History

From Humble Beginnings

The Evolution of Ruppert Landscape

Craig’s parents’ garage where he started the business circa 1970

In the early 1970s, a young Craig Ruppert had a simple goal: earn enough money to buy a car and have some spending cash. Armed with a push mower and a strong work ethic, he started knocking on doors in his neighborhood, offering to mow lawns. With his parents’ garage as his headquarters, what started as a side hustle quickly grew into something bigger than he ever imagined.

As the demand for his services increased, Craig hired a few friends, including his brother Chris, to help keep up. With each job, he was learning—about landscaping, about business, and about the value of hard work. Mistakes were made, lessons were learned, and slowly but surely, the business took root.

Craig Ruppert in the early days of the company

The first decade wasn’t easy. There were setbacks, long days, and plenty of trial and error. But one thing became clear: success wasn’t just about cutting grass; it was about taking care of people. By treating employees with respect and giving them opportunities to grow, Craig saw firsthand how they, in turn, took great care of their customers. That simple principle became the foundation of everything that followed.

Over the next five decades, Ruppert Landscape evolved from mowing neighborhood lawns to building and maintaining some of the most complex landscapes in the country. Residential yards gave way to large-scale developments, parks, and corporate campuses. What started with a focus on hustle and efficiency expanded to include deep horticultural knowledge, technical expertise, and a relentless commitment to quality.

Today, Ruppert Landscape is a thriving company with over 2,500 employees across 50 branches, serving clients throughout the Northeast, Mid-Atlantic, and Southeastern U.S. The core values that fueled its early success—hard work, integrity, and a people-first mindset—remain at the heart of the business. While the scale of the work has grown, the mission is the same: build something great, take care of your people, and always strive to do better than the day before.

Ruppert By the Decades

1970s

  • The company came into being in the early 70’s with Craig Ruppert cutting lawns in the neighborhood to make money.
  • In 1976, the company incorporated and became Ruppert Landscape Company.
  • The customer base was largely residential, with some focus on commercial contracts and Christmas tree sales during the holidays
  • Having outgrown the Rupperts’ basement and garage, the business was relocated to the backyard of Craig’s first home in Colesville, MD.
  • There were between 5-10 employees during this period (several full-time field managers) and we hired our first administrative assistant.
  • We chose our “Ruppert green” color at the Duron Paint store and painted our first truck, marking the very beginning of our focus on image.

1980s

  • We converted to all commercial contracts during this decade, giving away our remaining residential contracts to local competitors.
  • We began entering local and national awards programs to improve quality, sharpen skills and gain recognition for our work; and encouraging our team to explore certifications and educational opportunities that would raise our technical acumen.
  • An economic recession caused increased competition for work and forced us to reduce overhead and increase efficiency. To create better awareness around costs and productivity, we increased our financial meeting frequency and adopted the open-book philosophy of sharing information at all levels.
  • The business moved to Rice Manor in Ashton, MD, a location that would serve as the company’s headquarters for the next 18 years.
  • We operated an installation and maintenance branch out of the Maryland and newly opened office in Virginia, which marked the beginning of our branching structure and was the foundation for our decentralized approach to create autonomy and decision-making ability at the local level.
  • We had many “firsts” during this decade including hosting our first Field Day and our first Management Development Day, and we formalized our Board of Advisors.

1990s

  • We opened 10 branches: our environmental branch (MD) that specialized in ecological restorations; seven landscape maintenance branches in Forestville (MD), Atlanta (GA), Newark (DE), Baltimore (MD), Chantilly (VA), Richmond (VA), and Frederick (MD); and two landscape installation branches in Atlanta (GA) and Baltimore (MD).
  • We built custom facilities in Gainesville, VA and Forestville, MD, which were our first foray into designing facilities and yard/shop space where we could work efficiently and showcase our image as a professional service provider.
  • While most of our growth was organic, we acquired several companies during this period that enhanced our ability to efficiently service customers in both existing and new markets.
  • Our sister company, Ruppert Nurseries, was born with the purchase of equipment, field inventory, and nurseries associated with one of those acquisitions, J.H. Burton and Sons, Inc.
  • We began incorporating community service into our Field Day (1992), holding our first off-site event benefitting a park in DC.  We performed subsequent Field Day events in every year between 1993-1998.
  • We formalized our training program in 1994, developing an orientation program for new employees and ongoing training for existing employees on safety, equipment, and horticulture practices.
  • In 1998, Ruppert Landscape services and equipment were sold to Servicemaster (TruGreen-ChemLawn) during a period of industry consolidation. Ruppert Nurseries was retained and continued to operate under Ruppert management; the sale did not include the physical properties.

