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Cross-Border Trucking: The Great Canadian–American Road Trip

Moving freight across the border between Canada and the United States sounds straightforward enough: load a truck, hand over the paperwork, flash a smile at the customs officer, and off you go. Except… not quite.

In reality, cross-border trucking is a finely tuned, regulation-heavy dance between logistics planning, customs clearance, and problem-solving on the fly. And unlike a leisurely summer road trip, this one doesn’t allow for scenic detours, not unless you like fines, shipment delays or having your goods sent back to where they came from.

For shippers and manufacturers, partnering with the right cross-border trucking company can mean the difference between delivering on time and delivering excuses. That’s where Bowline Logistics comes in. But before we get to that, let’s talk about why cross-border freight transport is a whole different beast.

Why Cross-Border Trucking is Not Just “Domestic Plus Paperwork”

Domestic freight transport has its challenges – scheduling, load security, equipment maintenance – but the moment you add an international border, the complexity increases exponentially. Cross-border logistics involves navigating two sets of regulations, customs requirements, and carrier responsibilities.

When your freight is moving from Saskatchewan to South Dakota or from Vancouver to Vegas, your trucking partner needs to:

  • Understand customs clearance procedures for both Canada and the USA.

  • Be equipped for international freight shipping, including USMCA/NAFTA documentation.

  • Manage carrier licensing and insurance in two countries.

In short: cross-border freight solutions demand both experience and precision.

Customs Clearance: The Gatekeeper of Cross-Border Logistics

Ask any veteran in Canada-US freight transport what slows a shipment down, and “customs clearance” will almost always top the list.

The process requires more than a commercial invoice and a handshake. You’ll need:

Bill of Lading (BOL)

The master document of the shipment. Think of the Bill of Lading as the freight world’s version of a boarding pass, ID, and contract all rolled into one. It’s issued by the carrier to the shipper and serves three big purposes:

  1. Receipt of Goods: Confirms that the carrier has received the freight in good order.

  2. Contract of Carriage: Lays out the agreed terms for transporting the goods from origin to destination.

  3. Document of Title: Proves who legally owns the goods while they’re in transit.

For cross-border trucking companies, accuracy here is non-negotiable. Every detail from the shipper’s and consignee’s names to the freight description, weight, and quantity must be spot on. If the BOL says “10 pallets” and customs counts 11, you’re about to have a very long day at the border.

Commercial Invoice

If the Bill of Lading says what’s moving, the Commercial Invoice explains what it’s worth. Customs officers care a lot about that number. This document details:

  • The seller’s and buyer’s full information.

  • A complete description of the goods.

  • Quantities and unit prices.

  • The total value of the shipment.

  • Currency of sale.

  • Incoterms (who’s responsible for freight, insurance, and duties).

Why so much detail? Customs uses the Commercial Invoice to calculate duties and taxes, verify compliance with trade agreements, and make sure you’re not undervaluing goods to sneak in under tariff thresholds. One missing or vague line here can cause your Canada-US freight transport to grind to a halt.

Certificate of Origin

Under the United States–Mexico–Canada Agreement (USMCA), certain goods qualify for reduced or zero tariffs, but only if you can prove where they were made.

This document certifies that the goods meet the agreement’s rules of origin. It needs to be completed accurately and kept on file (often for up to five years) in case customs decides to audit. For example, a Saskatchewan-manufactured piece of farm equipment heading to North Dakota could move duty-free if the Certificate of Origin is in order. Without it? You’re paying full duties, and the competitive pricing advantage is gone.

Customs Broker Coordination

Customs brokers are like translators between your business and the ever-changing, acronym-heavy world of border regulations. They handle:

  • Assigning the correct Harmonized System (HS) codes.

  • Filing customs entries electronically.

  • Calculating duties, taxes, and fees.

  • Liaising with customs officials to smooth out any issues.

In cross-border logistics, a seasoned customs broker is the difference between a truck rolling through the port of entry and one parked for hours while drivers re-fax paperwork (yes, fax still exists at some borders). Top cross-border trucking companies like Bowline Logistics work closely with trusted brokers, often having them pre-clear shipments with tariff codes before the truck even arrives at the crossing.

