The New York City Couple’s Guide To An Unbelievable Upstate Weekend Wedding

You love New York. You thrive on the hustle and bustle of city life, the night life, your career, and the people you surround yourself with. This life is great! But for your wedding day, you’re looking for something new, something different…

Is this you?? 

As a Hudson Valley or “Upstate” wedding venue ourselves (learn more about us here), we’ve met many similar couples like you from Manhattan, Brooklyn, Queens, Staten Island and Long Island with their reasons for venturing upstate for their wedding day. Here are some that we have heard:

  • More open space

  • Less expensive 

  • Change of scenery

  • More unique venues (such as lovely barns! *wink*)

  • Things to do that can’t be done in the big city

Whatever your reason, planning a fun country getaway for your city-living friends and family can be challenging when you don’t live here. We have helped guide many couples just like you through the process so consider this informative blog a head start!

Quick intro…

We are The Preston Barn, located on the property of the historic and beautiful Old Drovers Inn. We are located just 80 miles North of NYC and sit on 11 acres of land just outside the Hamlet of Dover Plains. We are close to country settings with rural surroundings and country charm. With neighboring local wineries and hiking trails, it is the ideal venue for any event. With on-site and nearby accommodations and the ability to host pre and post-wedding events, it is especially great for couples looking to explore the area with their guests for an extraordinary weekend getaway. Learn more about us here.

And without further adieu, here is our advice for the New York City couple planning an Upstate New York wedding:

Consider hiring an expert. 

If you’ve seen our other blogs, you know we say this a lot. #sorrynotsorry

The Hudson Valley (and beyond) is loaded with amazing planners who work with city couples to create the picture-perfect event from finding the right venue to all the nitty-gritty details. They KNOW this area well, they know all the venue details, and they know which vendors would be right for you. A planner can narrow down the MANY options for you based on what YOU want for your wedding day or wedding weekend. 

Some planners offer venue scouting services separately. We love this idea! Not only can they help you narrow down the best venues for what you desire, but it also gives you a “test drive” of the planner’s expertise and you’ll know if you’d like to work with them some more.

Speaking of venue hunting…

Find a venue that has “all the things”.

We may be a little biased in this area, but finding a venue that has multiple spaces, includes a lot of things that you’d otherwise have to rent (tables, chairs, etc.), can host pre and post-wedding events, and has on-site accommodations, can be extremely helpful. Venues like this (*ahem* The Preston Barn) also often only hosts one wedding per weekend so you and your guests have the entire space to enjoy, all to yourselves! 


You might prefer a venue that is more customizable and raw so that you can have the freedom to create a whole new vision. We get it, that’s why we try to be as flexible as possible too. Our advice for this type of venue is to DEFINITELY hire a planner because you will need tons of rentals and design experts to help you bring that vision to life. You’ll also need a pretty big budget. 

It’s more than a wedding, it’s a whole weekend experience…

If you are looking to have a whole weekend itinerary, make sure your venue has accommodations on-site or nearby and some fun things to do in the area! Figuring out the activities you want to do will help aid your venue scouting too. Love to hike? Pick a venue with nearby trails to explore!

(We have a blog coming very soon with ideas of things to do around our venue and how to create an awesome itinerary for your weekend wedding. Follow us on Instagram to be in the know!)

Check out this other fantastic blog…

We recently shared a blog called “Your Stress-Free Planning Guide For Your Hudson Valley Wedding”. There are some great tips on where to begin on your planning journey, choosing your venue and vendors, and how to stay organized and stress-free. Check it out!



Other helpful blogs:

Choosing Wedding Venues: What are the MOST IMPORTANT questions to ask?

 The Best Months To Get Married In The Hudson Valley 

Wedding Venues: 5 Important Things To Know Before You Tour



Ready to start touring and want to begin with a unique and dreamy barn that has it all? Come take a private tour with us! You can even have dinner at our on-site restaurant and get a preview of our talented chefs and staff! 




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