When you live in a place that gets chilly, wet, and often snowy winters, you learn to not let a little bit of poor weather slow you down—especially if you lead an active lifestyle and love exploring the outdoors!

In fact, some truly dedicated hikers claim winter is actually the best season for hiking, thanks to that crisp, refreshing air and snow-covered landscape.

We’re not sure we’d go that far. But all said, we do encourage our patients who love hiking to keep up with their hobby all year long, provided they take some appropriate precautions to protect their feet and themselves.

And they have tons of great hikes to choose from, even here on Long Island! Let’s look at some great places to do some winter exploration—and then fill you in on some helpful hiking tips.

Top Long Island Winter Hikes

Here are a few of our favorites.

The North Fork

The North Fork is, of course, known for its wineries and vineyards—more than 30 of them, in fact, since the first opened less than 50 years ago—as well as its beaches. Not surprisingly, the region’s tourist spots tend to be packed during the late summer and early fall.

But even in wintertime, there’s still lots to do for an intrepid adventurer. Plus, no lines!

Inlet Pond County Park, just outside Greenport, is a good choice if you’re just looking for an hour or two of nature to pair with some shopping and wine tasting! There’s about two miles of easy trails here, and they’re well marked, so it won’t take you long if you plow straight through. But it’s fun to take your time and enjoy the secluded woods, as well as lovely views of both Inlet Pond itself and the Long Island Sound.

Then, of course, when you’ve had your fill of nature, you can cruise the quaint shops and museums of Greenport, stop in for a bite at one of its quaint, artisanal restaurants, and finish your trip at Kontokosta Winery.

Shelter Island

If, however, you’re looking for a true nature hike, Mashomack Preserve on Shelter Island can’t be recommended highly enough. There’s a reason they call it the “Jewel of the Peaconic.”

Starting from the visitor center, you can plan out your route and choose one of five marked trail loops ranging from 1 mile to 10 miles in length. (The shortest trail is fully wheelchair-accessible, too!)

All the while, you’ll enjoy a variety of landscapes to explore, including woodlands, salt marshes, freshwater wetlands, tidal creeks, and meadows. You’ll also no doubt spot many birds, and maybe even a fox or two. In winter, the trails do close by 4 p.m., so make sure you get there early to make the most of your day.

Before you take the ferry back to the mainland, though, be sure to stop in for some local cuisine. Vine Street Café is just a short distance from the preserve and offers delicious steak, seafood, and risotto dishes in a charming space. But there are many other options available for any taste or budget, particularly along Ferry Road.


But let’s say you don’t want to drive all the way out to the tail end of Long Island to go on your adventure. Is there anything closer that we could recommend?

Indeed there is. Smithtown is the home base for a couple of routes definitely worth investigating!

One is Blydenburgh County Park. The Stump Pond loop offers about 5 miles of mostly flat land around the namesake pond, complete with lovely views of the water and a great boardwalk section through the woods. It’s also pet-friendly, so take the doggo if you wish. You might even pass a few travelers on horseback!

Immediately adjacent to Blydenburgh, you can find Caleb Smith State Park Preserve. Less traveled and more contemplative, there are a variety of interconnected trails to explore. Again, gorgeous water views (complete with ducks and swans) are the norm here. Nature programs for both kids and adults are also offered multiple times per week—yes, even in winter!

Want even more suggestions? A while back we wrote a popular blog on running trails in Nassau County, and many of these suggestions also work for winter hikes, too!

Preparing Your Feet for a Long Walk in the Cold

So now that we’ve hopefully gotten you excited about some of the winter hiking possibilities, here are a few important tips to help keep you safe and comfortable!

Dress Your Feet Properly

For sure, you want a dedicated pair of winter hiking boots to protect you from the elements—including those around and under your feet.