Without the right customs brokerage for trucking companies, shipments risk being held, inspected or outright denied entry. A carrier like Bowline Logistics, which integrates customs procedures into its operations, can keep freight moving instead of sitting idle at the border.

Paperwork: The True Border Patrol

For cross-border trucking companies, paperwork is more than a formality — it’s the lifeline of the operation. The smallest mistake in a Harmonized System (HS) code or mismatch between documents can trigger delays, extra costs, or, in extreme cases, seizures.

Pro tip: Triple-check paperwork before the truck leaves the yard. It’s much easier to correct a PDF than a truckload of goods parked on the wrong side of the border.

Regulatory Differences That Keep Drivers Awake at Night

Rules change the moment wheels cross the border. Canadian drivers entering the U.S. must comply with Federal Motor Carrier Safety Administration (FMCSA) regulations, while American drivers heading north must meet Canadian safety, insurance, and compliance requirements.

Some differences include:

  • Hours of Service (HOS): Limits on driving time and rest breaks vary.

  • Insurance Minimums: Liability requirements differ between countries.

  • Weight Limits: Axle weight and total gross vehicle weight standards vary by state and province.

These aren’t “guidelines” — they’re hard requirements, and failing to follow them can stop a shipment in its tracks.

Freight Types That Need Special Attention

Not all freight is created equal in the eyes of customs and transport laws. Some types of loads require additional documentation, permits, or handling protocols:

LTL Cross-Border Shipments

Multiple customers’ goods in one truck require meticulous documentation for each shipment.

Oversized Cross-Border Loads

Think wind turbine blades or heavy machinery. These require special routing, permits, and sometimes escorts.

Temperature-Controlled Cross-Border Freight

From fresh produce to pharmaceuticals, any break in the cold chain can spell disaster.

Dangerous Goods

Flammable, toxic, or otherwise hazardous freight must meet both Transport Canada and U.S. Department of Transportation standards.

The High Cost of Getting It Wrong

If a shipment is delayed or turned back at the border, it’s not just the delivery that takes a hit, the ripple effects can be costly and far-reaching. Missed deadlines with downstream customers can throw entire schedules into chaos, while storage and demurrage fees quickly add up, eating into profit margins. On top of that, every delay chips away at your reputation with buyers and partners, eroding trust that took years to build. In a cross-border supply chain, even a 24-hour setback can derail production timelines, making the choice of a cross-border trucking company one of the most critical decisions in your logistics strategy.

Why Choosing the Right Cross-Border Trucking Company Matters

Here’s the thing, anyone with a truck and a passport can technically move freight across the border. But only a select few can do it with the efficiency, compliance, and reliability that keeps your supply chain humming.

A great cross-border freight transport partner will:

  • Operate as a bonded carrier for faster border clearance.

  • Maintain close relationships with customs brokers.

  • Offer route planning that optimizes both speed and compliance.

  • Have drivers experienced in international freight shipping, not just domestic.

Why Bowline Logistics is Your Best Bet for Canada–U.S. Freight Transport

Bowline Logistics isn’t just another name on the list of cross-border trucking companies, we’re the partner you want when your freight’s destination crosses national lines.

Here’s why:

  • Bonded Carrier Status: We can move goods through customs-controlled areas without paying duties immediately.

  • Heavy Haul & LTL Expertise: From oversized industrial machinery to partial loads, we’ve hauled it all.

  • Seamless Canada–U.S. Coverage: Coast-to-coast in Canada and deep into the U.S. — no outsourcing to unknown carriers.

  • Proven Compliance: Our team knows the regulations inside and out, keeping freight moving without costly hiccups.

Whether it’s a single load from Calgary to Colorado or ongoing cross-border supply chain support, we combine industry know-how with the personal service that keeps shippers coming back.

Your Freight Deserves a First-Class Border Crossing

Cross-border freight shipping is not the place for trial and error. Every delay, every missing document, every overlooked permit eats into your margins and erodes customer trust.

Bowline Logistics brings the experience, compliance expertise, and on-the-ground network to make cross-border trucking simple, or at least as simple as moving goods internationally can be.

So, if you’re ready to keep your Canada-U.S. freight moving without the drama, sign-up for a Free Quote from Bowline Logistics. We’ll get your load where it needs to go, when it needs to get there and we’ll make crossing that border look easy.

