Chic Tented Wedding at Home with Hamptons Wedding Planner Ashley Douglass

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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!

Fall Cedar Lakes Estate Wedding Planner, Hudson Valley, New York

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It's not every day that wedding planners with high standards for hospitality find a weekend-long wedding venue that not only meets those standards but works alongside our team as though we've been collaborating for years. Cedar Lakes Estate, the Hudson Valley-Catskill wedding venue, checks this box 100%. It's a breath of fresh air.

As much as design may be your passion at the start of planning, it won't matter more than how your wedding unfolds overall. Were you taken care of? Were your guests taken care of? Did your planner lead you in the right direction? Did each vendor perform to the best of their abilities? Did your planner help you make the most of your budget and anticipate your needs during planning and throughout your celebration weekend? Was your entire planning team—and every vendor you hired, including the venue's staff—happy and energized while working tirelessly on your wedding day?

If your event isn't planned with you both in mind and executed seamlessly, the aesthetics won't rise to the occasion. People traveling to celebrate you truly care about being taken care of. You want your venue to feel like your closest loved ones are coming to Thanksgiving dinner at your own home—acknowledged, appreciated, and cared for. When you meet these standards you two will have the most fun you could possibly have. And then, your wedding design will have you feeling satisfied, happy, and excited! 

Cedar Lakes Estate opened their new glass house this past fall of 2025. We were lucky enough to use this stunning new space for Emily and Ben's rehearsal dinner before their welcome party. The space was actually 90% complete, but they graciously allowed us to use it anyway. We went to great lengths to conceal the unfinished parts, and no guest would have known otherwise. This is a testament to treating your vendors well—they didn't have to allow us to use this space, but they did! It allowed us to keep the more intimate rehearsal dinner entirely separate from the welcome party that took place afterward. The glass house is also the perfect space for a ceremony rain plan, as it still brings the outside in!

We don’t have all the photos just yet and can’t wait to spill over them and share them with you all soon enough!  This couple has such a beautiful and funny at times, love story. We cannot wait to tell it with all the photos forthcoming before 2026. For one, you can find their very own lover’s bench in Central Park! Yes, a permanent bench. They are a true New York Story and we were so grateful to be a part of it. Such fun-loving and warm families!

This is your sneak peak with our great friend and photographer, Sasithon from Wedding Artists Collective.

Some loving words from these clients that we absolute love!

“The Absolute Best: A Truly Magical Wedding Weekend! We cannot recommend working with Ashley Douglass more highly—she is the absolute best. Working with her was a truly exceptional experience that resulted in a spectacular, magical wedding weekend. Ashley is a master of creativity, style, and taste, and she seamlessly brought this wedding vision and dreams to life. Every single part of the weekend felt infused with love, care, and originality. What truly sets Ashley apart is her professionalism and demeanor: she is a drama-free event planner who handles complex logistics with grace, and her team is just as wonderful! She and her team consistently treated everyone—from our family to all the vendors—with great respect, representing our needs and style perfectly. Her vendor curation is outstanding. She introduced us to the very best and most creative professionals, who were all excellent and lovely to work with. We loved truly all of our vendors - photographer, videographer, band, venue, floral design...all were spectacular. Furthermore, Ashley's attention to detail extended to our family, as she proactively took all the needs of our older relatives into account, ensuring comfort and joy for everyone. Choosing Ashley was, without a doubt, the best decision we made. We are still riding on the joy of the beautiful celebration she created.”

Revisting the new Pendry Natirar with Ashley Douglass

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A few years ago, we had the pleasure of planning a beautiful wedding at the Natirar Mansion. So, needless to say, it was such a joy to return and meet the incredible new Pendry team now overseeing this stunning property—right in New York City's backyard.

Let me count the ways we loved every moment of planning this one! Alie and Michael were a dream couple to work with, and her parents, who were involved throughout the process, were just as wonderful.

Alie is one impressive woman—sharp, driven, and genuinely kind. With an MBA from Harvard, she’s passionately committed to advancing genetics to help prevent health issues like cancer before they begin. We were so inspired by her work and felt honored to have such thoughtful, brilliant humans as clients. I genuinely looked forward to every meeting, whether in person or over Zoom.

Recently, I had the chance to visit and stay overnight at the new Pendry—and shout out to the GM for the Penthouse upgrade!

I’ll admit it: I’m a total sucker for a resort with a five-star spa. The Pendry Spa absolutely delivered—spa, gym, and cuisine were all next level.

The main event space remains unchanged—still sun-drenched, modern, and welcoming. On the hotel side, new additions provide fresh options for weekend events, wedding celebrations, or full property buyouts.

One of my favorite new spaces is the large outdoor terrace on the top floor, just off a long, elegant dining room. The views stretch across the grounds and trees—it truly feels like you’re in another world. The terrace is a blank canvas, ready to be transformed with umbrellas, florals, and any décor your heart desires.

