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How To Enjoy Winter (Even If You Hate It)

Many people have a favorite season. Some prefer the hot, long summer days, while others enjoy the cool, crisp air of autumn or spring. Not many people love winter, but I have grown to become one of them over the last decade. It wasn't easy, and it took a lot of patience, time, and a shift in mindset to cultivate my love for winter.

If you have not been fond of the cold season in the past, in this blog post, I’m sharing a few easy ways to enjoy winter without feeling miserable.

Getting Through Winter

Depending on where you live, winters can be mild or fierce, long or short. Here in Boston, it is DARK. The average winter daylight here is only 7 hours; it feels like the darkness never lifts on gloomy days.

I struggle with that and come to the end of January, I am usually desperate for signs of spring. So, I need small, easy things to help me get through winter more easily and cheerfully.

My best advice - don't stay indoors all winter. I know it's cold outside, but avoiding daylight and fresh air won't make you feel good.  Of course, there will be wet, windy days when you won't go out, and that's okay.

But only stay in for a few days. 

My mental health takes a real dive when I don't get outside for a while, so I make it a priority to get out most days, even if it's just for a short time. Sometimes, I have to force myself, but I never regret it.

So go outside for a walk, boost your mental health, and get your vitamin D. Remember to wrap up warm, or you'll be miserable. 

This leads me to the next point…

Although I love the quote by Alfred Wainwright, "There's no such thing as bad weather, only unsuitable clothing," we all know that bad weather does exist. Today, as I look out the window, I see a frigid and gray day.

However, the point of his quote is that if you don't invest in the right clothes, you'll always hate winter. Proper and practical clothing is crucial to staying warm and comfortable in cold weather.

During my twenties, I used to wear impractical clothing in winter. I never owned any weatherproof clothing or warm and sensible footwear. However, my experience with frigid temperatures in Ithaca, New York, taught me the importance of dressing appropriately for the weather. Now, I love all things cozy, warm and waterproof.

After learning about proper winter clothing, my perspective on the season changed significantly.

Let's take a moment to review your winter gear and ensure you have everything you need to stay comfortable and safe during the colder months. This is the perfect time to declutter and eliminate any items that no longer serve you. By preparing yourself with the proper clothing and gear; you can make the most of your outdoor adventures and create some wonderful winter memories with your loved ones.

Here's a quick list of essential items that you should have for winter:

1. Base Layers: It's important to wear a warm layer close to your skin to keep yourself warm during winter. Fleece-lined thermals work best on frigid days. Wearing thermals throughout the winter is a great way to avoid feeling cold.

2. Socks: It's best to put away your cotton socks during winter. Your toes will be much happier in wool socks, preferably thick hiking ones or the lovely Scandinavian-style Nordic socks that I can't get enough of.

3. An insulated waterproof coat: Invest in the best coat you can afford, and you'll be able to wear it for years. 4. Hats, Gloves, and Warm Scarves: Go for wool or fleece, and ensure they're soft enough so you don't want to pull them off. For gloves, insulated ones with a waterproof layer are the best choice.

You can make your outdoor experience more comfortable by referring to our comprehensive list WINTER CABIN PACKING LIST (FOR A COZY GETAWAY)


Sometimes, enjoying winter outdoors in New England can be intimidating without being a winter sports enthusiast or owning expensive gear. However, many ways exist to enjoy the winter outdoors without skiing or driving far for hiking spots.

You can just go outside.

When Lennon was a baby, I started taking an evening walk daily. My body instinctively knew I needed to ensure I still spent time outside, even with a tiny baby. Although an evening walk isn't revolutionary, it was the game-changer for me to go on this walk every night, regardless of the weather.

Norwegians say there's no such thing as bad weather, just bad clothing, and it's true! If you wear enough wool underlayers and a waterproof jacket, you can go outside in (almost) any weather and stay toasty and dry.

There's something so freeing about that. Once I realized I could enjoy walking in sideways rain and sleet, I no longer felt locked inside by bad weather, which made stormy days feel much less gloomy.

While sometimes I still have to psych myself up for going outside in terrible weather, I usually enjoy those walks the most because something is energizing about walking through a storm.


If you're looking for ways to enjoy the outdoors while still coping with the weather, plenty of activities can help you have fun. There are various outdoor events and festivals that you can attend to enjoy the fresh air and socialize with others. Whatever you choose, dress appropriately for the weather and stay safe.

6 Ways To Enjoy The Outdoors In The Winter

1. Enjoy a Bonfire or Firepit

When I think of bonfires, I think of warm summer evenings spent with loved ones, gathered around the flickering flames, roasting marshmallows, and enjoying each other's company. 

However, during the summer months, there is often a risk of forest fires, which means that open flames are prohibited in many areas. But, when winter comes, the ground is covered in a thick layer of flame-resistant snow, making it the perfect time to enjoy an outdoor bonfire.