ABOUT THE AUTHOR

Michelle Green – Project Sales & Business Development

Michelle Green, Project Sales and Business Development - Bowline Logistics

Michelle is known for her deep industry knowledge, customer-first approach, and creative problem-solving in complex logistics environments. With a background in fluid power technology and commercial diving, Michelle brings a hands-on mindset and technical edge to every project. Whether coordinating time-sensitive freight or supporting large-scale industrial moves, she plays a vital role in building trust with clients and driving growth across North America.

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Bowline Logistics Welcomes Delly McEwan as Chief Executive Officer

Spruce Grove, AB (May 30, 2025) – Bowline Logistics Ltd. is proud to announce the appointment of Delly McEwan as Chief Executive Officer, effective June 2, 2025. A seasoned executive and logistics strategist, McEwan brings over 25 years of experience in transportation, business development, and project execution across North America.

Bowline welcomes McEwan, following an impressive career that includes founding NexGen Transportation and serving as its President for 13 years, serving as a Managing Director in the wind construction industry, and leading a large First Nations Development Corporation as its CEO. His corporate journey also includes senior roles with Kuehne + Nagel, Bechtel, Bantrel, and Air Liquide Global Energy Solutions. Beyond the boardroom, Delly also serves as the Board Chair of Little Warriors, a national charity committed to the awareness, prevention, and treatment of child sex abuse and sits on the Parkland County Economic Diversification Committee.

 Having had the opportunity to learn from many of the best in the industry—while also successfully founding and building a transportation company—McEwan brings a unique perspective to Bowline’s dynamic and growing team. His executive leadership across diverse industries such as renewable energy, specialized crane and rigging, construction, and corporate development, positions him well to help guide Bowline through the next phase of growth. His fresh outlook is a welcome addition as Bowline continues to evolve its service offerings and reinforce its long-term path toward sustainability and operational excellence.

“I was drawn to Bowline because it’s a company with a strong, people-first culture,” McEwan shared. “I believe in leadership that empowers those on the front lines. The individuals doing the work every day are the most valuable asset of any successful organization—and I saw a kindred spirit in Bowline’s approach. I’m excited to be part of a team that values every voice and puts service excellence at the heart of everything we do.”

McEwan’s leadership style is collaborative, analytical, and deeply team-focused. His strategic vision will help guide Bowline through its next phase of innovation in the transportation and logistics sector, with a particular eye toward building a comprehensive, asset-based logistics solution for the North American market. He is especially looking forward to sharing his broad experience in all aspects of transportation and executive management while integrating into Bowline’s best-in-class culture.

“Delly brings a wealth of knowledge, integrity, and forward-thinking leadership to our organization,” said Tyler Boyd, Founder and President of Bowline Logistics. “His experience and passion for building teams align perfectly with the direction we’re headed. I look forward to working alongside him as we continue expand Bowline’s presence across borders and into new markets.”

Delly McEwan - CEO - Bowline Logistics

McEwan resides in Spruce Grove, Alberta, with his two daughters, aged 9 and 13. He holds a Project Management Certificate from the Southern Alberta Institute of Technology (SAIT) and remains actively involved in both industry and community initiatives.

As Bowline continues to expand its reach and services across North America, the addition of Delly McEwan to the leadership team marks a pivotal moment in the company’s journey—anchored in collaboration, operational excellence, and a commitment to serving both its clients and its people.

About Bowline Logistics Ltd.
Bowline Logistics is a Canadian-owned transportation company specializing in open-deck, heavy haul, and project cargo solutions across North America. From multi-axle RGNs and extendables to step-decks and ramp-equipped trailers, our fleet is built to handle complex freight requirements with precision and flexibility. We serve a wide range of industries—including energy, construction, mining, and modular manufacturing—delivering tailored logistics solutions that go beyond the standard.

At Bowline, we believe logistics is still a people business. Our team-first culture is rooted in accountability, collaboration, and a deep respect for the individuals doing the work—whether behind the wheel, in the office, or at the job site. With a focus on long-term relationships and service-driven results, Bowline is redefining what it means to deliver in today’s logistics industry.

