How to make the most of your engagement session

rebeccacastonguay
May 31
4 min read

If you're recently engaged (yay! 🥂), chances are you're knee-deep in wedding planning and wondering how to make your engagement session really count. As a New England wedding photographer with over a decade of experience capturing love stories from the rolling hills of the Berkshires to the breezy shores of Cape Cod, Connecticut and Newport, I’m here to help you turn that hour or two in front of the camera into a memory-making, confidence-building experience that sets the tone for your entire wedding journey.

One of my recent favorites? Nick and Vanessa’s engagement session at The Starting Gate at GreatHorse in Hampden, Massachusetts. Their session was the perfect mix of romantic, elegant, and totally them—complete with that dreamy golden hour light, sweeping views of the golf course, and of course, plenty of laughs. (We had so much fun!) If you’re planning a wedding at The Starting Gate, you already know how special it is—this session only confirmed how perfect it is for timeless, editorial-style engagement portraits that feel fresh and full of personality.

Whether you’re getting married in the Berkshires of Western Massachusetts, on the shoreline of Connecticut beaches or on Cape Cod, or having a luxe coastal celebration in Newport, here are my top tips to help you make the most of your engagement session:

1. Location, Location, Location (and Let’s Get Personal!)

Choose a location that feels like you as a couple. Love the mountains and countryside? Let's head to the Berkshires. Obsessed with ocean views? Cape Cod or Newport is calling. Want something classic and elegant with top-notch scenery? The Starting Gate at GreatHorse is one of my favorite places to photograph—you truly can't beat the way the sun sets over the hills there.

Nick and Vanessa chose The Starting Gate because it's where Nick proposed to her—it was a great idea to bring the engagement session full circle. Despite the fact that their wedding won't be held there, they share so many fond memories and therefore it was comforting to be in a space they could call home.

2. Outfits Matter—but Comfort Is Key

Pick outfits that reflect your unique style and make you feel confident and comfortable. Think flowy dresses, structured neutrals, or well-fitted casual pieces that photograph beautifully in natural light. For two looks, I suggest one dressier option and one more laid-back, cozy style—especially if we’re venturing through beach grass or walking the trails at a Berkshires estate.

Pro tip: Stay away from heavy patterns and neon colors. Soft, neutral tones with texture (linen, knits, soft cottons) are your best friend!

3. Treat It Like a Date Night

This is your time to connect - I'm simply there to capture it. Bring a blanket and a bottle of bubbly, go barefoot in the sand, kiss a little longer. Don’t stress about being perfect—I’m here to guide you the whole way, so the pressure is off. The most meaningful photos happen when you’re just being yourselves.

One of my favorite moments with Nick and Vanessa? They took a second to practice their dip kiss at the gazebo with no music at all. It was so them—sweet, a little silly, and totally in the moment. That’s the kind of magic we’re going for.

4. Golden Hour Is Gold for a Reason

That soft, glowy light you see in my photos? That’s golden hour. About 60–90 minutes before sunset, the light is at its most flattering and dreamy. We’ll try to plan your session around this timeframe to make sure you look your absolute best (think sun-drenched skin, glowing smiles, and backgrounds that pop). No sun? No problem. Try to go with the flow, often overcast lighting creates moody imagery but it's also helpful to avoid harsh shadows. We can work with what mother nature provides us and if there's a few raindrops - don't panic. Those can be just as lovely!!

5. Let’s Talk Vibes: What to Expect When You Work with Me

My approach is warm, friendly, and full of laughs. I want you to show up as YOU. My style is a combination of bright and airy timeless photography with an artistic and editorial edge. Elevating the moment ever so slightly as if it could be featured in a magazine. I’ll confidently give you just enough direction to feel comfortable—but not stiff or overly posed. I want you to look back at your engagement photos and feel the experience again together, not like you were trying to be someone you saw on Pinterest. (Don't get me wrong - I love inspiration, but I want it to be authentically you).

Your engagement session is also our chance to build trust and chemistry before the wedding day. By the time your celebration rolls around, you’ll feel like you’re being photographed by a friend—and one who is on a mission to find the most flattering light and capture moments that will last a lifetime.

Ready to Plan Your Session?

If you're recently engaged and looking for a New England wedding photographer who will bring out the real you, laugh alongside you, and deliver photos you’ll want to frame forever, I’d love to hear from you. Let’s plan your engagement session in the Berkshires, Cape Cod, Newport—or right here in Western Massachusetts!

Reach out to me here ➝ www.rebeccacastonguayphotography.com/contact or come follow me on Instagram @rebeccacastonguayphotography for more love stories and behind-the-scenes moments.