Winter Hiking in the Catskills: How to Stay Warm Without Overheating

October 23, 2025

Written by Jen

Here's the counterintuitive truth that every winter hiking veteran learns: staying warm isn't about wearing the warmest coat. It's about mastering the art of layering and managing your body temperature so you don't overheat.

The "Be Bold, Start Cold" Rule

If you're comfortable standing at the trailhead, you're wearing too much. This might sound crazy, but experienced winter hikers swear by the "Be Bold, Start Cold" motto. You should feel slightly chilly when you begin—within 10-15 minutes of hiking uphill, your body will generate plenty of heat.

The problem? If you start warm and cozy, you'll quickly overheat as you climb. You'll sweat. And sweat is the enemy in cold weather—once that moisture is against your skin, you'll get dangerously cold the moment you stop moving.

Skip the Heavy Coat—Layer Smart Instead

Before you invest in a warmer jacket, try this: add an extra base layer instead. Many experienced Catskills winter hikers stay comfortable in temperatures below 20°F wearing just a base layer and a fleece while moving. That's it.

Here's a proven layering system:

  • Base Layer (Next to Skin)

    This is your foundation. Merino wool or synthetic materials that wick moisture away from your body. In colder temps, consider a midweight or expedition-weight base layer. Never cotton—it holds moisture and will leave you freezing.

  • Mid Layer (Insulation)

    A fleece or lightweight synthetic insulated jacket. This traps warm air and continues wicking moisture outward. You might even skip this layer on steep climbs and just hike in your base layer.

  • Outer Layer (Shell)

    A windproof and waterproof shell jacket for protection against wind, snow, and precipitation. This stays in your pack until conditions demand it.

  • The Puffy (In Your Pack)

    Here's the key: keep a puffy jacket in your pack for breaks and summits. When you stop moving, your body temperature drops fast. That's when you throw on the insulated jacket, enjoy the view, snap some photos, then pack it away before you start moving again.

Down vs. Synthetic: What You Need to Know

Down fill power (like 700, 800, or 900) measures how much space one ounce of down occupies. Higher numbers mean more loft and warmth for less weight. But here's the catch for hiking: don't hike in real down.

Down loses all its insulating properties when wet, and you will sweat while hiking. Choose synthetic insulation (often called "synthetic down") for your active layer. It insulates even when damp and dries much faster. Save the premium down jacket for camp or stationary activities.

Don't Forget Your Extremities

You can have the perfect torso layering system, but if your head, hands, and feet are cold, you'll be miserable. These areas lose heat fast:

  • Head: A warm beanie or balaclava. You lose significant body heat through your head—cover it.

  • Hands: Start with liner gloves, carry insulated gloves or mittens for stops. Mittens are warmer than gloves but less dexterous.

  • Feet: Wool or synthetic hiking socks (never cotton), and insulated winter hiking boots if you're tackling snowy trails. Consider bringing an extra pair of socks in case the first pair gets damp.

Managing Temperature on the Trail

Winter hiking is a constant dance of adjusting layers:

  • Ascending: You'll heat up fast. Strip down to base layer and maybe fleece. Unzip vents. Take off your hat if you're overheating (though watch for wind chill).

  • Summit/Breaks: Stop moving for more than 2 minutes? Throw on that puffy immediately, before you start cooling down. Add your shell if it's windy.

  • Descending: You'll generate less heat going downhill. You might need to add a layer or two back on.

The goal is to maintain a steady body temperature—slightly cool to comfortable, but never sweating and never shivering.

Your Winter Hiking Gear Checklist

Before heading out on winter Catskills trails:

  • Moisture-wicking base layers (top and bottom)

  • Insulating mid-layer (fleece or light synthetic jacket)

  • Waterproof/windproof shell jacket and pants

  • Synthetic puffy jacket (for your pack)

  • Warm hat and gloves/mittens

  • Wool or synthetic socks

  • Winter hiking boots with good traction

  • Microspikes or crampons (essential for icy trails)

  • Extra layers in your pack

  • Hand warmers (backup for extreme cold)

  • Thermos with hot drink

That thin down jacket and fleece? They're probably fine—you just need to use them differently than you think. Hike in your base layer and fleece, pack the down (or better yet, a synthetic puffy), and pull it on only when you stop. Invest in better base layers and don't forget your extremities.

Winter in the Catskills is too beautiful to miss. Those snow-covered trails, ice-glazed waterfalls, and crystalline summit views are calling. With the right layering strategy, you'll stay comfortable from trailhead to summit and back—without spending a fortune on a warmer coat you don't actually need.

Now get out there. The winter trails are waiting, and they're spectacular.

Stay @ Entire Manor

Entire Manor

3 bedrooms, 4 beds (queen, double, 2 x twin), 1.5 baths, sleeps 6

Entire Barnhouse

Entire Barnhouse

3 bedrooms, 4 beds (queen, 3 x twin), 1 bath, sleeps 5

Manor + Barnhouse