Media Contact:
Michelle Green
Project Sales & Business Development
Bowline Logistics Ltd.
mgreen@bowlinelogistics.com
www.bowlinelogistics.com

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Finally, A Trusted and Reliable Trucking Company in Canada

In a world where transportation can feel impersonal and transactional, Bowline Logistics is rewriting the rulebook. As a trusted trucking company based in Canada, Bowline does more than move freight, they build lasting partnerships that drive value far beyond the delivery point. With deep roots across North America and a reputation for reliable transportation, Bowline is the go-to choice for businesses that want more from their transportation services.

Their tagline says it all: “When reliability matters most.” And for Bowline, that’s not just a slogan—it’s a promise.

Long-Term Transportation Relationships Across Canada and the USA

In an industry where speed often overshadows service, Bowline Logistics puts people first. Rather than chasing one-time transactions, they focus on building long-term relationships with clients across Canada and North America. From major cities like Edmonton, Calgary, and Vancouver to remote delivery points, Bowline’s success stems from being a trusted partner—not just a vendor.

Clients know they can count on Bowline not just once, but every time. Their team takes the time to understand your business, anticipate challenges, and offer customized logistics solutions that grow with your goals.

Trusted Transportation Services Backed by a Dedicated Team

Bowline’s strength lies in the expertise and dedication of its people. With years of experience in the transportation industry, their dedicated team ensures each load is planned, tracked, and delivered with care. They don’t just meet expectations—they exceed them.

That trust is reinforced by Bowline’s industry-leading certifications, robust safety standards, and dependable service record. Bowline ensures every job of oversized freight meets the highest standards of safely, efficiency, and reliability.

Trucking Solutions for FTL, LTL, and Long-Haul Freight

Whether you’re shipping full truckloads (FTL), less than truckload (LTL), or need long-haul capacity across provinces or international borders, Bowline has the fleet and expertise to deliver. Their modern trucks are maintained to the highest standards, and their route planning ensures optimal transit times and minimized risk.

As businesses navigate shifting markets and rising transportation costs, Bowline offers cost-effective options that don’t cut corners on quality. Their focus is on delivering value—both in pricing and performance—to meet your current and future transportation needs.

Cross-Border and North American Freight Transportation

Shipping goods across the U.S.–Canada border can be a challenge, but not with Bowline. Their cross-border expertise ensures documentation, compliance, and timing are all handled seamlessly. Businesses operating across North America trust Bowline for dependable cross-border service that eliminates delays and surprises.

Bowline’s expansive network of carriers and support staff ensures that your goods get where they need to go, whether that’s a warehouse in Ontario or a distributor in California. When shipping solutions require both reach and regulation, Bowline’s got you covered.

Transportation Solutions to Meet Every Shipping Need

Bowline’s full-service model provides scalable transportation solutions to support every leg of your supply chain. Whether you need shipping services, warehousing, or third-party logistics, Bowline has the experience and infrastructure to handle it.

Here’s what Bowline offers:

  • FTL and LTL freight shipping
  • Cross-country and cross-border deliveries
  • Local and long-haul trucking across Canada
  • Intermodal freight coordination
  • Strategic freight shipping and specialized equipment transport
  • Inventory staging, warehousing, and real-time tracking

Every solution is built with performance and partnership in mind.

Supply Chain Expertise

A reliable transport company doesn’t just move goods, it strengthens your entire supply chain. Bowline understands how transportation decisions affect warehousing, retail, and end-customer experience. That’s why they provide actionable insights, proactive updates, and smart planning that reduce friction and improve outcomes.

Their tools offer strong functionality, giving customers shipment visibility, real-time ETAs, and responsive support, all working together to provide complete logistics solutions that perform under pressure.

Scalable Freight Solutions

Bowline serves businesses of every size, from small startups to national distributors. As a Canadian-based logistics company, they’re uniquely positioned to help businesses scale across the country—and into North America—with smart, efficient, and cost-effective freight solutions.

Whether you’re launching a new product or expanding your market reach, Bowline adapts with you. No guesswork. No growing pains. Just flexible transportation services and a partner you can trust to understand your company name and brand goals.

Driving Customer Satisfaction and Repeat Business

Bowline has earned a reputation for on-time delivery, transparent pricing, and unwavering reliability. Their commitment to customer satisfaction shows in their retention, many of their clients have been with them for years.

