The first rule of cycling is always check the air in your tires. The second is expect a headwind. The last – and most often forgotten – is a 10 percent chance of rain actually means 100 percent, so bring a damn coat.

For those living anywhere but some tropical paradise, riding in fall predictably means cooler temps, a higher chance of precipitation, and more variability with Mother Nature. That’s certainly true out here in Wyoming, and it’s part of the fun — long rides become less predictable and more adventurous, provided you have the right gear to avoid downright heinous outings. Crisp morning temps mean that toes and fingers can freeze fast, daylight is limited so lights become absolutely necessary, and waterproof options will eventually pay dividends.

With all that in mind, I use the fall as an excuse to skip the long and hard time trial workouts and replace them with gravel rides to places I’ve never been. These outings keep me curious — and allow me to turn around when I can’t feel my toes anymore. Even when you know the thermometer says 45 degrees and you dress appropriately, the temp can easily drop 10 degrees in just an hour.

And yet, fall has become my favorite season to ride. Beautiful colors, less traffic and the enduring sense of adventure keep me coming back. If you’re like me and looking to keep riding for a few more months, put away the short sleeves and fingerless gloves, and replace them with some of the battle-tested items listed below.

Helmet

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POC Tectal Race Spin: I use the Tectal for nearly everything — grocery runs, flowy mountain bike trails, and every ride in the fall. The visor does a great job keeping rain out of your face, the construction is sturdy, and it comfortably fits a warm hat underneath without looking like a gaper.

Buy Now: $220

Hat

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Joob Superfine Merino Beanie: Lightweight and incredibly comfortable, this merino hat lives on my bike year round, tucked in with snacks and a repair kit. It’s great for crisp mornings or cool fall days, and because it’s wool, it’ll still keep you warm when it gets wet from rain or sweat, which often happens.

Buy Now: $36 $27

Front Light

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Specialized Flux 1250: Easy to mount under or adjacent to a Garmin or other nav device, the Flux has a long-lasting battery and a super bright beam which illuminates enough of the road in front of you to know what trouble you’re getting into. The new 1250 is my go-to light for both city and trail riding.

Buy Now: $125

Tail Light

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Garmin Varia RTL510: The Varia is the biggest advancement in bike lights in… maybe forever? A small and sleek device that provides visual and audible alerts of vehicles coming up from behind, visibility to cars for almost a mile and 15 hours of battery life. It’s great for all types of fall rides.

Buy Now: $200 $170

Bike Computer

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Garmin Edge 1030: Top of the line navigation with built in high-res maps, communication with nearby Garmin riders, bluetooth connectivity and a bevy of performance data at your fingertips. The 1030’s battery runs for 20 hours, so you’ll never be stranded on a ride without a route home.

Buy Now: $600 $438

Long Sleeve Jersey

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Velocio Thermal Long Sleeve: Warmer than most jerseys but still breathable and comfortable on-skin, the Thermal is a great mid-layer for freezing days or outer layer on cool and crisp rides. A water-resistant zippered pocket keeps electronics safe too.

Buy Now: $199

Base Layer

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POC Road Layer Jersey: Simple and stretchy, this layer goes on most of my rides. It fits easily under bib shorts and adds a good 5 to 10 degrees — enough to make otherwise-frosty rides more enjoyable.

Buy Now: $90 $63


Jacket

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Specialized Deflect Hybrid Jacket: Affordable and incredibly packable, the Deflect stows easily out of the way when not in use, while keeping you dry in a mist or light rain. If it’s raining hard you might consider a hardshell, but even on two- to three-hour rides this jacket offers plenty of water resistance to keep me dry.

Buy Now: $140 $84

Mitts

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Hestra Nimbus Mitt: Simple and convenient, the Nimbus works with any other glove, adding warmth and weather protection. It’s great for the first few miles of a ride and easy to stash when you warm up. I pair these with Hestra Bike Long SR gloves for a perfect 1-2 punch.

Buy Now: $40

Bike Shorts

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Velocio Foundation Shorts: A high-quality, affordable option, these shorts are lightweight and incredibly comfortable, making them a great base for a full cold-weather layering system.

Buy Now: $99

Tights

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Patagonia Mission Peak Tights: Designed for trail running, these cold-weather tights are perfect for cool days on the bike. A warm windbreaking material that wicks well, this spandex blend stretches easily to not slow pedaling but still provide a snug fit. The easy-to-use pockets are great for stashing snacks or a phone.

Buy Now: $119


Pants

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Specialized Demo Pro Pants: For wet or cooler rides on trails, a warm and burly pair of pants comes in handy. The Demo Pros have space for pads and armor, but they’re still tapered enough to stay out of the chain and generally get out of the way. Bonus points for being water repellant.

Buy Now: $130

Socks

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Velocio Winter Wool Socks: Warm without being too bulky in most cycling shoes, these wool socks from Velocio keep my toes toasty on long days out in the fall and spring.

Buy Now: $28

Shoes

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Giro Chamber II Shoe: Made primarily for mountain biking, this shoe can tackle a wide variety of rides, including wet and cold adventures. A comfortable fit, water-resistant upper and cleat-capable outsole make it an all-weather all-star.

Buy Now: $150

Booties

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POC Thermal Bootie: Constructed from a water-repellant stretch fabric to beat back bad weather, the Thermal is surprisingly warm and offers nice small touches, like reflective detailing.

Buy Now: $70


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