3 Tips for Winter Outdoor Entertaining

This post “3 Tips for Winter Outdoor Entertainingis sponsored by Troy-Bilt. Thank you for supporting the brands that support for our blog. We hope you’re inspired.

It’s winter here in the Hudson Valley, New York, but that won’t stop us from using our outdoor space. This past fall we started working with Troy-Bilt to create a patio in the woods for entertaining this winter and into the spring and summer. After a long stay at home order in New York last March, we realized how much more we valued our outdoor space. Over the summer we would invite a few friends over to hang out around the grill and fire pit, socially distanced. After not socializing for months, that little bit of outdoor time we spent entertaining was extremely valuable and luxurious to us. We’ve adjusted how we socialize to respect social distancing – and it’s possible to have a really lovely time. 

In the early winter we started working on an outdoor patio area. We’ve never worked outside in the winter but needed to in order to clear the area while we could see through the forrest, it’s too overgrown in the warmer months to even know where to start. We felt like we made really great progress and enjoyed having a project outside. The winters can be long here! In the future we’ll have a winter outdoor project like clearing, wood cutting or chipping because it was so nice to work out side and helped shorten the winter and keep our minds and bodies active. As soon as the snow clears we’re going to get back out there and keep working.

We shoveled a path to the backyard gate where a table awaits with a drink.

A History of Entertaining

Our house is a hub for large scale entertaining. And not just us as owners, but back to the 1800s when Charles Backman, the horse breeder, would have gentlemen of note over to buy horses and smoke cigars. Or Les and Fred, the owners previous to us, would have big parties here to escape life in the city. The soul of this house is to be shared with people. It has been sad to see it empty for the past year. I love a good problem to solve (after all, we did buy an old house with tons of problems!). Entertaining during a pandemic and when the weather is cold a challenge, however I approached it with the same problem solving skills I would any other project. 

Tips for Entertaining

I thought about the challenges of the pandemic and weather. Here’s our tips for brightening someone’s day and sharing your outdoor space in colder weather. 

One: Ask and Listen

One of my biggest challenges with entertaining is everyone is quarantining a different way. We have some friends who are not seeing anyone, others who are in a pod and then others who are out and about regularly. We just never know! When I host a dinner party, I always ask things like do you have any dietary restrictions, or I ask what people would like to drink making sure I have something non-alcoholic available if they happen not to drink. If I’m being a good host, I send an email and simply ask. Here’s what my email says regarding getting together during the pandemic. 


Hello Friends! 

It’s been a long winter indoors and we were wondering if you’d allow us to entertain you? Yes, we know it’s a pandemic and everyone has different comfort levels. Tell us what you’re comfortable with and we’ll create an experience to get you out of the house for a little adventure. 

  1. I’m not seeing other humans right now. Totally fine! We’d still like to invite you over. We’ll wave to you from the back porch.
  1. I’m okay seeing you but outdoors and with a mask. We’re good with that too. We’ll keep our distance, wear a mask and say hello. 
  1. I don’t even care, just get me out of my house. We’re cool with seeing people outdoors, at a distance. Please come over and we’ll chat for a bit around the fire pit.
  1. I want to see you and give you a hug. We love you too, but no hugging. Nope. 

Let us know what you’re comfortable with. We know everyone has a different situation. Some of you are in pods, some of you are working in a higher exposure job – whatever works for YOU! Here’s where we’re at: We’re comfortable seeing people outside, at a distance. It’s really hard to remember to keep a distance, but hopefully with the way we have the space set up, it will be easy to remember. If you’d rather not see humans but want to get out of your house in a safe space, we got you. Allow us to treat you.

Email back and let us know if you want to come over and when. Dress warm! 

XO Susan and Will


A communication like this opens up a conversation. When our friends reply, I listen and do my best to make their experience wonderful. After I got thinking about the idea of entertaining, it became about sharing our outdoor space as much as seeing our friends. And another big component of making a nice experience for friends, is the mental health aspect. This pandemic has been one of the most difficult mental health moments in my life – and I think a struggle for a lot of people. The absence of seeing others. If we can offer someone a bit of hope – we’re showing up for it. 

Once you arrive at the back yard gate, grab your drinks and go.
We have a drink for each person and a note (we are not seeing them) telling about the next destination.
Then they turn and look through the gate and see the path.

Two: Zones and Paths

I love a good event experience. Living in NYC, we’d go to some wonderful events that got your emotions going. Or a great wedding – remember those types of gatherings? We have a larger property that we’ve used to create different zones. At each zone there is something to discover. For friends that we aren’t seeing, we’ve left a little note so they know what to do next. 

We created three zones. A drink zone, a food moment and a DIY dessert. Three stops on the journey. If we are seeing friends, we meet them at the fire pit. It’s easy for us to stand across the fire pit to keep our distance. A natural 6 foot reminder to keep some space. 

The fire pit area was previously filled with the dreaded multiflora rose, thorns galore. Before the snow fell we had cleared the area with the trimmer mower and removed the stumps, you can read about that here. The trimmer mower helped us keep our distance from the thorns, which was amazing, and made the job go so much faster and cleaner. It is so about the using the right tool for the job!

To join the zones together we made paths and in one area lined the path with lanterns. This is one of the easiest and most elegant ways to enchant a guest. A guest knows where to walk even if we can’t be there to guide them. 

Once they walk down the lantern path, the garden gate is open.
They can sit and have a little bite.
I put the soup out in a closed container and our guests can serve themself.
The soup is homemade by Will and uses a pumpkin, onion and garlic we grew in the garden this past summer.

Three: Drinks and Design 

Drinks and Food: The cold weather gives us the perfect opportunity to serve hot cocoa, home made soup (made with a pumpkin grown in the garden) and s’mores over the fire pit. I love the individual containers for serving during a pandemic – I can make the drinks in advance and set them outside. For food servings, I like to present in containers per household. If we were eating without guests, I would make a separate serving container for us. Trays help keep me organized like that. 

Design and Styling: Whether we’re in a pandemic or not, entertaining has to be easy and no fuss or it becomes ‘work’. I have a set of items I can pull together that make it look like I spent hours setting up a space. I use one trick to pull everything together and that’s color. Pick a color to focus on as you grow your collection of outdoor entertaining items. My color is blue – this almost feels like a Steel Magnolia moment. I could profess for hours about my ‘signature color’. I can walk around my kitchen grab a few items with blue, head over to the linen closet, grab a few blankets with blue and all of a sudden it looks like a party. 

In the cold weather this set up works wonderfully! If it’s on the colder side, it would take about 30 minutes to walk through the space and enjoy the treats at each zone. While that doesn’t seem like a lot of time, the excitement of getting out of your house for a little bit and being somewhere new is a treat in itself. If it’s warmer outside and the fire pit is kicking off some heat, we spent 2 hours outside the other day! It was really nice and felt normal. 

When we stared the outdoor patio project in the middle of winter, it was such an eyeopener about the importance of spending time outside in our own yard, year round. Even if it was only a few hours a day, it was such a nice break to be outside. Every year we do one or two big things in our yard to make it just that much more enjoyable, and having a plan and the right tools goes a long way.

We hope you’re inspired to entertain in a new way this winter and these tips take you into the warmer weather. 

The next destination is the fire pit. We have another drink (if our guest needs a refill) and all the supplies for s’mores. Our guests will have to toast their marshmallows to their liking and enjoy a sweet bite.
We also leave another note thanking them for tier visit.

This winter outdoor entertaining post is sponsored by Troy-Bilt. Thank you for supporting the brands that support for our blog. We hope you’re inspired.

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