Because Bowline isn’t just fulfilling your shipping needs, they’re helping you deliver on promises to your own customers. That level of responsibility requires more than just trucks and drivers. It demands consistency, communication, and a company culture built on reliability.

When Reliability Matters Most, Businesses Choose Bowline Logistics

The transportation industry is crowded, but Bowline stands out because they show up. They deliver. They adapt. And they care.

When you choose Bowline Logistics, you’re choosing a trusted, reliable trucking company that’s as invested in your business as you are. Whether you need cross-border support, long-haul coverage, or flexible logistics services, Bowline delivers the partnership, performance, and peace of mind to keep you moving forward.

So if you’re looking for a dependable transport company with real reach, real relationships, and real results, you’re in the right place.

Bowline Logistics. When reliability matters most.

About the Author

Tyler Boyd – President

Tyler Boyd - President and CEO Bowline Logistics

Tyler Boyd is the President of Bowline Logistics Ltd., bringing over 15 years of hands-on experience in transportation, project logistics, and heavy haul coordination. Known for his operational leadership and commitment to service, Tyler grew up in the industry and now leads a fast-growing logistics company serving Western Canada and beyond.

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Started From The Bottom: How Bowline’s President Got Back In The Driver’s Seat

When you meet Tyler Boyd, President of Bowline Logistics, it’s easy to see the success: nearly 80 employees, 40+ trucks across North America, and a company known for reliability when it matters most. But what you don’t see is the storm he drove through to get here.

In a recent interview on the Business is fcking hard podcast, Tyler opened up about the lowest chapter of his entrepreneurial journey—and how he turned it into the foundation for everything Bowline stands for today.

“Bad things happen to good people. That’s one thing I learned. And I learned that the hard way.” – Tyler Boyd

The Day the Bank Pulled the Plug

Tyler’s journey didn’t start with Bowline—it began at age 12 with an agricultural business. By his 20s, he was running a thriving excavation company with over 100 employees. Then one email changed everything.

With less than an hour’s notice, his bank shut down his line of credit. Payroll was due. Bills were mounting. And the phones weren’t ringing.

Instead of folding, Tyler fought back. He let people go. Faced angry suppliers. Received public judgment. But most of all, he endured. The result? Not only did Bowline take shape during that time—Boyd Excavating, the business that started it all, continues to operate to this day. With a fleet of 40 trucks running alongside Bowline’s logistics operations, it stands as a testament to Tyler’s grit, loyalty, and refusal to let hard times define the outcome.

Rebuilding From Nothing

With no credit and very few resources, Tyler launched Bowline Logistics from scratch. He leaned into relationships and those who still believed in him, especially his family and wife, Amanda.

“My family’s day doesn’t start until Tyler comes home. That’s our whole purpose of the day—just to wait for him to come home.” – Amanda Boyd

That quote reflects a shift not just in priorities, but in philosophy. And so Tyler set forth to build that trust again, mile by mile. Today, Bowline is built on people. Trust, loyalty, and community are at the core of every haul, every hire, and every handshake.

The Lessons That Drive Him

  1. Failure is Just a Chapter – Tyler’s story proves that rock bottom isn’t the end of the road—it’s a detour, sometimes the one that leads you to something better.

  2. Business Is About People, Not Just Profit – From supportive competitors to unwavering family, relationships paved Tyler’s comeback. And they continue to steer Bowline’s direction.

Watch the Full Interview

Tyler shares more about the emotional weight of failure, the responsibility of leadership, and how he mentors entrepreneurs who feel like they’ve hit a wall.

Here’s a clip of Tyler’s story:

Watch the full interview here:

ABOUT THE AUTHOR

Michelle Green – Project Sales & Business Development

Michelle Green, Project Sales and Business Development - Bowline Logistics

Michelle is known for her deep industry knowledge, customer-first approach, and creative problem-solving in complex logistics environments. With a background in fluid power technology and commercial diving, Michelle brings a hands-on mindset and technical edge to every project. Whether coordinating time-sensitive freight or supporting large-scale industrial moves, she plays a vital role in building trust with clients and driving growth across North America.

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