I Ordered a 2027 Chevy Silverado Custom Trail Boss for a Year of Testing: Here’s How I Specced It
Alright, gearheads, I finally did it. I put an order down on a 2027 Silverado Custom Trail Boss, and it will be our long-term test truck here at GT: Garage Talk® for a full year. Here’s what I got, how I specced it, what I skipped, and when we expect it to show up.
If you’ve followed our coverage for the past few weeks, this won’t come as a surprise. The 2027 Silverado is extremely hot right now. A lot of you are eagerly anticipating it, and a lot of you are already ready to hate on it because of choices Chevrolet made, like dropping the dipstick and leather interiors. Either way, one week behind the wheel isn’t enough for a truck this important. It deserves 52 weeks of scrutiny, so that’s exactly what we’re going to give it.
Why I Ordered a 2027 Silverado Custom Trail Boss
I started on Chevrolet.com with a crew cab short bed. These are going to be everywhere, especially here in Texas, where the crew cab pickup is basically the family sedan. I’ve already walked through the cheapest and most expensive builds in my 2027 Silverado pricing breakdown, so this time it’s all about the truck I actually ordered.
Next, I picked 4WD. My first brand-new vehicle, 20 years ago, was a 2007 Silverado. It was a 2WD Texas Edition with 20-inch wheels and the Eaton G80 automatic locking rear differential, and I thought I was invincible. I promptly got it stuck multiple times. Back then, I bought it for work cleaning swimming pools because I needed the bed. This time, I want the capability.
That’s why I landed on the Custom Trail Boss, a trim I already said I’d order with a V8 and a bench seat. It starts at $54,400 before destination and comes with a 2-inch lift with monotube shocks, 34-inch mud-terrain tires on 18-inch Dark Android aluminum wheels, skid plates, a two-speed transfer case, and red recovery hooks.
The Spec: The 5.7-Liter V8 and a Color That Costs Extra
The Custom Trail Boss offers the Duramax diesel, which I really love. However, the updated turbocharger on the Duramax puts it in late availability, so you’ll be waiting a while for one. Instead, I went with the new 5.7-liter V8.
The big news under the hood is two brand-new V8s, backed by an $888 million investment from General Motors in the plant producing the 350 and 400 cubic-inch engines. Chevy has told me on multiple occasions that the 5.7 will be the volume engine. It’s also the only engine offered with the Max Trailering Package across the Silverado lineup, and you can get it with 2WD or 4WD.
By comparison, the 6.6-liter V8 is only available on two configurations: the High Country with 4WD and the ZR2. The ZR2 uses the Duramax as its base engine, and the 5.7 is the base engine on the High Country. That’s very limited availability for the 400 cubic-inch engine. Maybe more of those blocks are headed to the Corvette, but I don’t know why there’s so little emphasis on it. For the full breakdown, see our 2027 Silverado engines by trim guide.
For paint, I had to get the new green. I love that green is back, and red is a little overdone. Red Hot is now fleet only, and a fleet-order Custom Trail Boss is late availability anyway. So naturally, I wanted the one paint color that costs extra ($395). Of course I did. I’m also sticking with the 18-inch wheels. You can get 20s, but don’t do that to me.
Six Seats and a Cabin That Finally Caught Up
There’s only one interior on the Custom Trail Boss: Jet Black cloth with a front bench and six-passenger seating. I actually want that. You can fit as many people in this four-door pickup as you can in many three-row SUVs. We have a crossover SUV in the driveway right now with seven seats, and let’s face it, you’re only getting six people in there.
That said, the middle front seat is for your shorter friends. There’s a transmission tunnel, and the controls sit down low. The seat bottom hides storage, and so does the seat back, so both are a little firm. You also sit up and out a bit more than the outboard passengers. It’s an emergency seat, but so is the middle seat in the third row of many three-row vehicles. Can you take six people? Yes. Will you? Probably not, but you can.
What I’m most excited about is the new dash. The current 2026 Trail Boss has an interior that dates back to the 2019 redesign. It has a very small screen, an old layout, and an old design, and it didn’t get the 2022 midcycle refresh that the higher trims received. Now we get a full digital driver display and a 16-plus-inch touchscreen with more screen real estate, more capability, and phone projection.
My 5-foot wife is really going to love the A-pillar grab handles on both sides, too. She won’t have to pull on the steering wheel to get in. Every 4WD truck gets transfer case controls, every truck gets trailer brake controls, and there are USB ports, a secondary glove box, and no passenger screen. I appreciate that a lot.