There’s also a lower terrace off the new restaurant, Ladd’s Tavern—perfect for a cocktail-style reception or a sit-down dinner. And if you're not doing a full buyout, you can reserve the acclaimed Ninety Acres restaurant for an event. Even better, host a cooking class there for your guests during the day or plan an intimate welcome dinner the night before the big celebration.

We’d be thrilled to bring a new client here for a 2026 or 2027 celebration. In the meantime, treat yourself to a visit at this incredible spa—complete with steam rooms, infrared saunas, a salt cave, and a range of luxurious treatments. Then, top it all off with a delicious meal at Ladd’s Tavern or Ninety Acres.

Until next time...

Happy planning,
Ashley

Photography by Allan Zepeda

The Biltmore to The Dunlin: An Epic wedding story!

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We will forever remember Rebekah & Ben’s wedding dearly. From day one, we knew it would be a notable weekend of celebration.  We often have repeat clients and familiar faces in attendance at our weddings, but it is not every day that we have upwards of three past couples and a few future clients as well.  This crowd has become like family, and stepping into the role of event planner doesn't feel like work at all. 

This planning began with a hip, wintertime engagement party at The Wooley on Broome Street. Classy, festive and totally relaxed, the couple's two worlds got to party with one another for the first time. Rebekah from Nebraska and Ben from Manhattan. 

Photography by Jenny Fu

Later in the Summer we also had the pleasure of planning a casual, summertime, backyard couple’s shower at Greene’s residence in New Jersey. By the time, the wedding month came around everyone know everyone and, oh, so fun that we got to spend time with multiple past clients and catch up! 

Life threw us all a curve ball when it decided to send Hurricane Helene to Asheville, NC, just weeks before their wedding.  I knew within a day or two that there was no way we could host at the historic Biltmore Estate.  Their classy, black-tie, Gatsby-esque wedding would have to move to another location.  I also knew this couple wanted to move forward with their lives rather than postpone. Prior experience has taught me that time is of the essence, especially when looking to move a wedding over a popular date. We secretly began planning a new weekend of celebration, in a new city, while they waited with baited breath, reluctant to give up hope that the water would recede in Asheville. .

We gave R+B many domestic and international choices, aiming to capture that historic feel.  None did the job. I know what they needed was a resort and less busy weekend than was originally planned. To arrive, check in, chill and then celebrate. I also insisted on a great team to execute since we would be meeting them literally 19 days prior to the wedding. 

About 3 weeks after Hurricane Helen Ashley had a list of venues but knew who the winner would be. For one, the couple already frequented Charleston, they are foodies, and many guests were coming from NYC and Charleston is one of the easiest and quickest domestic locations to travel to from here.

When you hire a wedding planner as clued in as Ashley Douglass Events, you get the added security of knowing having a hard pivot is not our first Rodeo. Additionally, because of our place in the industry we knew that the brand new Auberge Resort in South Carolina just opened, maybe all of one week before Hurricane Helen hit in North Carolina. 

With a wave of a wand, and a ton of working into the late-late night, as you can see, everything came together beautifully! Rebekah, Ben and their families and friends enjoyed a perfect weekend wedding at the brand-new Auberge Resort, The Dunlin, on John’s Island in Charleston, SC. 

We fit the previous design to suit The Dunlin’s event barns.  We had to change some of the decor but overall the aesthetics were similar minus that historical feel.  Perhaps the biggest lift was both helping some of the guests with the change in their own plans and attempting to keep the design almost the same in a busy climate with many rentals having been destroyed on one hand or already contracted out on the other.  

Sending love and hope that all necessary aid is given to Asheville as their rebuilding will be a long haul. This city was so kind to us and their people so approachable. We look forward to planning at the Historical Biltmore Estate again. 

Shout out to our new besties in the business - Social Spool and Technical Event.  They worked tirelessly. Thank you to Curated Events, Event Works, Emerson James, BBJ, and Nuage Designs for your time and patience.  Without these rental companies going above and beyond and pulling rentals from multiple regions, cutting new fabrics, and dealing with a less-than-perfect revised production schedule, none of this would have been possible.  

Shout out and thank you to the Lowland in downtown CHS which hosted our large welcome party in their cool restaurant/ townhouse, and brick courtyard. One of the many tasks needed to be accomplished to change the city let alone the venue, was to find a restaurant willing to close down on a Friday evening. We emailed, called and stopped in on foot, if not harassed, upwards of 30 restaurants unless we found the perfect location that was willing to shutdown for us to enjoy cocktails and many heartfelt speeches. 

Lastly, the hugest, heartfelt thanks to the truly caring and passionate Dunlin Team.  You have quickly become a new venue that is like family. We cannot wait to be back next year. 

Part of my heart will always be with Asheville and we intend to visit again soon. The vendors and staff at the various venues we had on the schedule for that weekend, including but not limited to hiking excursions in the Blue Ridge Mountains, will stay in memory. The kindness, the vulnerability, the strength. We are all in this together. 

Mazel Tov Rebekah & Ben

All photography by Jenny Fu