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Winter Engagement Ideas

Are you looking for cute winter proposal ideas?

Yes, to proposal season. 

Most wedding proposals happen between November and February. 

And in honour of that, we came up with various romantic winter proposal ideas you can choose from for your proposal. 

Now that you have purchased that gorgeous engagement ring, it’s time to think about how you will propose and where. 

Asking anyone to marry them can be highly stressful.

Planning a proposal is a highly emotional event and is a big deal. 

You are committing to spending the rest of your life with that special person. 

If you have picked the perfect diamond engagement ring or the ring of your choice and are not looking for the perfect proposal ideas, then we have you covered. 

Lucky for you, we have a few awesome ideas you can use to ensure your proposal is one that your partner will never forget.

I love the winter season, and since the Holidays are just around the corner, I figured a romantic winter proposal is just what we needed.

I am not sure where you are located, but here in Canada, the winter season typically starts around late November until about March.

And believe it or not, winter is a popular month for couples to get engaged. 

That is because it is the most romantic time of the year. 

I believe this. 

Think of all the holiday lights, Christmas trees, snow and everything else that comes with winter. 

Most cities are usually transformed, and the results are simply magical. 

From surprise Christmas tree decorations to a romantic winter getaway for two, you will find a great list of winter proposal ideas you can use this holiday season.

Here are a few things I will be covering:

  • Romantic winter marriage proposal ideas

  • Different types of surprise proposal ideas

  • Best tips for how to propose in the winter

  • Tips for planning a winter wonderland proposal 

Getting down on one knee to propose is a big deal that does need some planning if you want it to be remarkable. 

We know expressing love and emotions for your partner is not always easy.

If you plan to pop the much-awaited question and want to do it over Christmas or the holiday season, buckle up, as we have a lot of fantastic winter holiday proposal ideas. 

So how do you propose in winter?

Before we get started on our most romantic winter proposal ideas, we wanted you to take the time to like our Facebook Page here! We also use affiliate links in our blog posts, meaning we can make a commission if you use any of our affiliate links.

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19 Romantic winter marriage proposals to get you inspired:

The winter months are the most romantic time to propose to the love of your life. 

Something about the holidays, fresh snow and hot cocoa makes Christmas time exciting and romantic. 

And since Christmas is just around the corner, we wanted to share a few fantastic winter proposal ideas you can personally use. 

Choose a proposal idea that works for you both. 

Avoid sticky situations that can embarrass you both. 

The goal is to be romantic and to get a “hell yes!”

With that in mind, here is a list of romantic winter engagement ideas worth checking out:

Romantic winter wedding proposal ideas! Are planning to propose in winter? These winter proposal ideas are perfect for you. Winter and the holidays are perfect time to propose.

1. Super romantic winter proposal by the fire

Nothing is more romantic than a cozy fireplace during winter to stay warm.

If you have a fireplace at home, I suggest you use it to your advantage. 

Decorate the mantle and make sure it is just perfect. 

Cook up a delicious warm meal for two, and cozy up by the fireplace to enjoy your meal. 

You can reminisce about your love life and tell her why you think she’s special. 

Keep it light and fun while you work up to the big question. 

After you are done with the meal, grab some winter dessert treats and pop that question. 

If you want to be fancier, take her to a restaurant with a fireplace and surprise him or her with a romantic proposal after dinner. 

2. Book a romantic winter carriage ride

Winter is popular with horse-drawn carriage rides around the city.

If your city or area has these services, make arrangements ahead of time. 

Make sure to go in the evening, dress warmly and cozy up with some hot chocolate or any warm beverage. 

Just be sure to have a place to set it down so you can adequately propose to the love of your life.

Hopefully, the weather corporates and you have light snowfall, making for a very romantic setting. 

If you can hire a photographer to capture the moment, even better. 

The best winter proposal idea is one that is captured either on camera or in film. 

3. The first drop of snow winter proposal

This one is one of the most romantic ways to propose in winter. 

Everyone loves the first drop of snow. 

This is usually a sign that winter is just around the corner, and the grounds will soon be covered in snow. 

I loved seeing the first snowdrop as a kid and still enjoyed it as an adult. 

If you are feeling romantic, plan to propose to your significant other at the first sign of snow. 

It will take some creative planning from you. 

Ideally, the best timing is when you wake up to that first snow on the ground, wake your partner up and go outside to enjoy it.

From here, you can lead up with your romantic proposal, followed by coffee and breakfast in bed. 

And if it happens to be in the evening, make a romantic dinner with a nice glass of wine or champagne to celebrate. 

Organize the best winter WEDDING PROPOSAL! Surprise Wedding Proposal is one of my favourite type of photoshooting. A surprise proposal is romantic and even more romantic during winter. Check out these cute winter proposal ideas.

