wood siding replaced.

In 2016, C2013 underwent a top-to-bottom restoration. On the outside, the car was restored to an authentic B&O paint scheme, complete with dark-green window frames and sashes, a B&O capitol dome logo and the addition of authentic B&O window awnings. The interior was also refurbished with a modern toilet, new electrical wiring and LED lighting, new heater, and a fresh coat of paint throughout.

Caboose C2042 was built by the Baltimore & Ohio's (B&O) Washington, IN, shops in August 1926. The C2042 is one of 401 class I-5 cabooses once owned by the B&O. It was reclassified as I-5D when the car was rebuilt with cast frame trucks. The car has a steel underframe, ends and frame, with wooden side sheathing. Wilmington & Western volunteer shop crews have added a back-up horn and lights for use during long back-up moves.

In 2013, the C2042 underwent extensive exterior restoration, which included new exterior sheathing and new paint and lettering. In 2016, interior restoration was performed and included a new restroom, electrical wiring and lighting, new heater, woodwork repair, and a fresh coat of paint.