The RIde On fleet was made up primarily of Gillig Phantoms at one time. Ride On ordered its first Gillig Phantoms in 1989, and ordered them again in 1994, 1995, 1996, 1997, and 1999. The last Gillig Phantom was retired from service in 2014.

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The Gillig Advantage/HEV demonstrator was tested by Ride On in June 2004. Five were purchased and entered service in May of 2006. They were renumbered in 2009 when a large influx of hybrids to the fleet would have prevented Ride On from maintaining its current numbering scheme. All the hybrids operate from the Silver Spring garage.

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After purchasing several orders of hybrid Gillig Advantages, Ride On purchased diesels. The first of these buses arrived in 2008. They feature frameless windows and were the first buses since the 2001-2002 Orion Vs to be delivered in the "standard" blue and white Ride On paint scheme. Ride On has since ordered additional 40 foot diesel Gillig Advantage buses that came in the new blue/yellow/green scheme. These buses operate from both Silver Spring and Gaithersburg garages. In 2017, Ride On accepted delivery of Gillig Advantage units with BRT styling for its "Ride On Extra" limited stop service. These buses also feature a special paint scheme, WiFi, USB ports for charging mobile devices, interior screens to display the next stop and other service information, and other features.

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Ride On ordered its first Gillig Advantage CNG buses in 2014 to replace the aging 40 foot Orion V/CNG buses. While Ride On has been a regular customer for Gillig buses for many years, Gillig only began manufacturing CNG buses shortly before this. Therefore, Ride On had turned to Orion and New Flyer for CNG buses prior to this order.

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These buses were initially purchased to replace some of the cutaways operating out of the Nicholson Court garage in 2008. Following subsequent orders, Ride On now has nearly 100 of these buses and they serve each of Ride On's three garages.

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Ride On operated many Orion I buses starting in 1984 and through the final Orion I's retirement in 2013. All of the Orion Is in Ride On's fleet were 30 footers, but five of them were unique for having larger "hammerhead" destination signs.

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Ride On has had many 35 foot Orion V buses in its fleet over the years. The first two 35 foot Orion Vs arrived in 1993 and had specifications very similar to the 1991 Orion Is. Additional Orion Vs of this length were ordered in 1996, 1998, 2001, and 2002. All of these buses have been retired as of 2016.

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Ride On ordered its first three compressed natural gas (CNG) buses in 1996. These buses operated from the Gaithersburg garage for their entire careers. In the mid-2000s, they were renumbered to better fit in the fleet numbering scheme after the arrival of the Orion VII/CNGs. These buses are no longer in service.

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These were the first low floor buses in the Ride On fleet. Neither bus was originally owned by Ride On, as they were ordered for a transit authority in Quebec that rejected them. They were originally numbered 5570 and 5571 and were painted green and white with the cloud wrap. They were often not in revenue service and were officially retired in the mid-2000s.

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Ride On ordered its first 40 foot buses in 1999 as an order of diesel powered Orion Vs. These buses started out at Silver Spring garage, but were ultimately transfered to Gaithersburg garage towards the end of their careers. As of late 2015, two remain in service; the rest have been retired.

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Ride On's CNG fleet grew significantly when these buses were ordered and arrived in 2000. They operated upcounty on the Gaithersburg garage routes until their retirement upon the arrival of the Gillig Advnatage/CNG buses in 2014.

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Ride On ordered Orion VII/CNG buses to operate at its Gaithersburg Garage in 2003 and again in 2006. The 2003 procurement was Ride On's largest order of low floor buses in its history at that time. These were the last CNG buses to be delivered in the "traditional" green and yellow scheme that the CNG buses wore.

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Ride On ordered New Flyer buses for the first time in 2005, when it purchased additional CNG buses from the company for its Gaithersburg garage. To date, this is the only time Ride On has purchased New Flyers. These buses operate from the Gaithersburg Garage.

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The four Flxible Metro-D buses Ride On had in its fleet were originally powered by Liquid Natural Gas (LNG) and were operated by the Maryland MTA. Upon their arrival in Montgomery County, they were repowered with diesel engines and then assigned to the Gaithersburg garage. They had more seats than any other Ride On bus model, and as a result, were frequently assigned to Route 70, where Ride On management prefers not to have standees for that route's long express segment on I-270.

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Following the unexpected and sudden retirement of the Champion cutaway buses after those buses caught on fire, Ride On took possession of WMATA's 30 foot Orion Vs. WMATA had already retired these buses from its own fleet at the time Ride On partially repainted them in the new blue/yellow/green Ride On scheme and renumbered them to fit the county's fleet numbering system. They remained in service with Ride On until the fall of 2014, when a new order of 30 foot Gillig Advantages arrived, leading to the ex-WMATA Orion units' retirement.

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Ride On historically operated a variety of cutaway buses on its lower volume routes. Prior to the late 2000s, the cutaway buses' operation would be contracted to outside firms, but Ride On eventually took this operation in house. The cutaways tended to have shorter service lives than the standard buses and have all been replaced by 30 foot Gillig Phantom buses.

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The Bethesda Circulator was formerly Ride On Route 92 and nicknamed the Bethesda 8 for its route (a funny looking figure eight) and its frequency of service (every 8 minutes), began service in September of 1999. Its mission was to take people from the Bethesda Metro and county operated parking garages to points in the Bethesda Central Business District. It ran between 7:30 AM and 7:30 PM on weekdays and no fare is collected. The route was originally operated by WMATA with Flxible Metro-Bs painted in the Ride On paint scheme with signs and flags for the Bethesda 8. The operation of the route was later shifted to Ride On's Silver Spring Garage and the county took over the route's operation. Again, certain buses had Bethesda 8 signs and flags applied to the bus. Two Orion Vs ran the route until March 2001. The service was also adjusted to begin and end 30 minutes earlier. Then, Montgomery County unveiled special trolleybuses for this service. The trolleys had wood finishes and seats, round light bulb globes to illuminate the interior, and an open air rear platform. This was done to attract more ridership to the route. The county said once more trolleys arrive, weekend service would commence. Once weekend service began, the Behesda 8 ran at 8 minute intervals from 7:00 AM until midnight on weekdays, until 2 AM Friday nights (Saturday mornings), and from 6 PM until 2 AM on Saturdays (Sunday mornings). Service has also been provided for special events, such as the Taste of Bethesda. During parts of 2002, the route was operated with the Orion Is and starting September 1, 2002, with ATE/Ryder cutaways. In early 2007, the operation of the route was transferred to the Bethesda Urban Partnership, which purchased new trolleys to operate on the route. Later, the second group of trolleys were replaced by more traditional buses. On January 4, 2016, the first change to the Bethesda Circulator's route since the route's original inception will take place, as the route is modified to include Battery Lane and Bradley Boulevard.

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