2020 Chevy Silverado Trail Boss Midnight Edition Review

Life in the city with the all-black monster, plus a look at 2021 Silverado upgrades.

Full-size pickups remain the biggest-selling vehicles in North America and sales have held up well during the Covid-19 pandemic. The Chevrolet Silverado, in particular, almost matched 2019 volumes in the USA for the first nine months of 2020, as it continues to chase the market-leading Ford F-150.

With a new F-150 on the way in 2021, the Silverado is being upgraded to maintain its challenge. We recently spent time with a 2020 Silverado Trail Boss Crew Cab Midnight Edition to assess the current state of play. We’ll take a look at that vehicle in this review and highlight some of the biggest changes for the 2021 model.

2021 Chevrolet Silverado pricing

There’s seemingly a Silverado for every need and every budget (like this 2021 Realtree Edition and 2021 HD Carhartt Special Edition), but we’ll narrow the field a little by sticking to Crew Cab versions here. They range from the basic, short-bed WT with 2WD at C$38,698 / US$36,110 (MSRP) to the standard-bed, 6.2-litre, 4WD High Country at C$70,393 / US$61,290.

Our test truck was an LT Trail Boss 4WD with an MSRP of C$56,098 / US$52,495, but it came loaded with extras and upgrades, including the 6.2-litre motor (an extra C$2,895 / US$2,495) and Midnight Edition package (C$1,225 / US$1,070), that took the final sticker price to C$72,738 before taxes and charges.

Silverado Trail Boss exterior styling

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2020 Chevy Silverado Trail Boss Midnight Edition. Photo: Amee Reehal

The Trail Boss Midnight Edition is a huge, high-riding, mean-looking truck. The standard Z71 off-road equipment beefs things up with skid plates for the engine oil pan and transfer case, and dual exhaust pipes.

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The Trail Boss trim adds a 2in suspension lift, magnifying the pickup’s imposing presence. Our vehicle had 18in rims but 20in black wheels with Goodyear Territory MT tires are available on 2021 models.

In addition to the standard black paint, the Midnight Edition package specifies LED reflector headlamps with dark bezels, black exhaust tips and badging, and protection for the bed and rear wheelhouse liners.

Silverado Trail Boss interior and equipment

A C$1,325 (US$995) power sunroof and C$995 (US$760) leather seating package were the notable cost-options fitted to the interior of our Trail Boss. Both felt like must-have features for comparatively little extra money.

The practical touches are what the Silverado’s cabin does best. Driving in cold conditions, the chunky switches were easy to operate with gloved fingers and the flip-up rear bench is handy for loading everyday cargo that you might not want to put in the bed, such as groceries.

2020 Chevy Silverado Trail Boss Midnight Edition interior
2020 Chevy Silverado Trail Boss Midnight Edition. Photo: Amee Reehal

Overall, we liked the upscale work-truck feel of this Silverado, but the interior design lacks the imagination and premium touches of the Ram 1500’s cabin. The column-shift feels old-school and the 8in screen seems unworthy of a C$70k vehicle – again, FCA sets the pace here.

A notable infotainment upgrade for 2021 is the addition of wireless phone projection through Apple CarPlay and Android Auto: standard on LTZ and High Country models but also available on LT, LT Trail Boss and RST.

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Also worthy of note is the new multi-flex tailgate that’s coming to all Silverados from early-2021. It can split the existing tailgate into two tiers to provide six different functions, including to create a standing workstation or to ease access to cargo in the bed.

Silverado towing and trailering

Our Trail Boss came with the optional trailer camera package (C$410) and the advanced trailering package (C$550/US$490). The former uses three cameras to provide a 270° view when backing up, while the latter has features that automatically apply the parking brake when you’ve lined up to the trailer, provide a dynamic backing guideline to help line up the hitch via the camera system and monitor the trailer’s tire pressures. Towing capacity in this spec is 9,200 lb (4,218kg).

Away from the test truck’s 6.2-litre V8, Chevrolet has increased the towing capacity for two of the Silverado’s smaller engines for the 2021 model year after further testing. All configurations with the 2.7-litre turbo or 3.0-litre Duramax turbodiesel – which gets a US$1,500 price cut in the US – are now rated to at least 9,000 lb (4,082kg).

Chevy notes that both of these engines now meet or exceed most trailering needs, as 96% of light-duty pickup owners tow less than 10,000 lb, according to data from InMoment. 

Chevrolet Silverado Trail Boss driving impressions

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2020 Chevy Silverado Trail Boss Midnight Edition. Photo: Amee Reehal

We drove the Trail Boss exclusively around town and on the highway, which is not the environment for which it is designed but does represent where many of the trucks will spend most of their time. We found that the extreme ride height – we regularly looked down on other pickups – makes it hard to place the truck when parking or maneuvering at low speeds.

The ride is good on Rancho off-road monotube shocks and Goodyear Wrangler DuraTrac tires, but snowy conditions were a reminder that 4WD and MTs are still no substitute for proper winter tires in cold weather.

The 10-speed auto works well to keep the 460 lb-ft., 420-HP V8 humming efficiently. Like the 5.3, this latest EcoTec3 motor can shut down up to six of its eight cylinders when not required thanks to the Dynamic Fuel Management system. It works well in practice: you occasionally feel a slight lumpiness at low loads, but I’ll take that every time as the price of fuel savings. Official combined economy is 14.2L/100km (17mpg).

Takeaway: is the 2020 Chevy Silverado Trail Boss Midnight Edition worth it?

The Trail Boss isn’t best suited to city life, but we don’t doubt it would excel in the off-road environment for which it is designed, or when working or pulling a trailer. If your focus is on cabin style, we still prefer the Ram’s fresher approach.

In 2021, all Silverados will be harder pushed than ever to keep pace with the F-150, which will be available in a hybrid version for the first time. Chevy’s package of upgrades – especially the multi-flex tailgate and some crucial towing capacity increases – will help its cause.


  • Visual presence
  • 2021 multi-flex tailgate adds practicality
  • High-tech towing aids


  • Tough to use in the city
  • Ram does a better truck cabin
  • Stiff competition from new F-150

Exterior & interior pictures of the Silverado Trail Boss Midnight Edition:

Graham Heeps
Based in Calgary, AB, Graham’s outlets include Autocar, Professional Motorsport World, Turnology.com and Electric & Hybrid Vehicle Technology. A lifelong motorsports fan, he’s a member of the Automobile Journalists Association of Canada (AJAC), the Guild of Motoring Writers and the Motor Press Guild, speaks German and collects Matchbox cars (at the same time).