Inside, I added the wrapped steering wheel ($225). Notice I didn’t say leather wrapped. There’s no leather in the 2027 half-ton; it’s all EvoTex. I’ve sat in those seats, and they’re comfortable and very soft, with a slightly smoother feel than the grain on other synthetic leathers. Engineered materials are claimed to be lighter and more durable than cowhide. Less weight saves you fuel over time, though that isn’t to say the engineers didn’t use that weight somewhere else.
The wrapped wheel requires the $970 Assisted Driving Package, which also adds heat to the wheel. In other words, you can’t get it wrapped without getting it heated, so why they’re separate on the order sheet, I don’t know. The package also brings exterior perimeter lighting on the mirrors, Surround Vision (360-degree cameras), traffic sign recognition, and an interior camera. I covered that interior camera in our 2027 Chevy Traverse story.
The Options I Checked, and the Ones I Skipped
This is the page where I learned things I didn’t know when I placed the order. They weren’t clear from the order guide or from my conversations with my dealer.
I did add the $765 Protection Package. It brings rear wheelhouse liners and a spray-on bedliner. The red dirt around here ain’t no joke, y’all, so I want that protection. You can get a drop-in bedliner for about half the price, but I’m not sure why you would.
On the other hand, I skipped the bed covers, steps, and utility wall package. Just because the brand offers it doesn’t mean it’s the best option for you. I’m looking to partner with aftermarket brands so I can show you different offerings from across the industry. You’d think a 2-inch lifted truck and a 5-foot wife would mean steps from day one. Instead, we’ll add steps later and find a better option.
Two Packages I Didn’t Know About
First, there’s a $3,299 Rally Package. It adds black rally hood stripes and 18-inch multispoke gloss black painted aluminum wheels described as beadlocks. In the product image, they don’t look like beadlocks, so I’m not sure why it says that. Either way, that’s $3,299 for wheels and hood stripes, all of which can be added afterward. I passed, and I prefer the base hood without the stripes anyway.
Second, the $5,345 Off-Road Package brings off-road A-pillar lights, rocker protection, those 18-inch wheels, and touchscreen control switches for auxiliary accessories. The switches use 60 amps to run up to six external accessories, and the illustration is clearly a Colorado. The package image also shows the Trail Boss hood applique, which my truck doesn’t get. I like the A-pillar lights, but I’ll potentially add those later from an off-road manufacturer.
Steps, Switches, and the Price of Digital Buttons
I really don’t like the removable steps. They’re going to get hung up on something off-road. To add them (about $1,300), Chevy also makes you get the $1,500 rocker protection, for $2,845 combined. If I were buying steps from the brand, I’d pick the off-road high-clearance steps instead. So no, thank you.
Then there’s the standalone accessory touchscreen control switch option for $900. You’re paying $900 for digital buttons. Let that sink in. I know there’s hardware involved that makes adding accessories easier. Still, the aftermarket can do this, and you’d get physical switches instead of digging through a screen. I’m not paying nearly $1,000 for digital buttons.
What Our Long-Term Silverado Costs
Here’s how my truck adds up. It starts at $54,400, and the options include the $400 paint, the $225 wrapped wheel, the $970 Assisted Driving Package, the $765 Protection Package, and the V8. After a destination charge of nearly $3,000, my 2027 Silverado Custom Trail Boss comes to $62,015.
That destination charge stings. This truck will most likely be built in Mexico, and it costs nearly $3,000 to get it here via planes, trains, and automobiles. I remember when $1,200 was ridiculous. We’ve more than doubled that.
What’s Next for Our 2027 Silverado
We expect the truck to arrive later this year, and I’m already drooling. Once it’s here, I plan to compare it to every truck I can get my hands on locally. That includes the rest of the Chevy lineup, every GMC, and every Ford, Ram, and Toyota Tundra. The 2027 Tundra Trailhunter on the SR5 is very comparable to this truck, but I believe it will cost more, and you don’t get a V8.
We’ll also test a lot of aftermarket accessories. So tell me in the comments: what accessories do you want to see on this truck, and what do you want us to test? If they fit our needs and our lifestyle, I’ll try them.
There will be an entire YouTube playlist dedicated to this truck as we buy options, add accessories, test it, and compare it. Subscribe and ring the bell so you don’t miss an update. You can also find us at @GTGarageTalk on every social platform, and you can sign up for our weekly newsletter right here on GTGarageTalk.com. Until next time, gearheads.