2000s

  • From 1998-2003, Ruppert Nurseries was expanded, and Ruppert Properties and Ruppert Ventures were founded. This period enabled an increased knowledge in many business areas as well as a greater opportunity for time with family and community.
  • Based on perceived opportunities with customers and former employees and with the help of many returning key leaders from the original Ruppert Landscape, the company reentered the industry under the Ruppert Nurseries name in 2003.
  • There was rapid growth during this period and we opened 11 branches: eight landscape maintenance branches in Laytonsville (MD), Toughkenamon (PA), Lilburn (GA), Gainesville (VA), Forestville (MD), Frederick (MD), Charlotte (NC) and Baltimore (MD); and three landscape installation branches Laytonsville (MD), Atlanta (GA) and Gainesville (VA).
  • The company was recognized on the Inc. 500 list with a 659.9% three-year growth since re-entering the industry (2003-2005).
  • The company made large investments in information technology to help scale operations, including IT personnel, hardware, and software.
  • The organization and management team were once again recognized for their growth, philanthropy (contributing over $1.3M during this period), business ethics and processes, and quality projects.
  • Anticipating future growth, we built a new LEED certified corporate campus designed to accommodate expansion for the next 15 years. The campus design created a cleaner, brighter, temperate, and functional environment for employees and showcased our commitment to environmental sustainability with features like a solar farm that completely offset the site’s electrical demand.
  • In 2009, the company reclaimed the name and incorporated as Ruppert Landscape.

2010s

  • This period was marked by significant growth. We opened 12 branches—10 landscape maintenance branches in Richmond (VA), Raleigh (NC), Alexandria (VA), King of Prussia (PA), Washington (DC), Mableton (GA), White Marsh (MD), Fredericksburg (VA), Richmond South (VA), Camp Hill (PA), and two landscape installation branches in Raleigh (NC) and Houston (TX).
  • The company was being consistently recognized on regional and industry “top” lists for its growth and garnered over 125 industry awards for outstanding, high-quality projects.
  • We continued to pursue large, full-scope landscape installation projects including Myriad Gardens (OK), The National Museum of African American History and Culture (DC), MGM National Harbor (DC), and Mary Elizabeth Branch Park (TX).
  • We continued to invest in IT solutions to simplify our business processes and provide our team with timely and easy to access information which makes them more efficient.
  • We contributed over $3.5 million to help support people and groups in need through our charitable giving efforts and hosted several Field Days renovating Baltimore’s Carroll Park (2014), The Armed Forces Retirement Home or “Old Soldiers Home” in Washington, DC (2015,) the Children’s Home in Catonsville, Md. (2016) and Corpus Christi Catholic Church in Stone Mountain, GA (2018).

2020s

  • In early 2020, we faced the start of COVID-19 pandemic. We were deemed an essential business and were able to remain largely operational but had to rethink processes and protocols to ensure employee and customer safety and deal with supply chain disruptions.
  • We continued our Field Day tradition with charitable giving events at the Children’s National Research & Innovation Campus in Washington, D.C. (2021) and the Long Branch Community Center in Silver Spring, MD (2022).
  • We continued to pursue large, full-scope landscape installation projects including Scissortail Park (OK), American Airlines Robert L. Crandall Campus (TX), and Norfolk Southern Headquarters (GA).
  • In December of 2022, we announced our strategic partnership with Knox Lane, a growth-oriented investment firm that is focused on partnering with businesses in the services and consumer sectors. This partnership supports our long-term vision to continue to grow the company’s footprint within current and adjacent markets and expand organically and through strategic acquisitions. The company’s management team, led by Craig Ruppert (Executive Chairman of the Board) and Phil Key (CEO), will continue to lead Ruppert Landscape and remain significant minority owners in the business.
  • Ruppert acquired Scott’s Landscaping (State College, PA), The Greenery of Charleston (SC), Tree Amigos Outdoor Services (Jacksonville/Orlando, FL), Lawnscapes (Panama City, FL), and Ocean Woods Landscaping (Hilton Head, SC). These partnerships allowed us to expand into new markets, brought outstanding talent to the Ruppert team, and provides even more opportunity for our people.
  • Through organic growth, we’ve added a landscape installation branch in Nashville (TN) and 12 new landscape maintenance branches in Delmarva (DE), Richmond East (VA), Wilmington (DE), Durham (NC), Dulles (VA), Alpharetta (GA), Silver Spring (MD), Apex (NC), Elkridge (MD), Annapolis (MD), Fairfax (VA), and Athens (GA). Ruppert Landscape now spans 50 branches across nine states with over 2,500 team members.