5 Lessons Learned from 50 Years of Drayage

For over 50 years, ContainerPort Group (CPG^®) has been at the forefront of drayage logistics, navigating industry shifts, economic cycles, and supply chain disruptions. We’ve learned what works, what doesn’t, and what truly matters when it comes to moving freight efficiently. Here, we share five lessons we've learned from over 50 years in drayage.

Top Five Lessons from Five Decades in Drayage 

1. Drayage Isn’t Just Trucking, It’s Supply Chain Strategy
   Many companies treat drayage as a minor cost, but experienced shippers know it's a critical link that impacts every part of the supply chain—from port efficiency to final-mile delivery timelines. Poor drayage planning can lead to congestion, delays, and higher landed costs.
   
   When containers sit too long at the port or aren't unloaded in time, shippers can face steep demurrage or detention charges. Failing to plan for chassis availability can result in delays, extra fees, or last-minute repositioning costs. Late or missed pickups can lead to extra storage fees at port or rail facilities, especially when tight appointment windows are involved. Disorganized drayage also risks downstream disruption, like delays in warehouse receiving or outbound fulfillment. When things go off track due to lack of planning, shippers are often forced to expedite the freight via air or long-haul alternatives, at a much higher rate, just to stay on schedule.
   
   The most successful BCOs and logistics managers treat drayage as part of a holistic strategy—optimizing routes, reducing dwell times, and integrating drayage with warehousing, transloading, and final-mile delivery. Choosing the right drayage provider reduces delays, improves container flow, and lowers total costs.
   
   A great drayage partner acts as an extension of your team, communicating clearly, taking ownership of outcomes, and solving problems before they become emergencies. They should monitor container availability and free time closely, helping you avoid demurrage and detention fees by prioritizing timely pickups and returns. A top provider, like ContainerPort Group, should have access to dedicated chassis pools or strong relationships with leasing companies, ensuring availability when and where it’s needed. They should also know the ins and outs of port and rail terminals, securing appointment slots, managing driver turn times, and avoiding storage fees through local knowledge and coordination. Additionally, look for providers that offer warehousing, transloading, and final-mile options to give your supply chain more agility and fewer handoffs to manage.
   
   
2. Relationships Matter More Than Rates
   Over the years, we’ve seen that the cheapest provider isn’t always the best. Yes, cost is always a factor in logistics decisions, but drayage is an industry where relationships often drive long-term success. Shippers who prioritize long-term relationships with reliable partners avoid last-minute capacity issues, peak season surges, and service disruptions.
   
   Strong relationships lead to better communication, faster problem-solving, and a higher level of service consistency. When you have a true partnership, your provider understands your business, anticipates your needs, and prioritizes your freight when capacity is tight or disruptions occur. They’re not just filling a load—they’re helping you protect your brand, meet delivery windows, and reduce risk across the supply chain. 
   
   In volatile markets—where rates, capacity, and conditions can change overnight—relationships provide stability. A reliable drayage partner that understands your business can help you navigate port congestion, secure chassis, and adapt to unexpected changes. In times of disruption, whether it’s labor strikes, capacity crunches, or regulatory shifts, having strong carrier partnerships is worth more than saving a few dollars per haul.  A provider who’s invested in your success will go the extra mile to offer creative solutions, allocate resources, and help you stay ahead of challenges. That kind of commitment can’t be captured in a rate sheet.
   
   
3. Flexibility Wins in a Changing Market
   In a market defined by uncertainty, think labor strikes, chassis shortages, port congestion, or shifting demand, rigid supply chains break. Flexible ones bend and adapt.
   
   The providers that thrive are the ones that can adapt quickly, whether that means expanding geographic coverage, offering alternative routings, or pivoting to handle unexpected volume spikes. When your drayage partner is flexible, they can shift capacity, reroute freight, adjust timelines, or tap into alternative ports or services at a moment’s notice. This agility helps you keep freight moving when others are stalled, avoid costly delays, and meet customer expectations even in volatile conditions.
   
   Flexibility also gives you options. Instead of being locked into a single solution, you can pivot quickly by scaling up during peak season, responding to volume surges, or adjusting to new service requirements. It helps reduce risk, improve speed, and create a more resilient supply chain overall. Companies that build flexibility into their supply chain, including diversifying their port gateways and using a variety of capacity options, will be better prepared for market fluctuations.
   
   Bottom line: in a constantly changing environment, the most adaptable players don’t just survive, they lead.
   
   
4. Tech Has Changed the Game, But Execution Still Wins
   There’s no doubt that technology has transformed the drayage industry. From real-time tracking, digital freight matching, and AI-powered analytics, today’s tech tools make operations smarter, faster, and more efficient. However, technology alone isn’t enough—execution is what separates the best providers from the rest.
   
   Shippers now expect visibility, automation, and seamless data flow as table stakes. But here’s the truth: technology alone doesn’t move freight, people do. When containers get rolled, chassis are unavailable, or terminals are backed up, it's not the software that solves the problem, it's the operations team behind it.
   
   The providers that win aren’t just the ones with the flashiest dashboards, but the ones who combine great tech with boots-on-the-ground expertise, strong carrier networks, and proactive communication. Execution means anticipating issues before they impact your supply chain. It means getting containers out of congested ports, resolving exceptions fast, and keeping your freight moving—day in and day out. At CPG, we combine tech-driven visibility with a hands-on operations team to ensure your freight keeps moving.
   
   
5. The Next 50 Years Will Be Built on Data & Automation
   The drayage industry is entering a new era—one driven not just by trucks and terminals, but by data, intelligence, and automation. As global supply chains become more complex and customer expectations rise, the ability to make faster, smarter, and more proactive decisions is becoming a true competitive advantage.
   
   As drayage moves forward, data-driven decision-making and automation will play an even bigger role. From predictive analytics that anticipate congestion to AI-powered dispatching that optimizes routes in real time, the future of drayage will be about smarter, faster and more efficient operations.
   
   But technology alone isn’t the end goal, it’s what you do with it that matters. The real opportunity lies in how shippers and providers use data to create smarter supply chains, ones that are more agile, cost-effective, and resilient. Whether it’s reducing dwell time, avoiding detention, or optimizing multi-leg container moves, data and automation are the levers that will drive continuous improvement over the next 50 years. Shippers and providers that invest in these innovations today will have a competitive advantage as the industry continues to evolve. 
   
   

Reflecting on 50 Years: The Future of Drayage Logistics

As we reflect on 50 years in the drayage industry, one thing remains clear: shippers who invest in strong, strategic partnerships gain a competitive edge, not just in moving freight, but in navigating complexity, managing risk, and driving long-term growth.

The future of drayage logistics will be shaped by continued advancements in technology, shifting global trade patterns, and the ongoing need for flexibility and resilience. Technology will continue to play a key role, but so will adaptability—helping businesses respond to disruptions and rising customer expectations.

At CPG, we are committed to staying at the forefront of these changes, continuously innovating and adapting to meet the needs of our clients. We’re doubling down on the principles that have sustained us for five decades: deep industry knowledge, dependable service, and a commitment to continuous improvement. By leveraging our extensive experience, strong relationships, and cutting-edge technologies, we are well-positioned to lead the industry into the next 50 years and beyond.

Are you ready to work with an experienced partner who’s evolved with the industry? Let’s connect and explore how we can support your logistics needs with comprehensive drayage solutions.

Also, check out our insights on what to look for in a drayage RFP and and consider including CPG in your next round!