These buses were part of a joint order with Frederick City Transit, and shared the same paint livery.

In the fall of 1984, as the Washington Metro's Red Line extension to Shady Grove was complete, Ride On would see its largest route expansion to date.

Numerous routes would be added to accommodate passengers who would utilize the eight new metrorail stations along the western portion of Montgomery County.

In 2011, 12 of the Ride On's 40-foot Gillig Low Floor hybrid buses (5349–5360) and one clean diesel bus (5758) went into service.

Seven additional 40' Gillig Low Floor hybrid buses (5361–5367), which were also purchased with stimulus funds from the ARRA, went into service in mid-2012.

Also, the 2013 29-foot Gillig Low Floor clean diesel buses replaced all of the 2003 model shuttle transit vehicles (STV) that were formerly operated by Pittsburgh's Port Authority of Allegheny County.

And with the new buses came the new five-digit numbering system for Ride On, along with the addition of suffixes denoting engines with a ("C" for compressed natural gas, "D" for diesel, "E" for electric and "H" for hybrid).

Seventeen buses (44056D-44072D) are specially branded and used exclusively for Ride On's new extRa service that began October 2, 2017.

All of the 59 buses are manufactured by Gillig; 25 run on clean diesel (44056D-44080D) and 34 use compressed natural gas (44081C-44114C).

Ride On was award a $1.75 million grant from the Federal Transit Administration to purchase the county's first four electric buses and charging stations.

Ride On is partnering with Proterra, the bus manufacturer, and the Center for Transportation and the Environment, a nonprofit that develops technologies and implements solutions to achieve energy and environmental sustainability.

The Montgomery County Department of General Services, which purchases and maintains the Ride On buses, greatly assisted with the grant application.

The four Proterra Catalyst 35 ft electric buses are scheduled to serve Route 18 in Takoma Park starting in 2019.

On September 4, 2020, Ride On's first four fully-electric buses (43000E-43003E) entered service on the routes 18 and 25 in Silver Spring and Takoma Park.

These 2020 Gillig Advantage Diesel buses came with the new annocement narrator that repeats bus stop names twice.

In July/August 2023, Ride On brought back 3 of the 2008 40 feet Gillig Advantage Diesel buses from retirement (5737, 5744, and 5746) to operate for the Flash BRT service.

Between late June/July 2024, Ride On brought back the remaining 2008 40 feet Gillig Advantage Diesel buses from retirement (5726, 5728, 5730, 5732–5736, 5738/5739, 5742/5743, and 5745) due to the 2 new Ride On extRa routes "Lime" and "Pink" that operate between the Shady Grove metro station and Traville Transit Center.

On September 8, 2024, the first phase of the Ride On extRa Great Seneca Transit Network entered service with two new routes designated "Pink" and "Lime".

These limited stop routes operate daily between the Traville Transit Center and Shady Grove Metro Station.

In February 2025, RideOn brought back 2 of its 2009 40 feet Gillig Advantage Diesel buses (5753 and 5754) from retirement for the "ready reserve" fleet.

RideOn extRa is a bus service that started on October 2, 2017 with route 101,a limited bus stop service via Maryland Route 355 between Medical Center station on WMATA metro train's red line and the Lakeforest Mall Transit Center.

This bus route has free WiFi, USB charging ports, and more padding in the seats compared to traditional Ride On services.

Ride On Flex is an on-demand bus service that began serving Montgomery County on June 26, 2019, and runs in and around Rockville, Glenmont, and Wheaton using new, 11-passenger cutaway buses.

As with all other transit providers in the Washington Metropolitan Area, as of January 4, 2009[update], Ride On stopped the issue or acceptance of paper transfers.

Ride On operates a fleet consisting of Diesel, CNG, Diesel-electric hybrid, and Battery electric buses produced by Gillig Corporation, Nova Bus, Proterra, and Starcraft.

Training Units: Ready reserve fleet: 5726, 5728, 5730, 5732-5736, 5738/5739, 5742/5743, 5745, 5753/5754 Ride On offers 81 routes throughout Montgomery County.