Source: Laura Harrish Photography

4. Write it in the snow

If you want a simple winter engagement proposal idea, this one is. 

Except for the engagement ring, you don’t need to spend much money on this romantic winter proposal idea. 

You can write your proposal in the snow itself if there is enough fresh snow. 

Nothing is more romantic than seeing that “Will You Marry Me?” question on the ground as you ask your partner to run errands, go for dinner or meet the family. 

I am sure they will love it, especially if they love snow. 

To make this winter proposal idea even better, use rose petals and candles or have your friends and family lay in the snow to spell it out. 

How fun would that be?

5. A coffee shop proposal 

We are sharing so many great winter marriage proposal ideas we knew we had a few coffee lovers that enjoyed reading the blog. 

So naturally, we needed to include a coffee shop winter proposal idea. 

Do you or your partner love coffee?

I am a huge coffee lover.

My day doesn’t officially begin until I have had a nice cup of coffee.

If this is you, then this coffee shop-run proposal is perfect for you.

If you have a go-to coffee spot in town and make the arrangement.

Maybe ask the management team or the barista at your coffee shop to write a short romantic proposal quote or message on a cup or even a napkin.

You can even use these simple “Happy I found you” quotes to have them written on the coffee or the coffee cup. 

Be sure to involve the coffee store management and team to help you write something in the coffee cup or sit somewhere private at the coffee shop and propose. 

Either way, this winter proposal idea is romantic if your partner loves coffee. 

Cute Coffee Shop Engagement Idea! Coffee shop engagement photo session. |Engagement photo inspiration | Candid photography | Intimate moments | Engaged | Coffee shop photo shoot | In love | Sweet moments | Couple goals | Organic photos | Lucky in love

Source: Dan Cox Photo

6. Plan a surprise winter proposal party

If your SO (significant other) likes surprises, invite all your friends and family to celebrate your engagement.

A surprise proposal is romantic and even more romantic during winter.

An intimate party would be ideal for this exceptional occasion. 

With a smaller guest list of just your closest friends and family, you can host an intimate party at home or in a small venue.

This is perfect as it is the holidays and most people would want to spend this time with their own family. 

So it doesn’t have to be a huge gathering. 

Throwing the perfect winter proposal party takes a bit of planning.

Keeping to the tradition of a surprise proposal, ensure your partner doesn’t find out about the engagement party. 

Send out invitations, choose a venue or location, and budget for the party, 

Ensure everything is kept under wraps. 

One of your loved ones could record your proposal from a distance or take pictures.

Your winter wedding proposal should include the following:

7. A cozy walk winter proposal

Walking or thinking is one of the best winter proposal ideas if you know your significant other loves this activity. 

I know some pretty avid hikers. 

Don’t let the cold weather stop you from taking a walk. 

Going for a nice walk during winter in the early morning or late afternoon is perfect for proposing. 

While on your lovely walk, declare your love and feelings to your SO. 

Pull out the engagement rings and summon those unique words you prepared regarding what you will say when you propose.

This could be the most romantic winter wedding proposal if you are both avid hikers and do not mind the cold.

Choose a nice place to hike that is safe during winter, dress warmly and find a special spot to propose. 

And don’t forget to have some fun in the snow. 

29 Unique winter Proposal Ideas For Unforgettable Pop The Question! Check out these Dreamy Winter Proposals That Will Have You Swooning This Season! It’s our favorite time of the year! As the holidays roll around, so do grand gestures.

Source + tips: Andrea Stark Photo

8. A romantic sleigh ride proposal

There are so many fantastic winter proposal ideas.

You need to pick one that resonates for you most as a couple.

And a sleigh ride proposal is one I feel anyone would love. 

If you often look at that engagement ring you recently purchased for your SO and are thinking about how to propose during winter, you should consider a sleigh ride winter proposal. 

This is the ultimate Cinderella prince proposal idea that women like. 

A sleigh ride is a romantic way to propose to your partner during winter. 

Who doesn’t love sleigh rides? 

Enjoy the relaxing ride around town with a cozy blanket. 

Tell your partner exactly how you love them and how you want to spend the rest of your life with them. 

Once you stop, help her down and get down on one knee (you are already holding her hands) and propose. 

There is nothing more romantic than that. 

You can go on a horse-drawn sleigh through the park or a dog sled through the woods.

You have options. 

9. Fun romantic winter activity proposal idea

For great outdoor winter proposal ideas, read this section.

Don’t stay scooped up inside the house in winter.

Get outdoors and enjoy yourself.

As long as you are dressed for the occasion, you can enjoy some awesome outdoor winter activities.

I will not lie; I wouldn’t say I like winter, and spending time when it’s cold outside is not exactly my cup of tea. 

