Most couples tour three or four venues, fall for one, and sign. Then the real questions surface, usually around month four, when someone asks who is actually setting the tables. A bride told us her favorite part of planning here was that our coordinator kept raising points she and her partner never would have thought to ask about. So here is our attempt to hand you those questions early, with our own answers attached. Ask them anywhere you tour.
Before booking a wedding venue, ask what the package includes, how long you can use the property, and who coordinates the event. Confirm catering options, menu flexibility, guest capacity, overnight accommodations, transportation, and outside vendor policies. Getting clear answers about included services, additional costs, and planning support helps couples avoid surprises and choose the right venue.
The Questions Couples Wish They'd Asked Sooner
None of these are trick questions. They decide whether your planning year is calm or frantic, and most of them have nothing to do with how a room looks on a Saturday in June.
What is actually included, and what will I be renting?
Ask for the list in writing, then look for the boring items. Chairs, linens, glassware, and flatware are where budgets quietly leak. Here, your date includes 10 farm tables and 14 round 72 inch tables, wood cross back chairs with cushions, and all linens, tableware, and glassware. The ceremony comes with chairs, an arbor, and a wireless PA system, so nobody has to hold a phone up to a speaker during your vows.
How much time do we get on the property?
A venue that gives you six hours on a Saturday is a different animal from one that gives you the weekend. At The Preston Barn, our weddings run as a full buyout, Friday at 3 PM through Sunday at 11 AM, with exclusive use of the barn and grounds, setup available the day before, and cleanup the day after. That changes the texture of the whole weekend. One couple told us their favorite part was having friends and family wandering the grounds while they set up, which only happens when nobody is waiting on a room to turn over.
Who runs the day, and when do they start?
Ask whether the venue's coordinator joins you at booking or shows up the week of. Ours works with you from your first site visit through the end of your event, and the coordinator is part of what's included with a wedding here. In practice, that means your floor plan and seating layout get coordinated here, your rehearsal is guided the evening before, and the day itself has someone whose only job is knowing what happens next.
How does the food work, and can it flex?
Ask who cooks, where they cook, and how much you can change. All food and beverage for barn events is handled in house by Old Drovers Inn out of our commercial kitchen. You can serve buffet, family style, or plated, and our chef will customize the menu, including around dietary needs. One couple who chose the buffet told us their guests gave the food high marks across the board.
Where do our guests sleep, and how do they get here?
If your family is travelling, this question saves you more stress than almost any other. At The Preston Barn, we offer six lodging options for your wedding weekend, each booked at its own rate. Old Drovers Inn has six guest rooms, each with a private bath and complimentary breakfast, and the Carriage House across the street has seven bedrooms and also includes breakfast at the Inn, bringing the total to 13 bedrooms on site. Lake Ellis Lodge offers 12 bedrooms, each with its own bath, giving larger families room to stay together, and Preston House, the seasonal Farm House, and Mountain Cabin round out the options. One couple described having friends and family stay on site and eating breakfast together with everyone the next morning as one of the best parts of the weekend.
Conclusion
A venue tour is a sales conversation, and that's fine, but the questions above turn it into a useful one. Ask what's included and what you'll be renting. Ask how long the property is yours. Ask when the coordinator actually starts. Ask who cooks and how much you can change. Ask where your guests sleep and how they'll get there. Ask what happens with your own vendors. The answers will tell you more about your planning year than any photo gallery will. We'd rather you arrive here already knowing what to ask, because the couples who do tend to make a decision they feel calm about, whether or not that decision is us.
Take this list to your next tour, including ours. Clear answers help couples understand whether a venue matches their needs. Contact us or call us at 845-442-3053 or email helene.rosenkranz@olddroversinn.com and we'll walk you through the barn and answer all honestly, including the parts we don't do.
FAQs
What is included with a wedding at The Preston Barn?
Exclusive use of the barn and grounds for the weekend, 10 farm tables and 14 round 72 inch tables, wood cross back chairs with cushions, all linens, tableware, and glassware, an on site ceremony with chairs and arbor, a wireless PA system, use of the stone patio, tent, sound system, and TV, an on site coordinator throughout planning and on the day, and a list of trusted wedding professionals. In house catering is available.
When does the on site coordinator get involved?
From your first site visit through the end of your event. The coordinator is listed among what's included with a wedding here.
How long is the weekend buyout?
Friday at 3 PM to Sunday at 11 AM, with the barn available for setup the day before and cleanup the day after.
How many guests can the barn seat?
Up to 220, with room for a dance floor and a band or DJ.
Is there lodging on site?
Yes. We offer six lodging options, each booked at its own rate. Old Drovers Inn has six guest rooms, each with a private bath and complimentary breakfast. The Carriage House across the street has seven bedrooms and includes breakfast at the Inn, for a total of 13 bedrooms on site. Lake Ellis Lodge offers 12 bedrooms, each with its own bath, and Preston House, the Farm House, and the Mountain Cabin are also available.
How do guests get there without driving?
We're five minutes from either the Harlem Valley/Wingdale station or the Dover Plains station on the Metro North line. A Suburban SUV shuttle is available at a fee for guests in off site lodging, and a six person golf cart with a driver is available during the event at an additional cost.

