We cannot speak highly enough about this venue and the people you work with. My wife and I had were considering this without either of us having been there since our early teen years, which can be nerve wracking! The people in charge of events, Jason and Rachel, took that in stride and offered a video tour that really helped settle us and see what it could be.
The grounds are beautiful, with backdrops of the mountains in so many directions, and each section is wonderfully partitioned with box hedges. When you book, you get the entire space, which includes 2 potential outdoor ceremony sites, the garden right off of the house, access to the house for tours if you wish it, covered pavilion, and a barn that can function as another ceremony site/rain option. We had so many comments from guests about how stunning it all was!
Leading up to our wedding day, there was a potential for rain. Naturally, we both began worrying and reaching out to the venue, as well as panic buying umbrellas. Jason and Rachel were fantastic, reassuring us that they would help however possible, but also that they didn’t think the rain would hit until later in the night. Sure enough, we were lucky and the storm didn’t roll in until around 8, at which point most of our guests decided to dance in the rain and make the most of it! This venue truly is special, and we are beyond grateful that we found it.

This venue is one of the most beautiful wedding destinations in Charlottesville, and is easy to work with, while not breaking the bank! Emilia and the rest of the event staff at James Monroe's Highland are very responsive, helpful, and professional. I am a wedding planner and coordinator based out of Richmond, and it is crucial to have a supportive venue when making plans for clients. If you want a historic venue with gorgeous views at a great price, look no further!

Couldn't be happier with our choice of James Monroe's Highland!! If you aren't excited about the idea of having just another generic, impersonal Virginia winery wedding and are looking for a location with a long history, character, and beautiful scenery, you absolutely need to look into this venue. Highland is a special place. The Highland Events manager (Jason) was super helpful, professional, patient with all my questions, and so very personable -our favorite "vendor" of all. The price was surprisingly reasonable compared to other central Virginia outdoor venues, and a large chunk of it is a tax-deductible donation that goes toward funding Highland's education and preservation projects - it felt amazingly good to invest some of our wedding money in this way.
Having an outdoor wedding can be nerve-wracking due to the unpredictability of weather, but we got lucky for our late April wedding. They have a backup indoor space in case of very bad weather, but honestly, it would've been a huge disappointment had we had to move indoors. The historic grounds were green and gorgeous, with brick walkways and interesting spaces at every turn. The long driveway up with framing trees is an iconic location for bride-and-groom photos. The secluded ceremony area (the Blue Ridge yard) surrounded by boxwoods and a white fence was an intimate setting for our wedding of 70 (it would've fit dozens more and they have a larger space if needed), with lovely, peaceful scenery as the backdrop. A charming garden area was the cocktail hour space (where guests have the option of taking a brief walk through the indoor exhibit spaces which are literally right there), and then a covered hilltop outdoor pavilion was the reception area. Although it sounds confusing, all these places are just a few steps away from each other (less than a 2-minute walk). Things ran smoothly, there were zero glitches on the wedding day thanks to the friendly Highland staff, and we and our guests loved the setting. It was magical.