How to Decorate a Vintage Sled, A Simple Styling Tip with New England Charm

There’s nothing quite like learning how to decorate a vintage sled or antique toboggan to capture that timeless ski lodge charm. These nostalgic pieces instantly transform a porch or entryway into a cozy white winter wonderland, telling a story of alpine adventures while adding warmth and character to your seasonal style.

I found this vintage toboggan during one of my regular thrifting drives between Vermont and Maine, at a beloved secondhand shop (now sadly closed). It was just $58, and with its worn wood, original rope, and classic shape, I knew it would be perfect for our Vintage Ski Lodge Decor theme.

I couldn’t wait to style it on our Vermont porch as part of my Styling Tip Series, where I share quick, creative vintage decorating ideas you can try at home, too.

Where to Find the Best Vintage Sleds to Decorate

If you’re planning to decorate a vintage sled this winter, the first step is knowing where to find one. Antique toboggans, wooden sleds, and jack jumpers often show up at local thrift shops, flea markets, estate sales, and antique barns, especially in New England towns where vintage ski lodge charm runs deep.

Keep an eye out during your seasonal thrifting adventures or weekend road trips. Online marketplaces like Etsy and eBay also offer a wide variety of options if you prefer to shop from home. From rustic to refined, there’s a vintage sled out there just waiting to be styled for the season.

While searching for ways to decorate a vintage sled, I spotted these beauties at antique stores across New England, each one full of charm and potential.

How to Decorate a Vintage Sled Toboggan for a Simple Winter Porch Style

When styling a large vintage sled like a wooden toboggan, you don’t need to overthink it. These nostalgic pieces make a statement all on their own. Leaning one against your porch, barn, garage, or even inside near a fireplace brings instant vintage ski lodge charm to any winter setting.

That’s exactly how I began styling this vintage toboggan I found while thrifting on a recent drive from Vermont to Maine. At first, I leaned it up against the cedar shake siding of our coastal Maine home, where it instantly brought a warm, nostalgic feel to our snowy porch. Later, I brought it back to Vermont and styled it again, this time against the red barn, where it looked just as charming nestled in the snow.

Simple, classic, and full of ski lodge spirit, this vintage toboggan adds timeless character no matter where it lands.

Decorate a Vintage Sled with Mittens, Evergreens & Vintage Charm

To add a personal touch, I clipped on a pair of handmade wool mittens I found at a summer music festival in Bangor, Maine. A little wire and some freshly cut evergreens made the perfect rustic accent. You can also tuck in pinecones, plaid scarves, or vintage skates for even more winter style.

I’m especially fond of the original Northland logo stamped across the top of the sled, a nostalgic nod to its mid-century roots, since Northland stopped producing sleds in the 1950s.

Right beside the sled, I placed our old Christmas tree in a stand, letting it live on as simple porch greenery through the winter months. It adds just the right amount of warmth and texture without feeling like leftover holiday decor. See more in my 7 Snowy Scenes That Define Vintage Ski House Decor post.

I also styled the space with a wicker tray table I found at a local antique shop. It will be perfect paired with our green rattan porch furniture come spring, but for now, it blends right in with our cozy winter porch look.

And of course, our Bernese Mountain Dog Ella, had to make her modeling debut, posing in front of the toboggan with a plaid scarf and blanket for a final touch of vintage charm.

Whether you’re decorating a vintage sled for the holidays or simply adding character to your winter porch, sometimes the simplest displays are the most magical.

Vintage Jack Jumper Sled Decor: How to Style This Vermont Classic

If you’re looking to decorate with a vintage sled that’s truly one-of-a-kind, few pieces tell a story quite like the Vermont-made jack jumper. Unlike traditional sleds or toboggans, jack jumpers were designed for downhill fun on steep, snowy slopes using nothing more than a sturdy wooden ski with a simple seat attached. Popular with kids (and daring adults!) throughout rural Vermont in the early 1900s, they’re now rare finds that collectors and vintage lovers alike treasure.

Over the years, I’ve picked up three jack jumpers here in Vermont, each one with its own character and rustic charm. These nostalgic sleds instantly elevate a winter porch display, adding that authentic New England feel that’s so hard to replicate.

Come winter, I dressed up a bright red jack jumper with fresh evergreens and a burgundy bow, placing it right on the snowy steps. It’s such a simple yet striking way to use these sleds in holiday decorating, and a fun alternative if you’re looking for something different than the classic toboggan or flyer sled.

Whether you lean them against a wall, pair them with greenery, or use them as quirky accents in a larger winter display, jack jumpers are a charming way to decorate with a vintage sled while celebrating a unique slice of New England history.

Adding a vintage wooden sled or toboggan to your winter decor is a wonderful way to bring rustic charm and nostalgia into your home. Whether displayed as a Christmas present accent under the tree or styled on your porch with greenery and lights, these timeless pieces add a little vintage touch that’s both cozy and unique.

Embrace the magic of the winter season by repurposing these classic sleds into charming focal points for holiday inspiration.

Decorating with vintage pieces adds so much character and charm to a home, but few things capture winter nostalgia quite like an old sled. Whether it’s a classic toboggan, a Vermont jack jumper, or a flea-market find, there are countless ways to decorate a vintage sled and let it shine as part of your seasonal styling. From porches dusted in fresh snow to cozy entryways, these timeless treasures tell a story while adding warmth and whimsy to your winter decor.

Looking for even more inspiration? Explore my full Vintage Ski Lodge Decor: A New England Guide to Holiday and Winter Styling, where I share snowshoes, skis, and other alpine antiques styled for the season.

Frequently Asked Questions About How to Decorate a Vintage Sled

1. How do you decorate a vintage sled for winter?
The easiest way to decorate a vintage sled is to lean it against a porch, entryway, or wall and dress it up with seasonal accents. Add a plaid scarf, a bundle of fresh evergreens, or a pair of mittens tied with wire for a charming, rustic look. A simple bow or strand of twinkle lights instantly makes it holiday-ready.

2. Can I use a vintage sled indoors for decoration?
Absolutely! Smaller sleds or toboggans can be styled inside by hanging them on a wall, placing them in an entryway, or pairing them with winter accessories like ice skates and scarves. Indoors, they add cozy ski lodge charm without being exposed to the elements.

3. What’s the best way to keep a decorated sled from falling over outside?
If you plan to display your sled outdoors, make sure it’s secure. You can prop it against a wall and use gardening wire or zip ties to fasten it to a porch beam, railing, or garland. This keeps the sled stable even in snowy or windy weather.

4. Where can I find vintage sleds to decorate?
You’ll often find vintage sleds at antique shops, flea markets, and winter markets. In New England, they’re a staple at places like Vintage Market Days Vermont. If you can’t find one locally, check online shops like Etsy or eBay for a variety of sled styles, from toboggans to classic flyers.

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