Chic Tented Wedding at Home with Hamptons Wedding Planner Ashley Douglass

We specialize in tented weddings and at private homes and estates. Tented weddings at home are some of our absolute favorite weddings. Our clients that host their wedding at home allow us to make the best use of our two decades of experience, and they are so fun to plan on the design front and clients! There is nothing that comes close to a tented wedding at home.

They are not as hard as you think if you hire a planner such as ourselves. We know this project inside and out, and they energize us too. We will let you know what to expect and how we are going to handle pre-production, execution and strike, so nothing is a surprise.

Contrary to popular belief—or fear—a tented wedding in the rain is fantastic. There's nothing quite like a hopping party under a tent in a storm. Yes, it's safe, and we always know how to prepare for it. This wedding was on September 6th, 2025. If you remember that day and were in New York State, you know how terrible the weather was! But this wedding was phenomenal.

For the ceremony at the Shelter Island Beach Club, the weather was touch and go. As a planner, I keep in touch with other weddings nearby when we're at a tented site in an area with many weddings, such as the Hamptons. We knew it was already raining in Watermill and really coming down in Quogue. The sky was getting darker above us, so at the last moment we decided to move the chairs and ceremony into the rain tent. The bride and groom like funky things, so they beautifully shifted like champs and got married in front of the lifeguard stand that was intentionally positioned on the perimeter of the Sperry tent. In cases like this, when bad weather is predicted, most couples opt for the rain plan. This couple decided to risk it, though we still had to put the rain plan tent up, of course, to be safe. Luckily, this is one of those venues where we could put a rain tent up in a nearby location that wouldn't prevent us from having the wedding in the ideal weather location.

Planning this tented wedding weekend on Shelter Island and in the Hamptons was such a gift. The couple listened to our recommendations—don't only look at photos of weddings for inspiration. In fact, start your wedding design ideas with things, anything really, that aren't pictures of other couples' weddings. Look at interior design, scenery, music, perhaps photos of places you've traveled together and have fond memories of, or artwork, restaurant design, hotel design, and more. We want to find a small spark (or large one) that gets at something that makes you excited and can lead us in a direction that's bound to be something we haven't designed before.

We love planning weddings on Shelter Island. Shelter Island has a feel like none other - the most relaxed luxury one can find in New England. Plus, your guests have the option to stay in either the North Fork like Greenport, NY or in the Hamptons be it Sag Harbor or East Hampton or Bridehampton, ideally. When we work on Shelter Island we have contacts that can arrange for a later ferry shuttle back to the main land beyond the times that are often offered with the regular Shelter Island Ferries.

The first note Bride, Claire gave on design was for the wedding to have some plants. That is it! We want tons of plants and noting that is deliberately wedding. Nothing that would cause us to ”cringe” in the least bit. I brought up the idea, ‘what if we poked fun at weddings’ and that was a hard “YES”! I came up with the idea to have a cake design that is currently trending but to intentionally have the cake maker build it as though it is falling down. It was a home run! Originally they didn’t even want wedding cake. The last thing you want is a wedding menu that screams banquet halls of weddings past. We design a menu that was deliberately strange. Is it a shark, a paddle board, doesn’t matter - it’s cool.

I hope you enjoy this Tented Wedding at a private home it the Hamptons on Shelter Island as much as we do!

(3/10) Top 10 things to remember when planning a wedding...the less superficial list.

