After planning and photographing more than 75 surprse proposals, we get asked a LOT, “what are the best surprise proposal locations in Charlottesville?” So in order to make things easier for our clients, we’ve settled on these 10 best locations to propose in Charlottesville, VA! Anyone who’s ever spent time in the Charlottesville area knows how much natural beauty there is here. And no one knows better than us how incredible this area is as a backdrop for your engagement! Of course, our couples are always the subject and main focus of our photography, but a gorgeous backdrop certainly never hurt.

 

We know that with dozens (maybe even hundreds) of options to choose from, narrowing things down to find the perfect location for your surprise proposal can be a challenge. So let us help! We’ve photographed at dozens of locations in central Virginia. But over the years, we’ve narrowed in on just 10 locations as our absolute favorites, specifically for porposals. So in no particular order, here’s our list of the best Best Surprise Proposal Locations locations in Charlottesville.

 

 

1. UVA: The Rotunda, The Lawn, and Gardens

If you have any connection to the University of Virginia, we don’t have to tell you how special the Lawn is. Like all the other public options, it can sometimes be a bit crowded, depending on the time of day and time of year. This is specially true while students are in town late-August through early-December and late-January through late-May. But that hasn’t stopped it from being our all-time most popular surprise proposal location! This is especially true when couples who met at UVa return to Charlottesville to get engaged!

 

 

The good news is that even in the busiest of seasons, the gardens can lend some privacy to your surprise engagement! And since the entire Lawn and the Rotunda is open to the public, it’s another location that’s easy to schedule any time of year. Since lots of the focus is architectural, it’s one of the few backdrops that’s just as striking during the winter, when trees are more bare. Or even during a snowstorm!

 

Want to see more Engagement Sessions from UVA and the Lawn?

• Cole and Grace’s Summer Surprise Proposal at UVa’s Gardens
• Rachel and Max’s Windy Spring UVA Engagement Session

 

2. Boar’s Head Resort

Boar’s Head Resort is another Charlottesville outdoor location that’s easy and convenient for photoshoots… or for dining and staying the weekend! Since there’s a hotel, restaurant, spa, and walking trails on site, our clients find it pretty easy to convince their partner to visit the Boar’s Head without raising suspicion ahead of their engagement.

 

 

Along with the classic open-field vibe found in many of our other sessions, there’s also fields of tall grass and water features to add a little something extra to your proposal photos. Because of all of this, Boar’s Head has always been one of the best surprise proposal locations in Charlottesville!

 

Want to see more Engagement Sessions from Boar’s Head Resort?

• Emily and Sid’s Wintery Surprise Proposal at the Boar’s Head
• Casey and Hannah’s Winter Engagement at the Boar’s Head Resort

 

3. King Family Vineyards

King Family Vineyards likely needs no introduction. Not only is it one of our favorite wedding venues in the area, but it’s one of the first places we bring friends for a glass of wine or Polo Sunday when visiting Charlottesville! When it comes to your engagement, if you’ve dreamed of getting engaged in a wide-open field as a golden sunset settles over the Blue Ridge Mountains behind you, King Family Vineyards might just be for you.

 

 

One consideration with King Family is that it’s a very popular spot for winerygoers at all hours of the day, and all year long! So if privacy is a high priority, KFV may not be for you. But if you like the idea of a crowd of strangers erupting into raucaus applause for you after you get engaged, then this is your place! King Family is another great location for a post-proposal celebration with friends and family, which we can also photograph for you!

 

Want to see more Engagement Sessions from King Family Vineyards?

• Pat and Khaliyah’s Double Surprise Proposal at King Family Vineyards
• Eesha and Patrick’s Giggly King Family (and Downtown Mall) Engagement Session
• Devon and Samantha’s King Family Vineyards Surprise Proposal

 

4. Hazy Mountain Vineyard and Brewery

Just outside of Charlottesville, one of the newest wedding and tasting room operations is Hazy Mountain Vineyard and Brewery. With great food and drink, and stunning views, it’s hard to go wrong for a casual weekend outing… that turns into a surprise proposal!

 

 

Like other vineyards, it’s easy to have friends and family hiding on property before you arrive. That way, once you’ve made the big ask (and they’ve said, “YES!”), you can keep the surprises rolling!

 

Want to see more from a Real Proposal at Hazy Mountain?

• Stephanie and Anna Grace’s Double-Proposal at Hazy Mountain Vineyards

 

5. Carter Mountain Apple Orchard

Carter Mountain Apple Orchard is another iconic Charlottesville location. However, many people know it for the pick-your-own apples, or their Summer Sunset Concert Series. What fewer people know it for is as an amazing surprise proposal location! Especially in the fall, it can be a very popular tourist destination, so privacy isn’t guarenteed. But Sarah and I are typically able to scout out a section of the orchard that’s closed to picking but open for photos, eeking out a bit of privacy for our clients!

 

 

If you want a more verdent engagement (or just like the idea of grabbing a fresh Bold Rock hard cider once you’ve popped the question), consider Carter Mountain. You could also consider it’s sister orchard, Chiles Peach Orchard, especially when the peach blossoms bloom in Spring! The only thing to keep in mind is that fall weekends are now ticketed at CMAO, so we’ll want to make sure we reserve our tickets well in advance!

 

Want to see more Engagement Photos from Carter Mountain Apple Orchard?

• Treslyn and Connor’s Sunny Surprise Proposal at Carter Mountain Orchard
• Lauren and Chris’s Apple-Picking Engagement Session at Carter Mountain Apple Orchard

 

6. Waterperry Farm

This private residence located about 15 miles outside of town is a true gem. With acres of classic European gardens, water features, a greenhouse, rolling hills, and mountain views, it’s as beautiful as it is versatile. If you really fall in love with it, you can even stay on-property for a night or two to really make your proposal special.

