Adventurous Hiking Engagement Session on Skyline Drive | Shenandoah National Park | Charlottesville Wedding Photographer

Vicki, Stephen and their pup enjoying the sunset at Little Stony Man hike on Skyline Drive of Shenandoah National Park.

One of the questions I get a lot for hiking engagement sessions is: “What do we wear if we’re going to have to hike into a summit?” The easy answer is — whatever you want. But since choosing to wear cute clothes to hike in is an easy way to do two outfits in your session, here are a few tips.

  1. DO choose footwear that is comfortable and functional. I do most of my summer hikes in Keen sandals, but that’s not comfortable for everyone. So instead consider hiking boots or cute tennis shoes. DON’T feel like you need to go out and buy hiking boots just for your session, though. If tennis shoes are your jam — wear them!

  2. DO pick clothes move well without and breathe well. For you that may mean leggings and an oversized sweater (my normal hiking attire) or it could mean technical pants and a vest purchased at L.L. Bean, REI or Eddie Bauer. DON’T go with the ratty t-shirt with three holes or those sweatpants from high school you are still amazed are still alive.

  3. DO pack layers. Weather in the mountains can change really fast. Even if it’s chilly when we park, odds are halfway to the summit you’ll need to shed a few. Some of the more popular summits in Shenandoah National Park and the Blue Ridge Mountains have a tendency to be really windy so depending on the summit and location, it can get get really cold when you get to the top (or feel amazing if it’s the middle of summer). So bring plenty of layers to shed or add.

When we get to where we’re going, we’ll usually take a few photos in whatever you hiked in. Then, we’ll set lookouts or you can hide in a bush and change into your other outfit. For guys that generally means a shirt change. For women, I recommend considering a flowy dress. Dresses are gorgeous against the mountains and catch in the wind well. Even if you change into a dress, though, wear sandals, flats, booties or go barefoot — NO heels. They are totally impractical for scrambling around wild spaces.

Finally — how do you keep hair/makeup nice on a hike? In the winter or early spring/late fall you generally won’t sweat much so it’s not a big issue. If we’re going on a long hike, consider using bobby pins to pin up hair. Bobby pins are a lot more forgiving than a ponytail band and are easy to remove when we summit. You’ll be running around a bit so embrace a bit of beach waves, wildness and mess.

As for makeup, if it’s the height of summer, I really recommend considering a sunrise session. Sunrise can be as much as 20 degrees cooler than later in the day and often less humid too. We can always bring a small mirror and makeup kit to touch you up before starting to shoot your engagement or elopement if need be!

For this Skyline Drive engagement session, Vicki and Stephen picked Little Stony Man — the first hike they’d done as a couple. The hike to this summit is relatively short, but can be combined into a 3.7 mile loop for a longer adventure. The longer hike includes another summit, which is one of my favorites in the park, but unfortunately one of the only summits in Shenandoah National Park that you are not allowed to bring dogs on. So when bringing your pup to your session, Little Stony Man is a better bet than Stony Man.

(Side note, Little Stony Man is also an awesome location for an afternoon elopement due to a few flat spots that could accommodate an officiant and small handful of witnesses.) It is, however, a very popular location due to how easily accessible it is, so if you want the space to yourself try hiking it on a weekday.