What makes a good pair of winter hiking boots? You should look for:

  • Great grip. You really don’t want your foot to slip in icy conditions. Thick rubber soles with good treads are a must, or at least they should be compatible with microspikes or other traction aids.
  • Ankle support and protection. For winter hiking, you should opt for mid-to-high ankle cuts. This not only gives you extra protection against rain and snow, but also helps stabilize your ankle if you slip and slide a bit.
  • Waterproof materials. In addition to rubber on the soles and lower portion of the boot, treated leather or waterproof synthetic materials make good choices for the uppers. You can consider using a waterproofing spray on your hiking boots, too. Just remember that such sprays need 1-2 days to set before reaching maximum effectiveness, may slightly stain, and won’t be quite as good as boots made from truly waterproof materials.
  • Appropriate insulation. Makes sure hiking boots are warm enough for the conditions. Single-layered insulation is typically fine if you’re hiking close to home, since mid-day temps usually stay out of single-digit territory and below here on Long Island.
  • Removable liners. This is more personal preference, but having the liners be removable will help you dry out your boots faster, and also keep them warm overnight if you’re backpacking.
  • Appropriate for the type of hiking you’ll be doing. Technical mountaineering or long hikes/backpacking will require a heavier duty boot than simply hitting the trail for an hour or two. (Most hikes on Long Island are pretty flat and easy, so you probably won’t have to worry about this unless you’re taking a vacation to the mountains.)
  • Comfortable fit. As with any footwear, comfort is extremely important. Without a proper fit, good cushioning and good arch support, you greatly increase your risk for injuries, blisters, and chronic pain.
  • Space for orthotics. Absolutely essential if you already wear orthotics with your other shoes. Your need for proper arch support and foot alignment doesn’t go away when on a hike.

Once you’ve settled on a good pair of boots, don’t forget about socks! They can be just as important as boots in terms of keeping your feet dry, comfortable, and free from blisters.

Choose breathable, moisture-wicking fabrics to keep your feet dry during your hike. If you need a little more warmth, you can layer a thicker sock overtop it. Just remember to consider the overall combined thickness of your socks when shopping for hiking boots, as it will affect the fit.

Other Important Tips

Now, we’ve focused a lot on footwear here—as you might expect, given our profession! However, they obviously aren’t the only part of your body you should consider before heading out for a winter trek across a beautiful Long Island trail.

Some other quick tips to keep in mind:

  • Tell someone about your plans. Make sure someone not on the hike with you knows where you are going to be and when you plan to return, in case something goes wrong.
  • Bring a friend. This is good advice in any situation, but especially important if you plan to be out a long time and/or are generally inexperienced with winter hiking.
  • Check the forecast. This will tell you the best time of day to hike, or whether you should really be hiking at all. You want to get back to someplace warm before the temps start to really drop.
  • Dress the rest of your body appropriately. This will depend, of course, on the actual outdoor temperature—40 degrees is very different from 5! In general, you should dress in layers. The inner layer should be something that wicks away moisture and perspiration, while the outer layer blocks wind and moisture. Middle layers are for insulation. Wear a hat (you lose a ton of heat through the top of your head) and cover any skin exposed to sub-freezing temps (gloves, neck gaiter, etc.)
  • Bring eyewear. Sunglasses will be appreciated on a sunny day with a lot of snow cover. And if it’s especially cold or windy, a pair of goggles can make a huge difference.
  • Pack high-protein snacks that are easy to eat on the move. The extra protein is important since your body needs extra energy just to keep you warm, in addition to powering the hike itself. And you want something you can eat easily without stopping, so you don’t stand around and freeze! Also, one tip: foods like nuts, cheese, and chocolate generally do a better job of staying relatively soft even in very cold temperatures.
  • Bring a warm drink. Some tea or hot chocolate in a thermos is an exceptional idea if you plan to be out on the trail for a while.
  • Bring a way to contact others. Mobile phone batteries can die quickly in extreme cold temperatures, so a portable charger is also recommended.
  • Don’t be a hero. If conditions are truly awful—negative wind chills, high winds, blizzard conditions, rapidly dropping temperatures you aren’t dressed for, treacherous ice—turn around or just don’t go out. Find some exercises you can do at home instead and wait for a better day.

One last thing: If you find that you’re having trouble getting a comfortable pair of boots, dealing with constant pain or blisters from your hikes, or are suffering through a nagging chronic pain that’s keeping you from enjoying your outdoor activities this winter, give us a call!

Foot pain is best addressed as early as possible. That way, you suffer less and conservative therapies are more likely to deliver the relief you need.

To schedule an appointment with us at our office in Massapequa, please call (516) 804-9038 today. You can also request an appointment online.

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