But I also do not mind enjoying some fun winter activities once in a while. 

You have won half the battle if you both enjoy the great outdoors during winter. 

You are halfway into planning the perfect winter proposal. 

Here are a few romantic winter activities you can plan for an excellent opportunity to propose o your partner: 

  • Spa date
  • Snowboarding 
  • Skiing 
  • Hiking

Plan a luxurious spa proposal if your partner enjoys papering herself.

Or go to a ski resort and propose at the bottom of the hill.

Follow this up with a romantic candlelit dinner to warm up. 

Whatever you choose, these winter proposal ideas will always be remembered.

10. Skate your way into a proposal

Do you enjoy skating in winter?

Ice skating is a great winter activity enjoyed by most couples. 

If you traditionally skate, then your partner won’t suspect a thing. 

This makes it the perfect setting for a romantic winter proposal.

Whether you enjoy skating outdoors or in an indoor skating rink, this one makes for a romantic proposal in winter.

You can propose in front of everyone or see if you can rent out the rink for privacy. 

I love the idea of having the rink to yourself, setting up the rink with flowers, and proposing to your partner. 

This can also get expensive, so if you can’t do it, that is okay too. 

Find a small corner, and get down on your knees to propose. 

This winter wedding proposal is only romantic if you both know how to skate. 

A cute winter wonderland proposal. Check out these romantic winter proposal ideas worth stealing if you plan to propose this year.

Source: The Bartnett Company

11. Cute surprise winter photo shoot proposal

This is a brilliant idea as you would have captured the special moment. 

Tell your partner you have planned a Holiday couples photoshoot to make Christmas postcards. 

This will allow them to dress up and look their best. 

You can even have a theme, like a picnic photoshoot and bring all your props. 

Most photographers encourage props. 

Let your photographer know that you plan to propose and let her queue you. 

During the photoshoot, you can bend down on one knee or hold up a sign or proposal with whatever vision you have.

You will have photos of that particular moment to share with others at your wedding. 

12. A family affair winter holiday propose

Are you looking for cute surprise proposal ideas with family?

Holidays are meant for spending time with those you love.

Visiting your loved ones over Thanksgiving, Christmas or New Year’s means a lot as you create fond memories.

Most of us are busy during the year with work commitments, kids and other summer bucket lists and activities to get through. 

It’s natural to start unwinding during the winter holidays in time for the near year. 

That’s why winter proposals are excellent. 

End your year on a high note and start a new year with a fresh leaf (or ring). 

Make this winter gathering special by combining families, going on vacation or at someone’s house for this surprise Christmas proposal. 

Family is important, and having them involved with the proposal makes it unique and one to remember. 

29 Unique winter Proposal Ideas For Unforgettable Pop The Question! Check out these Dreamy Winter Proposals That Will Have You Swooning This Season! It’s our favorite time of the year! As the holidays roll around, so do grand gestures.

Source: Catherine Milliron Photography

13. Propose next to a Christmas tree

I love Christmas marriage proposals.

This idea is cute for those looking for fantastic wedding proposal ideas for Christmas

Christmas is my favourite time, and I am already counting the days until December. 

If you or your partner love Christmas, these Christmas marriage proposal ideas will work for you. 

There’s nothing quite like a surprise proposal on Christmas or around the holiday season. 

There are so many ways to propose next to a Christmas tree. 

Here are a few of my top Christmas marriage proposal ideas by a tree:

  • Go shopping for a tree at a Christmas tree farm. Once you decide on a tree, get down on one knee and propose. You can also pre-plan this by picking a tree and setting up a blanket in front of it with Champaign and some glasses. 
  • If your town or city hosts Christmas festivals, I am sure an extravagant tree is fully decorated. Propose in front of this. Don’t forget to include your family and friends by attending the festival as a group. 
  • Decorate your tree at home, have the ring tied with a cute ribbon and hang it on a tree with the other ornament. When she notices it, give her your well-prepared proposal speech. 
  • Use a ring box tree ornament to propose to your partner by handing her the ornament while decorating the Christmas tree. 
  • Propose on Christmas day while you open gifts around the Christmas tree. 

These are all romantic winter proposal ideas that can be done in front of a Christmas tree. 

14. Christmas morning wedding proposal

Here are a few more wedding proposal ideas at home that are perfect for homebodies.

Proposing on Christmas day has got to be the most romantic thing ever. 

After all, Christmas is the most popular time for proposals.

Try this laid-back idea if you are looking for fabulous wedding proposal ideas for Christmas. 

If the timing is magical, then take the giant leap and propose. 

The perfect time to propose is during the gift-giving or exchanging gifts if it’s just the two of you. 

