Your Stress-Free Planning Guide For Your Hudson Valley Wedding

So you’re engaged? Congratulations! Planning a wedding in the Hudson Valley can be overwhelming. We have so many great spaces, incredible food, lots of things to do in the area (for those coming from the city for a getaway), and endless amounts of talented wedding professionals to choose from. 

So how do you do it all without getting overwhelmed and stressed? Planning a wedding can always get stressful, but this is our guide to help you get started, and take your planning process one step at a time. Are you ready? Great! But first…

Allow us to introduce ourselves. The Preston Barn is a wedding and event venue in Dover Plains, NY (80 miles north of Manhattan) that caters to the weekend wedding. We can host your full weekend destination wedding from rehearsal dinner to the send-off brunch. We have accommodations on-site and nearby for up to 54 guests and on-site catering. With modern amenities, a ton of space, and a dedicated staff, we make wedding dreams come true. Learn more about our weddings here and contact us here for pricing and a tour!

Okay, let’s get to the good stuff…

Where To Begin 

The number one question. We know it’s tempting to go straight to Pinterest and look at centerpieces and hairstyles, but try your best to hold off. There are a few things you need to figure out first before you can choose your venue, vendors, and… all the pretty and fun things. In fact, we have a whole other blog about it! It’s called 5 Important Things to Know Before You Tour. But we’ll summarize it a bit for you…

  • Your Budget. You need at least an idea because there is no point in shopping for venues or dresses or decor until you know what is realistic. 

  • The Guest List. Again, you need at least an idea. This goes hand-in-hand with your budget. More Guests = More Money

  • The Date. If your date is flexible, you’ll need to at least know the year and season desired because of availability, how far ahead to book things, and knowing the type of venue that can accommodate. 

The other two fall into our next section…

Choose your Venue/Caterer

Unless you are working with a planner to find your venue, this is usually the first thing you should look for and book. Why? Because the venue and catering will make up close to or more than half of your budget. So once that is out of the way, you’ll know what else you can afford to do! Also, some venues book really far in advance, especially in the fall months. You need to book about 2 years in advance! Here are a couple of things you need to think about beforehand…

  • Type of Venue. Are you looking for indoors or outdoors? All-Inclusive or DIY? Will you need on-site accommodations? (Check out our blog: Choosing Wedding Venues: What are the most important questions to ask?)

  • Style of Venue. Okay, now you might want to poke around Pinterest a little bit. You’ll need an idea of the overall style and look you desire for your wedding day because the venue should match it.


Then what? Choose 3-5 venues to tour. Don’t overwhelm yourself with too many. We believe that when you visit your venue, meet the coordinator, and try to visualize your wedding day, you’ll know the right choice when you see it (at least that’s what so many of our couples say about us anyway)!

Choose your other vendors

If you are working with a planner and haven’t hired one yet by this step, now is the time. Both your venue and planner will have recommendations for other vendors. Why use their recommendations? We have a few reasons…

  • There are many to choose from. Save yourself the time and the overwhelm. 

  • They know who does the best work.

  • They will recommend professionals who suit YOUR style and needs.

  • They will recommend professionals that they work well together with. You can have the dream team!

FAQ: When should we start hiring vendors?

This depends on what type of vendor and when your wedding is. 

For winter months and even summer months, you may be able to book major vendors (Photographers, DJs) under 12 months but we recommend at least 12 months. For popular months like September and October, you’ll want to book 1-2 years in advance! All other vendors should be booked 8-12 months in advance. 

Now that we have the major steps out of the way, now you can start doing the stuff that is just a tad more fun, like choosing your decor, shopping for apparel, comparing hairstyles, etc. However, this is when things can get messy with so many options and details. Which brings us to…

Stay Organized

  • Grab a planning checklist. They are everywhere. But then recreate it, customizing it to YOUR needs. It will seem less like assigned work and more like your own thing.

  • Consider using a separate email just for your wedding stuff. We know how flooded inboxes can get so this will assure that you don’t miss anything and all communications are in one place!

  • Use fun tools like Trello or Google Sheets to keep all of your wedding plans and documents together and accessible from anywhere. They can also be easily shared with your planner and vendors this way. 

Our best tips for staying stress-free

  • Hire a planner or coordinator. Seriously. They are not the same as venue coordinators. Learn more about that here.

  • Don’t try to DIY everything. Some things are better left to the pros. Doing too much so close to the big day can end up being disastrous.

  • Trust your professionals. Don’t try to micromanage. As long as you have hired real, experienced wedding pros, they’ll make sure you’re taken care of. Choose wisely, and then LET GO. *insert sigh of relief*

  • Assign yourself NO TASKS on your wedding day other than getting ready and enjoying yourself. Make sure everything is taken care of for you, preferably by professionals and not your wedding party or your mom. They should enjoy the day WITH you.

To summarize, start with the biggest tasks. Then cruise along with the easier stuff. Doing too much too soon will only stress you out and waste precious time. Follow these steps and tips, and you’ll get to enjoy both your engagement and wedding day. 

If you are looking for a Hudson Valley wedding venue with rustic charm, modern amenities, accommodations, and amazing food, come take a tour here at the Preston Barn! We put a lot of work (and heart) into making the planning process as simple and stress-free as possible. We take pride in the fact that our past couples have a lot to say about that! See for yourself in our testimonials!

Planning a wedding during the Covid pandemic was very stressful but Helene went above and beyond to help us through it. Thank you so so much Helene! -Melissa

From the incredible staff, to the delicious food, to the most charming and romantic ambience, we wouldn’t change one thing. -Jaclyn

The Venue Coordinator… went above and beyond to make our day fantastic and to help mitigate a lot of the stress of planning our event. -Catherine

Our entire experience with The Preston Barn and Old Drovers Inn was truly outstanding! We cannot say it enough! I recommend this venue to anyone who is looking to have an incredible and customized experience in a gorgeous location with high-quality food and wonderful, attentive and caring people! -Erin


Contact us today to get more information and book a tour!


Like this post? Pin it!