Three of Ten: Wedding planning can be simple if you know what the skilled planner knows.
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As always, what we write below does not apply to everyone.
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Right now, you may not believe that wedding planning can be simple but it’s true. So is the fact that what’s simple is hard. Wedding planning and any project, no matter its size, is simple if you have the time, experience, support and know what's ahead of you. It’s sometimes hard to accept what you learn as you move along because your assumptions will be tested. If it’s not time, experience, or a fear of the unknown getting in your way, then it’s your feelings about what’s happening, or things entirely separate from the project of wedding planning. If you don’t have the willingness to address all your feelings during this noteworthy time, then you are prone to project your feelings onto other things, such as your wedding planning.
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For some of you more than others, the time of your engagement and wedding planning brings up a ton of feelings. In other words, questions, expectations, fears, baggage from your childhood and your present-day insecurities. All normal stuff that is not all about shooting stars and fairy princesses. All normal stuff. You are not odd or alone in this.
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Take planning one step at a time and don’t fling your attention all over the place. Above all, hire help or enlist a levelheaded friend you trust. If you do hire help and your help has done this over 200 times to great success, trust them.
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Simplify your life a little so you can give yourselves time for all the things that come up this year, so that the actual wedding planning is simpler. If you take time for all your feelings, at the end of the road I promise that you will feel more ready, happy, and carefree on your wedding day.
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Don’t fall down the rabbit hole and have a year that is constantly in manic-mode and reassure yourselves by saying, it’ll all go back to normal once the wedding is over because it won’t, not entirely anyhow. If this describes you month after month after month after month, some other things are going on and after the wedding, when you crash, you will be left with the realities that you avoided beforehand.
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The process will be much simpler for you both if you get specific about the intention of your wedding. Yeah, yes, we know you want to celebrate with your friends and family, and for everyone to have a blast. But truly what is your wedding for and what is it not for? Aim your energy at the positive answer and try and let all the other bullshit fall away. Respect your own wedding - stick to your intentions. You are choosing to not just go to city hall for a reason, right? Well, why?

MEGAN + TIM | Montauk Lake Club | Montauk, New York

Megan and Tim came to us pretty far in advance. In fact, they were the first to book for 2017 about 23.5 months out from their date and wisely so because they wanted to get married in Montauk. When they first booked they didn’t have a venue which is perhaps the hardest choice you will make. They are as familiar with the area as we are so in that regard making this choice wasn’t hard but pulling the trigger (or price tag) was. The variance of price amongst some venues out East is great. Learning where your priorities lay can take some time or change once you really delve into planning. In the end they chose the Montauk Lake Club because it was quiet, private, available over more preferred dates, and one of the more favorable options financially. It’s also a tented site so you can certainly do whatever you want inside the tent! The staff is very nice as well. ;-)

Megan and Tim both work a ton. I know everyone can say that these days but let me explain…..Ashley would have calls with Megan while she was in the middle of overnights. In other words, a night where she would sleep on her desk, in her office, at the law firm. YUP! Tim simultaneously worked full time while earning his MBA at Columbia University. Got enough on your plate? To add to the pot, the summer before their own wedding and the summer of their wedding, they attended more weddings than ADE planned. Now think about that…Working all the time and between the 18 or so weeks from Memorial Day to just past Labor Day, they attended more weddings than there are almost weekends. On top are the engagement parties for the year after, bachelor and bachlorette parties, not to mention their own parties! They are one of our couples that we refer to as ‘professional wedding attendees’!

Laid back and fun was most important for this weekend. Nothing stuffy, nothing formal and nothing that is truly not needed. Invites that made them excited, linens that popped with indigo, with lots of greenery and a great band! They booked their band just a week out from booking us! As I always do, I talked about music when I first met them. Very fast I knew they’d love this band and low and behold they were the same band a friend of theirs used that they loved and had forgotten the name of. Good thing we moved fast because often enough the Marcus Reid Band books upwards of two years out or more. They were a wild crowd that danced more than most, ties on heads, people on friends shoulders, you get the picture! This wedding was one of the most fun - hands down!

Photography below by Craig Warga Weddings 

Planning + Design | Ashley Douglass Events

Florals + Design | Blade NYC

Photography | Craig Warga Weddings

Venue | Montauk Lake Club

Gown | Vera Wang

Band | Marcus Reid Band from Hank Lane

Cinematographer | Orange Films

Hair & Make up | Blushington

Tent | Sperry Tents Hamptons

Invitations | Katie Fischer Design

Cake | Momofuku Milk Bar

Rentals | La Tavola Linen

Rentals | Party Rental LTD