The proposal involves presenting the engagement ring to your partner as a Christmas present.

You can propose in front of your family or in private. 

If you don’t have kids yet, I would prefer a quiet romantic Christmas morning proposal for just the two of you.

15. Will you marry me? mug

This is one of the best winter proposal ideas for coffee lovers.

Refer to option 6, where I encourage you to propose in a romantic coffee shop. 

Can you tell that I love coffee? 

If you don’t like proposing in a busy coffee shop, this section is for you. 

Winter and chilly weather are cuddle season. 

It’s an opportunity to get out your favourite cozy blankets and cuddle in front of the fireplace or front of the TV. 

There’s nothing more romantic than cozying up with your partner when it’s cold outside.

After dinner, cozy up and serve some warm drinks (think hot cocoa /coffee) and pop your question while serving her portion in a customized “will you marry me?” coffee mug!  

Bonus, she will have the mug to drink out of forever (as long as it doesn’t break)!

Will you marry me mug for those planning to propose to a coffee lover. If you are looking for cute engagement proposal ideas, this is a cute idea.

Grab this mug here!

16. Cute surprise winter photo shoot proposal

This is a brilliant idea as you would have captured the special moment. 

Tell your partner you have planned a Holiday couples photoshoot to make Christmas postcards. 

This will allow them to dress up and look their best. 

You can even have a theme, like a picnic photo shoot, and bring all your props. 

Most photographers encourage props. 

Let your photographer know that you plan to propose and let her queue you. 

During the photoshoot, you can bend down on one knee or hold up a sign or proposal with whatever vision you have.

You will have photos of that particular moment to share with others at your wedding. 

17. Plan a romantic winter getaway proposal 

This section is for you if you are searching for vacation proposal ideas.

Holidays are for travelling somewhere romantic.

Just look up NYC winter proposal ideas or places to propose in Connecticut. 

You will be met with so many winter wedding proposal ideas worth stealing. 

The best place to propose in winter that is romantic:

  • Chicago
  • Ottawa
  • Paris
  • Lisbon
  • Quebec City
  • New York City
  • Montana 
  • Colorado

Cold winters mean fewer crowds. 

Unless you travel somewhere nice like these vacation spots for couples during winter, you won’t typically find crowded places with tourists. 

Most people enjoy travelling to beachy areas during winter. 

I suggest planning a winter getaway if you are planning for a romantic winter proposal.

Many destinations can offer you stunning backdrops for a perfect winter proposal.

I would love a romantic getaway in winter, especially if a proposal were planned.

Planning a winter vacation proposal? Check out this romantic Surprise winter Proposal! Find the The best place to propose in winter that is romantic.

Source: Carley Teressa Photography

18. A New Year’s Eve proposal over fireworks

Winter is just not Christmas or December.

You have between November and February to use these romantic winter proposal ideas. 

If you are not going with the classic Christmas proposal, your next bet is a beautiful New Year’s even marriage proposal.

With fireworks, champagne, fabulous outfits and surrounded by family and friends, this could be the best new year’s eve winter wedding proposal!

What more could you ask for?

If you plan on attending a planned New Year’s Eve party in the city, most of the hard work will be done. 

If it’s an outdoor New Year’s eve party, find a romantic place for the countdown to propose as soon as the countdown is done and the fireworks start.

A simple “will you marry me would be enough as they would be too much noise.

Then hit a restaurant or a bar to enjoy some champagne & celebrate. 

If this is a private party at a family place or with friends, inform them of your intent to propose.

Be open about your surprise proposal plan, as most people would rather watch the fireworks. 

When the countdown starts and reaches down to four, three, two, one – turn toward your partner, get down on one knee and pop your question. 

This will be an unforgettable winter proposal for both of you.

19. A Valentine’s Day proposal 

If you plan to pop the question on the 14th, I am all for it.

Valentine’s Day proposals are just romantic and charming. 

February 14th is a day dedicated to celebrating love, so why not propose on this special day? 

Here are a few super cute Valentine’s Day proposal ideas: 

  • Pop the question with a ‘marry me’ candy or sweet pink desserts
  • Plan a weekend getaway to propose
  • Breakfast in bed Valentine’s day proposal
  • Leave a trail of red petals/ candlelight leading up to you holding a ring
  • Recreate your first date 

There you have it, the top best proposal ideas for the winter!

Romantic winter wedding proposal ideas! Are planning to propose in winter? These winter proposal ideas are perfect for you. Winter and the holidays are perfect time to propose.

What did you think of all our winter wedding proposal ideas?

Which engagement proposal stood out the most?

Let us know if you have a fun winter proposal story about how he asked you to marry him.

We want the whole story.

We would love to share it. 

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19 Romantic Winter Proposal Ideas For Winter Lovers