Starting your wedding planning journey is exciting. But knowing how to start wedding planning can feel overwhelming. Before you’ve even picked a date, there are endless ideas, checklists and decisions waiting. So how do you know where to begin?
One of the smartest ways to start wedding planning is by thinking through what really matters to you. Before diving into Pinterest boards or vendor research, take a moment to ask yourself a few key questions. These will help guide every decision ahead, including one of the biggest: choosing a wedding venue.
Here are five questions we encourage every couple to ask themselves early on.
1. What kind of experience do you want for your guests?
This one question can guide your entire approach. Do you picture a formal black-tie celebration or a relaxed evening outdoors? Do you want your guests to feel pampered, at ease, or like they’re on vacation?
Your answer will help define what kind of venue will best support that feeling. Some couples want a classic ballroom. Others prefer a private estate where guests can wander, mingle, and connect more casually.
At Windridge Estate, we believe guest experience is everything—and we’re proud to offer a space that meets you wherever your vision lands. We’ve hosted black-tie weddings with champagne towers and formal dinners, as well as barefoot ceremonies and cozy welcome parties around the firepit. With multiple gathering spaces, outdoor amenities and a welcoming atmosphere, Windridge has the range to do it all.
2. How long do you want the celebration to last?
When you start wedding planning, it’s easy to assume it all happens in a single day. But more and more couples are leaning into full weekend celebrations.
Think about whether you want one day of celebration or multiple opportunities to connect with your guests. A welcome dinner, after-party and post-wedding brunch can all become meaningful parts of your wedding story.
The venue you choose plays a big role in making that possible. Some places offer just a few hours, while others provide space to spread out and savor every moment. Each wedding at our estate offers full weekend access to give couples the time and flexibility to truly enjoy it all. From welcome drinks, setup, celebration and slow goodbyes, you’re never rushed and neither are your guests.
3. Do you want everything in one place—or spread out?
Some weddings require transportation from the hotel to the ceremony to the reception. That can add stress to either you or your guests and cut into time you could spend together.
Ask yourself: would you prefer a single location where everything happens in one place? A venue that offers both indoor and outdoor spaces, and even lodging?
Windridge Estate was designed with this in mind. We offer a seamless flow from ceremony to cocktail hour to reception. On-site lodging for up to 10 guests at the Farmer’s Cottage makes it even easier for those you want there for every moment. Couples love not having to think about transportation or logistics between their events.
4. How will your venue handle weather or rain plans?
Outdoor weddings can be stunning, but they require thoughtful weather planning. If you’re considering a venue with outdoor ceremony locations, it’s important to understand how they handle unexpected changes in the forecast.
Windridge offers several outdoor ceremony spaces and covered areas, along with clear backup plans for every scenario. We also have a beautiful space designed to accommodate a tented reception if you choose to bring one in. What matters most is flexibility and a solid plan. That’s how couples stay confident and guests stay comfortable, rain or shine.
From the Stone Wall to the White Barn and Belvedere Pavilion, Windridge gives you options. Whatever the weather brings, your day will feel seamless and beautiful.
5. How much support will help you feel confident?
Every couple has a different planning style. Some want hands-on help and detailed guidance. Others prefer more creative freedom with light-touch support.
It’s important to know what kind of help will make you feel relaxed and in control. That way, you can choose a venue team that fits your needs. Not one that overwhelms or underdelivers.
Couples at Windridge often say they feel seen and supported. We’re here to guide you, offer ideas and answer questions. But we also give you space to bring your unique vision to life.
“We want to express our deepest gratitude to Mary Beth and the entire team at Windridge Estates. Their expertise and guidance made the entire process seamless, and we felt confident that our wedding day was in the hands of dedicated professionals who genuinely care. It’s challenging to put into words just how amazing Mary Beth is. Her support went beyond what we could have imagined, and her kindness truly sets her apart. She is not just the venue owner; she’s a person who genuinely cares about making your wedding day the best it can be.” – Allie and Matt
Why These Questions Help You Know How to Start Wedding Planning
When you start wedding planning, it’s easy to get caught up in small details. But if you take time to answer these five questions, it will help you move forward with clarity.
They’ll help you spot the venues and vendors that align with your priorities. They’ll also help you avoid common planning pitfalls, like booking a venue that doesn’t fit your celebration style.
Choosing a wedding venue is one of the most impactful decisions you’ll make. It sets the tone for everything else. So the more intentional you are now, the smoother and more enjoyable the entire journey will be.
Ready to Take the Next Step?
If your answers reflect a desire for beauty, ease, flexibility, and time with your favorite people—Windridge Estate might be a perfect fit. We specialize in full weekend weddings with thoughtful service and unforgettable settings.
Explore our services or book a tour to start dreaming up your day.
And remember, how you start wedding planning matters. These early questions can help create the foundation for a wedding that truly feels like yours.
