Annapolis and Eastern Shore Wedding Photographer

Annapolis

Wedding Photographer

Celebrations on the Bay Wedding Photography by Annapolis Wedding Photographer Jenna Leigh Photography
Annapolis Wedding Photos
Eastern Shore Wedding Photography
Chesapeake Bay Beach Club Exterior Wedding Picture
Herrington on the Bay Wedding Photography

I'm Jenna Leigh — and the Chesapeake Bay region is some of the most rewarding work I do. In more than 16 years of wedding photography, I've worked across the greater Annapolis area and Eastern Shore — from waterfront estates on the western shore to historic manor houses in Chestertown to the sweeping bay views of Stevensville.

That geographic depth shows up in ways couples don't always expect: I already know how Herrington on the Bay's eastern light shifts across the ceremony lawn at golden hour, and how the Chesapeake Bay Beach Club's waterfront terrace reads on camera in every season.

My style is vibrant and true-to-life — clean, bright images that look exactly like your wedding day felt, not filtered or faded into a trend that won't age well.

Featured in Washingtonian Magazine ·

Knot Best of Weddings Hall of Fame

16+ Years · 350+ Weddings

The bay light, the water, the moments between moments.

My job is to make sure none of it gets away from you.


Vibrant, true-to-life wedding photography for couples who chose one of the most beautiful stretches of Maryland coast — and want images that show it.

Annapolis Weddings

Chestertown, Maryland

Brittland Estates Wedding

Tracy's Landing, Maryland

Herrington on the Bay Wedding

Stevensville, Maryland

Chesapeake Bay Beach Club Wedding

"Jenna captured our day beautifully, every photo feels natural, heartfelt, and full of joy."


Stefanie & Warren

Herrington on the Bay Wedding Photography Couple by Jenna Leigh Photography
Solid pale pink background in soft muted tone.

Beyond the bay

Venue Pricing Guide

From waterfront estates on the western shore to historic manor houses on the Eastern Shore, I've put together a comprehensive pricing guide covering 20+ Annapolis and Eastern Shore wedding venues — ceremony fees, catering minimums, and what couples actually spend in 2026.

FAQ

Q: You're based in New Market — how familiar are you with Annapolis and Eastern Shore venues?

A: Very. I've photographed weddings across the region — from the Chesapeake Bay waterfront in Tracy's Landing and Stevensville to historic manor estates in Chestertown. I know how the bay light behaves at these venues and what makes each one distinct to photograph.

Q: Do you have experience at my specific Annapolis or Eastern Shore venue?

A: Likely yes. I've photographed at Herrington on the Bay, Chesapeake Bay Beach Club, Brittland Estates, and other venues across the region. Even if I haven't shot your specific venue, I research every location thoroughly before the wedding day.

Q: How far in advance do Annapolis and Eastern Shore couples typically book?

A: Most couples book 12–18 months out. Peak waterfront dates — particularly late spring and fall — fill early. If you have a specific venue or date in mind, it's worth reaching out as soon as your venue is confirmed.

Q: What does "vibrant and true-to-life" mean for waterfront and bay venues specifically?

A: The Chesapeake Bay region has extraordinary natural light — the water reflections, the open sky, the golden hour over the bay. My style captures that light accurately and fully rather than fading or muting it. Your venue looks like your venue, with all the color and atmosphere that made you choose it.

Q: Do you work with a second shooter?

A: Yes. For most Annapolis and Eastern Shore weddings I bring a second photographer, which means simultaneous coverage across getting-ready locations, complete ceremony coverage from multiple angles, and more comprehensive cocktail hour documentation — especially valuable at waterfront venues where guests spread across docks, lawns, and interior spaces.

Q: What happens after we book?

A: You'll receive a detailed questionnaire covering your venues, timeline, family dynamics, and portrait priorities. We'll schedule a planning call, build your shot list together, and I'll scout any portrait locations I haven't covered recently. On your wedding day, you won't need to think about any of it.

Annapolis and Eastern Shore Wedding Photography

Annapolis Wedding Photography


Let's Tell your story


I'd love to hear about your Annapolis venue, your vision, and whether we're the right fit.

Based in New Market, Maryland · Photographing weddings throughout Washington DC · Northern Virginia · Maryland · Annapolis · Loudoun County · and the broader DMV