 

 

Although the owners of the residence ask for a rental fee to rent the space for a session, we think that it is absolutely worth it! Our favorite part about Waterperry is how incredibly accommodating they are when it comes to sessions, and we’ve developed a great relationship with the owners over the years. During most of our sessions at Waterperry, we have the entire property to ourselves, making your proposal both private, and spectacular!

 

Want to see more Surprise Proposals from Waterperry Farm?

• Olivia Claire and Isaiah’s Summer Surprise Proposal at Waterperry Farm and Gardens
• Chris and Kayla’s Wintery Waterperry Farm Surprise Proposal

 

7. Trump Winery

With its rolling hills of vines, adorable chapel, and wide vistas, Trump Winery can make a great backdrop for your surprise proposal! There are multiple locations on property that lend themselves to photos, so you’ve got plenty of options when you make the big ask. Plus, winerygoers will gather at the top of the hill at the tasting room, meaning proposals here are typically secluded and private. Just be aware that we’ll be constrained by their business hours, and can’t interfere with a wedding if they have one scheduled.

 

 

Another benefit to getting engaged at a public winery like Trump Winery is its potential for what Sarah and I call the “second surprise”! Once we’ve photographed your proposal, and a portrait mini-session, we can head up to the tasting room ahead of you, and capture your partner’s reaction as they realize that all their friends and family are on property, waiting to celebrate you two!

 

Want to see more Surprise Proposals from Trump Winery?

• Brittany and James’ Fall Surprise Proposal at Albemarle Estate
• Alec and Kaylee’s Double-Surprise Proposal at Trump Winery

 

8. Swannanoa Palace

Nearly 100 years ago, Swannanoa Palace was the closest thing that Virginia had to an Italian Villa! Although close inspection shows that the years haven’t been kind to the estate, it’s still open for photoshoots by appointment. While they also ask for a rental fee to shoot on the grounds, rest assured that your session fee is going toward maintaining this once-glorious property!

 

 

That being said, if you’re envisioning dramatic views and breathtaking architecture for your surprise proposal, this location about 30 minutes from Charlottesville might be perfect. And if you’re really looking for something unique (and are willing to double the rental fee), they’ll allow us to shoot inside, which makes for some incredibly dramatic imagery. This also makes Swannanoa a great proposal option during winter sessions or if you’re worried about a rain plan!

 

Want to see more Proposals and Engagement Images from Swannanoa Palace?

• Waseem and Sarah’s Stunning Outdoor AND Indoor Swannanoa Engagement Session
• Bri and Quinn’s Joyful Winter Surprise Proposal at Swannanoa Palace

 

9. The Blue Ridge Parkway (Raven’s Roost, etc.)

Most people think of Shenandoah National Park when they think of the mountains outside of Charlottesville. But there are some other stellar locations along the Blue Ridge Parkway that don’t require entering the Park! Raven’s Roost Overlook is the most popular location, with a more rugged and adventurous vibe. However, its convenience can be its downfall. It’s an incredibly popular spot to watch and photograph the sunset, so we often have to work around groups of people. As well as other photographers photographing portrait sessions! If privacy for your proposal is a priority, we don’t recommend weekend proposals here for this reason. That’s especially true in April, May, September and October!

 

However, reach out to us to learn of some other beautiful overlooks that could serve as the perfect backdrop to your proposal! We know of one overlook in particular that is almost always private and empty. But no matter where you are on the Blue Ridge Parkway, the natural beauty and panoramic views make for some very romantic-yet-outdoorsy proposal photos.

 

Want to see more Sessions from the Blue Ridge Parkway?

• Ken and T’Keyah’s Overcast Blue Ridge Parkway Proposal
• Lilah and Alex’s Casual Blue Ridge Parkway Engagement

 

10. Keswick Hall

Keswick Hall is the epitome of upscale accomodations and dining, and is only a 15-minute drive from downtown Charlottesville. If you’re looking to make not just the proposal, but the entire weekend memorable, book a room at Keswick Hall, and maybe even a reservation at Marigold or a couple’s massage at the spa!

 

 

But when it comes to the proposal itself, the architecture, rolling hills, and wide open spaces make for an amazing backdrop. Just reach out to us well in advance, as we do need to coordinate with their team for a proposal at Keswick Hall!

 

Want to see more imagery from a surprise proposal at Keswick Hall?

• • Madison and Hunter’s January Surprise Engagement at Keswick Hall

 

Bonus Location: Your Next Vacation!

This 11th location is sort of cheating, because we don’t know what your next vacation is! But we’ve flown all over the US to capture proposals and engagement sessions.

 

 

If you’re planning to propose on your next big trip, and can’t imagine anyone but us being there to capture it, just reach out to us! We can put together a custom travel quote.

 

Want to see more engagement photos from our travel portfolio?

• Ashlee and Mike’s Golden Engagement Session in Jacksonville, Florida
• Evan and Shannon’s San Diego, CA Surprise Proposal at Torrey Pines Natural Reserve
• Tanner and Jess’ Faux Engagement Session Turned Surprise Proposal in Corolla, North Carolina

 

What’s Next?

Let us know if you have any questions about any of our best surprise proposal locations in Charlottesville. Or, if you’d like to talk with us about scheduling your own surprise proposal, click here to learn more about our surprise proposal services and everything we offer!

 

 

Thanks for reading 😊