High Sierra Freewheel Wheeled Backpack Review

We purchased High Sierra's Freewheel Wheeled Backpack so our expert reviewer could thoroughly test and assess it. Keep reading for our full product review.

If you’re looking for something to hold your laptop and other essentials without the look or feel of a standard rolling bag, the High Sierra Freewheel rolling backpack might be worth considering. 

This sporty-looking bag is made from durable fabric and can comfortably fit 15-inch laptops or smaller. The bag holds everything from books and paperwork for the office to clothing and toiletries for an overnight trip. And it's convertible—you have the option to carry it on your back like a backpack or roll it on wheels.

Design: Rugged with some cool features

This bag is different from other rolling laptop bags we’ve tested in that it bears neither the shape of a standard brief nor the shape of the average carry-on suitcase. It looks like a sporty backpack on wheels.

In addition to the main compartment, which can stow items like books, folders, clothing, and toiletries, the bag has two front compartments with pockets to organize cords, small gadgets or notepads, a wallet and more. The padded “Cushion Zone” computer sleeve fits up to a 15-inch laptop and keeps your device in place and protected from the minor bumps that come with travel. 

There’s also what the manufacturer calls a “designated media pocket” with a cable port. It’s really just a small opening that you can slide a cable through, whether to connect your phone to a portable battery or to connect a pair of wired headphones to your phone stored in that compartment.

On the exterior, a roomy beverage holder is built into the left side and a key fob sits on the front of the bag, but we’re not sure how useful or attractive this is to users—who wants to hang their keys smack-dab on the front of their bag?

The zippers are compatible with personal suitcase locks, which we deem an important security feature on any bag. The hideaway telescoping handle securely locks at two heights, and it’s easily tucked and zipped away when not in use.

Comfort: Easy on the back and shoulders (for the most part)

Mesh padded backpack straps allowed us to carry the bag like a traditional backpack, but in doing so, we discovered that the bag isn’t as lightweight as it’s billed to be. And, of course, it will only get heavier once it's full.  

With added hardware like wheels and a handle, any rolling bag is going to be heavier than a regular non-rolling backpack, and that’s something to keep in mind if you intend to carry it on your back most of the time. 

Performance: Take this thing anywhere

Made from sturdy Duralite Ripstop material, the High Sierra Freewheel bag is water-resistant. We actually dumped water on it as part of our testing to ensure that it could handle more than just a mist, and the inside stayed dry. This is especially important if you’re transporting electronics or paperwork. 

When we didn’t want to use the straps, we could tuck them into a pocket near the top of the bag to avoid letting them drag on the floor as we rolled the bag. And as far as the wheels, they gave us no trouble. In fact, they were pretty easy to roll on all kinds of surfaces—even carpet.

Price: Easy on the wallet

The High Sierra Freewheel wheeled backpack retails for $74.99, but you can usually find it for less than that online. This makes it cheaper than virtually all of its competitors. 

That aside, we still consider it to be a pretty good deal for the versatility and overall value that it offers, even at retail price.

Competition: High Sierra Freewheel vs. Racini Waterproof Rolling Backpack

The High Sierra Freewheel is one of two similar rolling backpacks that we’ve tested. The other is the Racini Nylon Waterproof Rolling Backpack. Both are waterproof bags with a laptop pocket, though the Racini can hold up to a 16-inch device while the High Sierra can only hold a 15-inch computer or smaller. The Racini is also a bit more expensive at $89.99 MSRP. 

If you’re looking for a true rolling backpack, the Freewheel is definitely the option for you because it’s shaped more like a standard backpack. It has a more flexible shape, so it can expand if you need to store more and doesn’t take up as much space if you have less to pack. Plus, its wheels fair better on rugged surfaces and it’s a little bit cheaper (especially if you can find it at a discount, which is common).