These tips and equipment will keep you sitting pretty when the temps get ugly.

everything you need for a 500-mile winter motorcycle trip
Gear Patrol

Last December, I had a wild idea. Instead of renting a car or buying a train or plane ticket, why not ride a motorcycle home for the holidays?

Now, this notion might not be a big deal if I lived in Southern California, or if my family resided nearby. However, I’m in New York City, and my destination was Northern Virginia. We’re talking about a 540-mile round-trip journey, much of it on major highways, at the start of an East Coast winter. That’s not the kind of expedition one takes lightly, even during a relatively mild December — so I knew I had to get serious about gearing up.

Spoiler alert: I survived the ride. Here are five major things I learned along the way, plus a rundown of all the gear I used to keep from freezing to death on this little cold-weather adventure.

1. Layer Smart

As you probably know, layering is critical to keeping your core temperature up and your blood circulating out to your extremities. It’s even more important on a bike, because once you get rolling on the highway, 65-mph wind makes things feel a lot colder. So rock plenty of layers (I maxed out at five on my upper body, including my jacket’s liner), and keep additional ones easily accessible by stashing them near the top of your saddlebag or luggage.

Make sure you have the ability to ditch layers, as well. You’ll want to shed some if you find you’re over-bundled; otherwise you’ll start sweating, and then you’ll really be cold if the temps drop.

2. Get Creative

Our good friends at RevZilla will tell you that one of the best ways to stay warm is to don heated gear, and they’re probably right. I have not yet taken this step, nor have I ridden a bike with heated handgrips — but I did recognize that Gore-Tex gloves and boots might not be enough to cut it with all that highway wind.

So in addition to doubling up on socks and adding a liner under my gloves, I took a friend’s unorthodox advice and put some of those magic chemical handwarmers on the backs of my hands and the tops of my feet. That move just might have warded off frostbite.

I also got creative with some of my layers: who needs “motorcycle-specific” apparel when the mountain-spec gear you’ve already got does the same job just as well, if not better?

3. Follow the Sun

Speaking of the sun, I can’t stress enough how ideal it is to ride when that nuclear ball of light and heat is high in the sky. I was cruising along with nary a care in the world on the last weekend of 2019 — when, maybe a hundred miles from home, night fell.

In a matter of moments, it felt like the temperature had dropped 20 degrees. I was chilly AF — and the combo of darkness, fatigue and frosty fingers made the whole affair suddenly seem a lot more precarious. I buckled down and powered through, but not before making a permanent marker mental note to leave at least an hour earlier next time.

4. Respect the Weather

I’ve done this NYC-to-greater-D.C. ride a few times before in warmer weather, and one of my previous trips taught me a painful lesson that served me well this time around.

That spring, I brushed off a minor rain forecast. Of course, less than an hour in, down came the drops, forcing me to spend all day drying off and praying for the precipitation to cease at a coffee shop before completing the journey at about 11 p.m. as a frozen and shivering mess. During my trip last month, I left a day early to beat some Sunday morning showers — and happily rolled along under the clearest of Saturday skies.

5. When in Doubt, Overbike

During a recent gravel biking camp in Arizona, I learned a fun new term from some cycling industry friends: underbiked. Like undergunned, it describes a situation where your set of wheels isn’t quite up to the terrain you’re tackling. Extreme example: riding a banana-seat Huffy on Whistler’s single-track mountain bike trails.

On the flip side of that coin, for winter riding, your best bet is to be overbiked. My daily city ride is a beautiful black Bonneville T-100, but I realized for this trip it might help to have a moto with real storage capacity, highway-crushing displacement — and, you know, an actual windshield. So I lined up the majestic Indian Chieftain Elite you’ll see below. It was a total overbike move…and it was spectacular.

Kali Protectives Catalyst Helmet

everything you need for a 500-mile winter motorcycle trip

It took me far too long to realize highway riding is much more pleasant with a full-face helmet. This badass matte black one just happens to be super-comfortable, streamlined and stylish.

WileyX WX Hayden Sunglasses

everything you need for a 500-mile winter motorcycle trip

That little rock dropping off the back of a truck can turn into a bullet at 80 miles per hour. Good thing these tactical shades meet ANSI Z87.1 industrial standards for high-mass and high-velocity impact protection.

