Historic Downtown Date Night Photo session in Staunton, Virginia

When winter winds blow through the charming streets of Staunton, Virginia most folks stay inside. But not Meredith and Mateo! These two brave souls ventured out on the COLDEST evening of winter for what turned into one of the most fun date night photo sessions I’ve ever shot.

I grabbed some hot lattes on my way to meet them – and boy, did we need that warmth! Meredith looked stunning in her sweater and fur coat from Juniper Lane, the cutest little curated vintage boutique in Historic Downtown Staunton. Mateo matched her style perfectly in a dapper blazer also from Juniper Lane.

Armed with my two cameras, the three of us ran, danced, and laughed our way through the empty streets. The cold couldn’t stop us from capturing pure magic in this gorgeous historic town.

Want to see all their amazing photos? Check out Meredith and Mateo’s Staunton date night in my client gallery!

Exploring Staunton’s Historic Charm

We hit all the best spots in downtown Staunton. First, we admired the stunning architecture of the Old Clock building where the Cigar shop sits. Then we headed to the Visulite Cinema where stepping inside feels like traveling back in time with its vintage movie house charm.

Staunton has been getting lots of well-deserved attention lately, even being featured in Travel + Leisure’s guide to this charming Virginia town. It’s no wonder why – the brick buildings, unique shops, and friendly locals make it a perfect backdrop for couples photos.

In the parking garage, we got lucky and found an old classic car in perfect condition. It matched our vintage vibe so well that we had to snap some photos with it!

Sweet Treats and Warm Moments

When our noses turned red from the cold, we ducked into The Split Banana for a sweet break. If you’ve never been to this year-round gelato shop with its cute checkered floors and vintage style booths, add it to your must-visit list right now!

Even in winter, their treats hit the spot. The warm interior gave us a chance to thaw out our fingers while still capturing some cozy indoor shots.

Not to be cliché, but Meredith and Mateo truly brought the heat to an otherwise freezing evening. Their chemistry warmed up every frame, and their smiles never faded despite the chill.

Looking for ideas for your own photoshoot? View more engagement and couples sessions for your inspiration!

5 Tips for Planning Your Own Staunton Date Night Photoshoot

1. Dress for the Weather (But Make it Cute)

Meredith and Mateo nailed this by layering stylish pieces from Juniper Lane. In cold weather, think:

• Cute coats and jackets
• Scarves and gloves
• Boots that are both practical and stylish

2. Pick the Right Time of Day

For that golden hour glow:

• Schedule your shoot 1-2 hours before sunset
• On cold days, aim for midday when it’s warmest
• Empty streets make for better photos, so weekday evenings work well

3. Include Meaningful Stops

Make your session personal by visiting:

• Your favorite coffee shop or restaurant
• Places from your first date
• Spots that show off Staunton’s unique character

4. Bring Props and Comfort Items

Smart additions include:

• Hot drinks (they warm hands and make cute props)
• A small bag with touch-up supplies
• An extra layer you can add or remove

5. Trust Your Photographer’s Vision

Let me guide you to:

• The best light and angles
• Hidden gems in Staunton’s historic district
• Poses that feel natural and show your connection

Want more tips for your big day? Get a FREE copy of my Wedding Guide here!

Recommended Vendors for Your Staunton Date Night

These local businesses helped make Meredith and Mateo’s session special:

• Visulite Cinemas – A historic movie theater with tons of character
• The Split Banana – Delicious gelato in a vintage-inspired setting
• Juniper Lane – Curated vintage fashion perfect for photoshoots

Frequently Asked Questions

How long does a couples photoshoot in downtown Staunton typically take?

Most couples sessions last between 1-2 hours. This gives us time to visit several locations without you getting too tired or cold.

What if the weather is bad on our scheduled day?

Don’t worry! We can always reschedule if the forecast looks truly awful. That said, some of my most amazing shots (like Meredith and Mateo’s) happen in less-than-perfect weather!

Do you help with outfits and location planning?

Yes! I love helping couples plan their perfect session. From outfit choices to location scouting, I’m here to make sure you look and feel amazing. I provide a full outfit styling guide for this. 

Can we bring our dog to the photoshoot?

Absolutely! Furry friends are always welcome. Just let me know ahead of time so we can plan pet-friendly locations.

Is downtown Staunton, Virginia crowded for photos?

It depends on the day and time. Weekday evenings tend to be quieter, while weekend afternoons see more foot traffic. I know all the hidden spots where we can get amazing shots without crowds.

Ready for Your Own Historic Downtown Staunton Couple’s Photos?

I’d love to help you create beautiful memories in this charming Virginia town! Whether you’re celebrating an engagement, anniversary, or just your love story, Staunton’s historic streets make the perfect backdrop.

Don’t wait to book your session – prime dates fill up fast, especially during spring and fall. Contact me today to start planning your own unforgettable downtown Staunton couple’s photoshoot!