One day just isn’t enough to celebrate a love like yours!

More and more couples are dreaming of a full weekend wedding, where all or a selected amount of their wedding guests can spend an entire three days together at a worthwhile destination. They want to make their wedding a whole experience and create more memories beyond a 5-6 hour event… and we are here for it! 

In fact, we have based our entire structure for our wedding venue services around this idea. Our venue, The Preston Barn in Dover Plains, is a beautiful newly-constructed barn with rustic charm and modern amenities on 7-acres of property that includes multiple outdoors areas for use, on-site accommodations, in-house catering, multiple dining areas, and plenty of fun unique things to do in the area. We can host pre and post-wedding events and only host one wedding per weekend so that you have us and the property all to yourselves!

But enough about us, you can check out more on that later. Let’s talk about how to plan and execute a fun and practical upstate weekend wedding itinerary your guests will look forward to and rave about for years to come! We’re answering lots of questions… What activities should be included? Who should be invited? How do you communicate the itinerary? If you are a New York City couple just starting to plan your upstate wedding, check out our other blog first: The New York City Couple’s Guide To An Unbelievable Upstate Weekend Wedding

DAY ONE.

Ceremony Rehearsal

We highly recommend doing a ceremony rehearsal. This should only be the wedding party and anyone included in the ceremony. Your officiant or wedding coordinator will provide guidance to make sure everyone knows what to do and where to go. This should probably happen first before all other weekend events. 

Welcome Party vs. Rehearsal Dinner

Everybody’s gotta eat! Typically after the rehearsal comes a rehearsal dinner. How that looks and who is invited is up to you! Generally, these are some of the options:

• Small intimate dinner party with wedding party, parents, other VIPs, and sometimes out-of-town guests

• Larger dinner party that includes more or all guests

• A more casual welcome party that includes a special list or everyone invited to the wedding
  

So how do you choose which is right for you? There are a few things to think about here…

If you have a lot of out-of-town guests, a welcome party might be a better option for you. This allows guests to meet and mingle more before the wedding day and spend more time with their favorite couple…YOU! Facing the facts, a 5-6 hour event where you are the center of attention and time flies by is not enough time to spend with every guest. A welcome party is a great opportunity to get some more quality time with everybody, whether they are visiting from afar or not. 

Here is some fun welcome party ideas:

• Use other areas of your wedding venue or use a nearby facility

• Bring in food trucks or do a casual BBQ-style event

• Lawn games

• Do a fun local activity (more on that coming up…)

If you’d like something more intimate for just your most special friends and family, go with a rehearsal dinner. It also could be a more budget-friendly option if you are splurging on the wedding day.

Another idea is to combine these two types of events. You could have a smaller rehearsal dinner with your VIPs while other guests can check out local eateries on their own, then meet up for a welcome party by your venue’s fire pit for s’mores, at a local bar, or ice cream parlor! (We have a great little ice cream place near our venue with a beautiful seating area and mini-golf! The link is towards the end of this blog so keep reading). 

DAY TWO: The Wedding Day

Breakfast/Morning of

Here at the barn, we offer breakfast to all of our guests staying on-site. We suggest keeping it minimal on the wedding day as far as activities for ALL guests. You’ll be busy getting ready! So what do those guests do all day while you and the wedding party are getting ready for the big event?

Provide suggestions for guests to get food, things to do, and places to explore in the area. If it is an area you frequent, share your favorite spots as a couple or ask your venue coordinator what the most popular/loved spots are. Think about what your guests enjoy or perhaps things they don’t usually get to do where they come from. Our couples from NYC love to share sightseeing opportunities like our local hiking trails. 

The After-Party

If you or your guests are the types who don’t want the party to end, then keep it going! Does your venue offer an after-party? Would you want it open to everyone or just a selection of your guests? Here are some ideas:

• If your venue offers something on-site, this is always great. Easy and safe.  

• Firepit and/or a food truck for late-night snacking

• Go to a local club or bar (PROVIDE TRANSPORTATION)

DAY THREE

Send-off Brunch

There’s nothing better than a great breakfast (and a mimosa!) the day after a wedding. Our venue provides the option to do this on-site. Again, if many guests are from out-of-town, we suggest making it a bigger, more casual event to include everyone staying the weekend. 

Whether it is a small and intimate or a larger affair, this is a great opportunity to reminisce with everyone about the great time they had at your wedding and share the memories made. You can spend time with anyone you haven’t had the chance to and say goodbye to those heading back to a destination farther away. 

Then again….why stop there? We have a whole day! 

HAVE More Fun!

Fun things to do and explore in the area will most likely come on the day after the wedding but can also be done on day one, or the guests can do that in their free time on day two as well. These ideas below are based on what we have here in/near Dover Plains, but can inspire ideas for any venue you choose:

• Visit local trails and gorgeous views (Dover Stone Church, Appalachian Trail, Innisfree Garden, Kent Waterfalls, Mid-Hudson Rail Trails, Nellie Hill Preserve)

• Visit local Wineries and Distilleries (Millbrook Vineyard, Cascade Mountain Winery, Clinton Corners Winery, Taconic Distillery, Hillrock Distillery, Tenmile Distillery)

• Visit Wings Castle, Crown Maple Syrup Estate, Soukup Farmers Market, Millbrook Farmers Market, Millbrook Antique Mall

• Four Brothers Inn and Drive-In Movie Theatre

• Mini Golf and Ice Cream at Kelly's Creamery (they also have a tented area with fire pits and seats. A great spot to hang out after rehearsal dinner!)

• Trevor Zoo at Millbrook School

• Local Carnivals and Fairs (summer)

• Local Farms (in the fall there’s great apple and pumpkin picking, events, and amazing cider donuts!)
  
  
  

More tips….

How to communicate the itinerary

• Within the invitation suite. If all guests are included with mostly every event, add it right in with the invitation suite so that they can plan their trip accordingly.

• In the welcome bags. Let your weekend guests know what is going on and when and these are a great place to add your suggestions for local food and activities. Check out our blog about what to add to welcome bags!

• Have VIP only events? Add a cute ticket or token as your invite for those special guests to the invitation suite, welcome bag or distribute at rehearsal. 

Timing

Make sure there is enough time for travel, breaks, changing clothes, etc. between events. Consult with your planner or coordinator and any vendors involved since they’ve likely done this before and know the area well enough to consider travel time, traffic, and experience with past events. 

Choosing the right venue

Choosing a venue that can host all or most of these events and can provide on-site and nearby accommodations can be very helpful. There would be a lot less to coordinate and would likely save you so much time, frustration and money. If you agree, then we suggest you come check out our beautiful venue, perfect for the weekend wedding away from the city. Come see for yourself or contact us with your questions using the form below!

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