New England is a fantastic area for hiking and skiing enthusiasts, as we know. What I love about this region is the abundance of hiking and skiing spots equipped with fire pits. Even if you're not into skiing, many ski resorts offer a variety of amenities, such as breweries and restaurants.

The fire pits in these spots are a great place to take a break, warm up, and enjoy the winter scenery with your loved ones. There's nothing quite like cozying up by the fire, taking in the stunning winter landscape, and enjoying its warmth and camaraderie. Whether you're looking for cocktails and bites or are feeling adventurous and decided to ski or snowshoe, take advantage of these fire pits.

2. Dine in an Igloo or Gondola

The trend of outdoor dining experiences in the form of igloos, yurts, greenhouses, and even Hobbit Houses has become increasingly popular. Initially introduced as a socially distant dining option during the pandemic, it has continued to thrive as an alternative for diners who prefer to eat outside.

This chic retreat has become quite popular on social media due to its unique features. While searching, we found many vintage ski gondolas furnished with warm woods, heated blankets, mini electric heaters, cozy seating, and fine Alpine textiles.

Additionally, there are plenty of opportunities for Insta-worthy moments around the fire pits. Some may even argue that dining here is more enjoyable than traditional indoor dining.


Igloo and Gondola Dining Experiences Around New England:

For unique experiences near Boston, check out these amazing spaces:

  • Lookout Roof Top - While at Lookout's igloos, you'll be able to enjoy the stunning views of the Boston skyline while enjoying the limited seasonal menu

  • Bow Market (located in Somerville, MA) Cozy fire pits have been installed in the central courtyard for people to relax and enjoy food and drink from nearby stalls.

  • Woods Hill at Pier 4 (Boston, MA) offers an exceptional dining experience with nine stunning igloos along the waterfront. These igloos provide an ideal setting for outdoor dining without any concern for the freezing temperatures and snow.

3. Attend a Winter Market

Plan a fun day with your friends and check out a few outdoor winter markets! Many cities and towns hold beautiful outdoor markets during the winter season.

Local artisans sell unique handmade goods and delicious specialty foods. These markets are great places to purchase Valentine's Day gifts! 

4. Take Family Photos

Many families opt for professional photos during summer and fall, but why not consider winter as your photo backdrop? The snow-covered trees can create enchanting scenery, and you can also use the images for next year's Christmas card.

Are you based in New England and need to schedule a photoshoot? Look no further than Katie Kelley! We recently had the pleasure of chatting with Katie about her passion for photography and her love for the natural beauty and charming small shops of New England's coastlines. You can check out our insightful conversation with Katie here.

5. Take a Road Trip

Whenever we want to leave the house for a few hours, we like to take a mini road trip and enjoy New England's many scenic drives. Backroads through Massachusetts and New Hampshire offer a peaceful escape amidst stunning landscapes and is one of our favorite drives. If you bring snacks, a thermos of hot chocolate, and a blanket, you can keep warm and cozy in the car. 

One of our favorite destinations in Littleton, NH, just a mere 2.5-hour drive from Boston, offering an idyllic small-town experience. Main Street has several antique shops, including Just L and the Shaun Terhune Gallery, which features stunning White Mountain landscapes and wildlife photography.

You'll come across various restaurants in the area, including the Schilling Beer Co. This spot boasts incredible views of the Ammonoosuc River and offers wood-fired pizzas and a range of artisan beers. You can dine inside or outside in the cozy wood-framed huts surrounded by heating lamps and several fire pits to keep you warm and toasty.

Escape from your routine and treat yourself to an enchanting winter weekend getaway in the serene landscapes of New Hampshire. Our blog is the ultimate guide for planning your perfect vacation. Check it out now, and get ready to embark on an unforgettable journey!

6. Try something new 

Many Audubon sanctuaries offer opportunities for the local community to explore local areas and to connect people with nature. Check with your local nature reserve for beginner classes in snowshoeing, cross-country skiing, and other outdoor activities.

Nature lovers in the Boston area can enjoy various activities organized by Trustees and Massachusetts Audubon. These activities include maple tree tapping (shown on left), snowshoe hikes, cross-country skiing, birdwatching, photography lessons, evening hikes, horse carriage rides, sledding hills, and fire pits.

Check out their website for more information. 


Reflecting on my childhood, some of my happiest memories were playing in the snow. Coming home with pink and mostly numb cheeks was a sure sign that I had a great day. I enjoyed all sorts of winter activities that got me out of the house and made the most of an otherwise gloomy season. 

Approaching the winter season with a positive mindset, appropriate clothing, and a willingness to try new activities can help you make the most out of this season.

Looking for more winter resources?

I genuinely believe the winter season can be as great as all the others when you know how to embrace it properly. For more winter resources, refer to this section on the blog!

And if you’re looking for help planning your next winter getaway, we’d love to help. 



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