Jessica Underwood Photography

Jessica Underwood Photography Southern Maryland based photographer documenting weddings, families & milestones with warmth and inclusivity. All are welcome here. 🌈🤍📸

Wedding Packages starting at $3800

Portraits starting at $275

Home is more than a place....it's where life's sweetest moments unfold 💕 🏠 This beautiful family is settling into a new...
06/11/2026

Home is more than a place....it's where life's sweetest moments unfold 💕 🏠

This beautiful family is settling into a new home and soaking up every moment with their precious baby girl. From first homes to first milestones, it's such an honor to capture the memories that make this season of life so special.

Congratulations on your beautiful home, your sweet little one, and all the memories still to come.


Some wedding days feel especially meaningful, and Kassidy & Dale's was one of them.Throughout the day I found myself sur...
06/11/2026

Some wedding days feel especially meaningful, and Kassidy & Dale's was one of them.

Throughout the day I found myself surrounded by familiar faces, watching people I've photographed through different seasons of life come together to celebrate. Being trusted to capture another milestone for a family that has supported my business for so long is something I never take for granted.

From the beautiful setting at Bowles Farms to the heartfelt moments shared with family and friends, this day was full of love, laughter, and so many memories worth preserving. It was such an honor to document Kassidy's marriage to Dale and witness the beginning of their next chapter together.

Congratulations, Kassidy & Dale! Thank you for allowing me to be part of such a special day. ❤️

Vendor Team

Venue: Bowles Farms
Coordinator: Nancy Bowles Wallace
Videography:
Florals: Weavers
DJ: CJ the DJ Cj Dickerson
Hair & Makeup: Brooke Bowles & Team
Bridal Gown: Serendipity Bridal
Tuxedos: Generation Tux
Photography: Jessica Underwood Photography

Johnna & Ben 💕 What a beautiful day celebrating these two at Jubilee Farm & Vineyard surrounded by their favorite people...
06/09/2026

Johnna & Ben 💕

What a beautiful day celebrating these two at Jubilee Farm & Vineyard surrounded by their favorite people. From the waterfront ceremony to the laughter shared throughout the evening, every part of their wedding reflected the love and joy that brought them here.

After meeting through a university climbing club and building a relationship that spanned states, their journey led to this unforgettable day filled with family, friendship, and a whole lot of happiness.

Congratulations, Johna & Ben! Thank you for trusting me to capture these memories. Wishing you both a lifetime of adventures together.

Venue:

Coordinator: Maggie
Catering
Florals: Weavers
Cake: Sarah Lane
DJ: Ernie with Invincible Entertainment
Hair & Makeup: Julia O'Connell
Photography: Jessica Underwood Photography

A little preview from this beautiful maternity session.This mama is absolutely glowing ❤️
06/07/2026

A little preview from this beautiful maternity session.

This mama is absolutely glowing ❤️

There is something especially meaningful about being trusted by another photographer to capture their family. Someone wh...
06/04/2026

There is something especially meaningful about being trusted by another photographer to capture their family. Someone who understands the value of photographs, appreciates the little details, and spends their own days preserving memories for others choosing you is truly one of the highest compliments.

Jessica and her family were an absolute dream to photograph. From their beautifully coordinated outfits to the genuine smiles, laughter, and connection they shared, every moment felt effortless and full of love.

Being trusted with memories that can never be recreated is a privilege I never take for granted, and I am so grateful to have documented this beautiful season for their family. 💕

Goldpetal Farms Maryland

Stepping into Rose Point feels like walking straight into the pages of a storybook. Surrounded by blooming roses, windin...
06/01/2026

Stepping into Rose Point feels like walking straight into the pages of a storybook. Surrounded by blooming roses, winding garden paths, and the soft glow of golden hour, every moment feels a little more magical.

If you've ever dreamed of photos that feel like a fairy tale, this is the place.

Congratulations on your engagement Mary & Tyler!

You can book your next session here!

📍 Rose Point Waterfront Garden Estate

📸 Jessica Underwood Photography

🌹✨💕

Booking fanily sessions at Goldpetal Farms Maryland Shoot me a message to get on the books!
05/24/2026

Booking fanily sessions at Goldpetal Farms Maryland Shoot me a message to get on the books!

Some sessions just feel effortless The kind where the laughter is real, the love is easy, and the joy between two people...
05/22/2026

Some sessions just feel effortless

The kind where the laughter is real, the love is easy, and the joy between two people is impossible to miss. These two were SO much fun to photograph, completely themselves the entire session, and their genuine happiness made every image come alive!

And of course… bringing their pups along made it even better 🐾

I’m obsessed with the soft beachy vibes, the barefoot walks through the water, and all the candid moments in between. Sessions like this are exactly why I love what I do.

From high school sweethearts to husband and wife ❤️ Tori & Ben’s wedding day was full of the kind of moments that matter...
05/21/2026

From high school sweethearts to husband and wife ❤️

Tori & Ben’s wedding day was full of the kind of moments that matter most! Surrounded by the people who have loved them through every stage of life. All on their family’s private farm made the day feel even more meaningful and personal.

Congratulations Mr. & Mrs. Fowler! Thank you for letting me be part of such an incredible day!

Vendor Team ✨

Coordinator: Kara &KCoordination
Videographer: Holland Videography
Florals: Weavers
Catering:
Cake:
DJ: Invincible Entertainment
Hair: Beautybybrooke
Makeup: Kylie Nicole
Bridal Boutique: Champagne Taste Bridal Boutique
Decor: Something Special By Tracy Special by Tracy
Tux: Mickey’s Tuxedos

Hidden right here in Coltons Point 🌹This stunning private rose garden feels like something straight out of a storybook. ...
05/20/2026

Hidden right here in Coltons Point 🌹

This stunning private rose garden feels like something straight out of a storybook. Every path, bloom, and little tucked-away corner was absolutely dreamy to photograph.

The best part? The owner, , offers property access for photography sessions, and she’s also hosting an Open Garden this Saturday from 2–4 PM for anyone wanting to come explore the blooms in person!

If you’ve been wanting romantic portraits, family photos, senior sessions, or even just updated photos surrounded by flowers at peak bloom season, this location is incredible.

Highly recommend checking it out while everything is in bloom!

Clients pm for details!
Photographers schedule times by emailing
[email protected]

Address

29500 All Faith Church Road
Mechanicsville, MD
20659

Website

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