BlackStrap The Hood Balaclava Facemask

everything you need for a 500-mile winter motorcycle trip

Bandannas are cool and all, but winter demands a bit more coverage. BlackStrap’s breathable, moisture-wicking balaclavas feature a helmet-friendly fit that comes in equally handy on snowboarding trips.

Lululemon Metal Vent Tech Long Sleeve 2.0

everything you need for a 500-mile winter motorcycle trip

Lululemon’s combination of good looks and seamless comfort have pretty much ruined all other first layers for me.

Backcountry Timpanogos Tech Fleece Hoodie

everything you need for a 500-mile winter motorcycle trip

Timpanogos is the second-highest mountain in Utah’s Wasatch range. It’s also a damn good mid-layer piece featuring stretch fabric, handy thumbholes and a hood that could save your neck if you forget your balaclava.

Arc’teryx Cerium SL Jacket

everything you need for a 500-mile winter motorcycle trip

I take this jacket with me just about everywhere I go. It packs down to the size of a peanut butter jar, then expands to provide way more down-based warmth than you’d expect from such a minimalist garment.

AlpineStars Ray Canvas V2 Jacket

everything you need for a 500-mile winter motorcycle trip

The exact jacket I used on my ride, the AlpineStars Kinetic, is no longer available, but this one is pretty dang similar. Key features include Level 1 CE-certified BIO-Light shoulder and elbow protectors, plus a durable, water-repellent shell.

HotHands Hand Warmers

everything you need for a 500-mile winter motorcycle trip

Ten hours of warmth for less than a dollar a pair? Sign me up.

Pearl iZuMi Men’s Cyclone Gel Gloves

everything you need for a 500-mile winter motorcycle trip

These cycling gloves served as a perfect liner to my moto gloves. Bonus: the index finger works on touchscreens, like the one between the handlebars of the Chieftain.

Dainese Nembo Gore-Tex Gloves

everything you need for a 500-mile winter motorcycle trip

Thanks to Gore-Tex Grip technology, these gloves are water- and wind-resistant while also providing exceptional grasp of the handlebars. They boast knuckle protection and a gauntlet that will make you feel like a medieval knight — and shield you from harsh weather, of course.

Lululemon Keep the Heat Thermal Tight

everything you need for a 500-mile winter motorcycle trip

Sure, they’re designed for winter running. They just happen to be an excellent first-layer liner, too.

Dainese D-Explorer 2 Gore-Tex Pant

everything you need for a 500-mile winter motorcycle trip

Where to start with how much I love these pants? A Gore-Tex membrane, removable liner and zippered thigh vents mean they’re tough enough to ward off wind, rain and cold, yet can be streamlined for summer riding, too. They are so comfortable you’ll forget all about the Trixior inserts that could save your knees if things go awry, and there’s even a matching all-season jacket.

Darn Tough Hiker Boot Sock Cushion

everything you need for a 500-mile winter motorcycle trip

Darn Tough’s socks are unquestionably burly. What some people may not realize is that they are also super-comfortable. And in the case of these thicker ones, super-warm.

Darn Tough Vertex 1/4 Ultra-Light

everything you need for a 500-mile winter motorcycle trip

I threw an extra sock on top of the first one for just a bit more warmth, and once the sun set on the return ride, I was quite glad I did.

Vasque Clarion ’88 GTX Waterproof Hiking Boot

everything you need for a 500-mile winter motorcycle trip

I’ve been effusive in my praise of this boot in the past, asserting that its throwback tech is perfectly suited to many modern activities. Thanks largely to waterproof Gore-Tex, a grippy Vibram outsole and plenty of cushioning, you can add long-distance winter motorcycling to the list.

Indian Chieftain Elite

everything you need for a 500-mile winter motorcycle trip

Last fall, I raved about the 2019 Indian Chieftain Limited, which I also took on a 500-mile trip. This 2020 bike in the same family is even better. It has everything that bike does and more, including three features that came in especially handy: a more user-friendly touchscreen navigation system; life-saving antilock brakes; and the coup de grâce: booming 400-watt speakers integrated into the front fairing and rear saddlebags for a true surround sound experience. It’s a real mood booster when the weather — or the traffic — gets you down.

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