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The coziest little spot on the Internet for inspiration, advice, and ideas for weddings in Boston and across New England.
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Most couples ask the same question early on: why do engagement photos matter if the wedding is what really counts?
The hesitation usually isn’t about the photos themselves, it’s about how it will feel to be in front of the camera. That’s where engagement photos become less about the images and more about the experience. They create space for you to feel comfortable, connected, and at ease long before your wedding day arrives.
An engagement session isn’t a test run for looking perfect. It’s a chance to slow down and experience what it feels like to be photographed in a way that’s relaxed and natural.
From the first moment we connect, my priority is helping you feel comfortable being yourselves. I’ll guide you when needed, but the focus is always on real interaction, talking, moving, and sharing quiet moments together. When you feel good, your photos reflect that without effort.



Feeling comfortable in front of the camera changes everything.
Couples who do engagement photos often notice:
That comfort allows me to capture the moments that matter, big and small, without interrupting them. Your wedding day moves quickly. Having one less thing to think about makes a real difference.
I include engagement photos with every collection because building trust and connection matters to me.
Your wedding day isn’t the time for us to meet for the first time. An engagement session gives us the opportunity to get to know each other in a relaxed, low-pressure setting. You get a feel for how I work, and I get to learn how you interact together, what feels natural, what brings out genuine moments, and when to step back.
That connection allows your wedding day to feel easier. You don’t have to wonder what to do or how it’s supposed to feel. You can simply be present, knowing you’re supported by someone who understands you as a couple.



By the time your wedding day arrives, the camera feels familiar.
You already know:
That confidence allows your day to unfold naturally and your photos to reflect it honestly.
Not at all.
Engagement photos work best when they feel like you. That might mean a place that feels familiar, a quiet walk, or time together without expectations. If you’re looking for ideas or want to understand how flexible engagement sessions can be, The Knot offers a helpful engagement photo planning guide that walks through different approaches in a practical, low-pressure way.
The goal isn’t perfection, it’s connection.



If you’re unsure whether engagement photos are worth it, ask yourself this:
Do we want our wedding photos to feel relaxed, authentic, and true to us?
If the answer is yes, engagement photos are often the first step in making that possible.

If you’re planning a New England wedding and want your photos to feel relaxed, authentic, and true to you, you can learn more about my approach and view full galleries at daniellelittlesphoto.com. It’s the best place to get a feel for how I work and whether it feels like the right fit for you as a couple

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When couples start searching for questions to ask a wedding photographer before booking, it’s usually because they want to feel confident, not just about how their photos will look, but about who they’re trusting with one of the most important days of their lives.
Your photographer is one of the vendors you’ll spend the most time with. From getting ready, to portraits, to navigating family dynamics and timeline shifts, they’re right there with you. Your wedding day should feel just as effortless as saying yes to your person and asking the right questions upfront helps make sure you don’t regret your decision later.
Below are the most important questions to ask a wedding photographer before you book, and why each one truly matters.
This question goes beyond aesthetics, it’s about how your photographer shows up.
Some photographers are very directive, while others focus on documenting moments naturally as they unfold. What matters most is choosing someone whose approach aligns with how you want your day to feel.
Your wedding day shouldn’t feel stiff or overly posed. It should feel relaxed, natural, and fun.



Instagram shows the best moments, but full galleries tell the full story.
Looking through an entire wedding helps you see:
This gives you a much clearer picture of what to expect.
Every wedding is different, from venues and timelines to lighting and logistics.
Asking this helps you understand whether your photographer has experience navigating situations similar to yours, whether that’s:
Experience brings calm energy, and that makes a huge difference on a wedding day.



This is an important one that often gets overlooked.
Some photography teams use associate photographers, while others guarantee the person you meet is the one who shows up. There’s no wrong answer, as long as it’s clear.
You deserve to know exactly who will be there documenting your story.
A second photographer can provide additional coverage, more angles, and peace of mind during busy moments.
Ask whether:
This helps you decide what level of coverage makes the most sense for your day.



Most couples don’t consider themselves “photo people,” and that’s completely normal.
Your photographer should know how to:
Comfort leads to photos that feel genuine and true to you.
This question shows whether your photographer is invested in your experience, not just the photos.
A great photographer will help you:
Your wedding is supposed to be enjoyable, not stressful.



Photographers often have one of the best understandings of how a wedding day flows.
Ask if they:
Thoughtful planning makes the entire day feel smoother.



Life happens, and this question gives peace of mind.
A professional photographer should have:
You should never feel uncertain about coverage on your wedding day.



While it may not be the most exciting question, it’s an important one.
Insurance protects you, your guests, and the venue — and many venues require it. It’s also a strong indicator of professionalism.
Turnaround times vary, so it’s important to ask upfront.
Clarify:
Clear expectations make the waiting process much easier.
Your wedding photos are once-in-a-lifetime memories.
Ask about:
Your photos should be cared for long after the wedding day ends.
Your wedding photographer does so much more than take photos.
They’re there to help you plan, fix your hair, sew a button back onto your dress, wrangle family members for portraits, or grab you a glass of water when you need one. You should feel like a priority, supported, and completely at ease.
If you’re looking for a photographer who brings calm energy, creative storytelling, and undivided attention to your wedding day, I’d love to connect and learn more about your story.

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What questions to ask at a wedding venue. Picking a venue is probably one of the hardest parts of wedding planning. It sets the tone, the vibe, and often determines a lot of your wedding-day logistics. Are you dreaming of something romantic and classic? Rustic and laid-back? Chic and modern? Once you’ve figured out the vibe, you’ll still need to tackle the details.
What’s your budget? What’s included? What’s the rain plan? There are so many important questions to ask when you’re venue shopping, and I’m here to help you go in prepared.
Here are ten key questions to ask while touring wedding venues:
This one seems simple, but it varies a lot from place to place. Ask about:
This is so important—especially if you’re doing a first look or want to get ready on-site. Many venues only allow access 1–2 hours before the ceremony, which can make timing tricky for hair, makeup, and getting dressed.
Also ask:
Outdoor ceremonies are beautiful, but we know New England weather doesn’t always cooperate. Make sure you:
I’ve photographed indoor ceremonies in beautiful spaces—but also in cramped rooms that clearly weren’t intended for that purpose. You deserve a beautiful Plan B.
It’s common for venues to include a “coordinator,” but what they do can vary widely. Some are very hands-on, while others simply unlock the doors. Be sure to ask:
Knowing exactly how involved your venue coordinator is will help you determine if you also need to hire a separate wedding planner or day-of coordinator.
No one wants to think about postponing or canceling their wedding—but it’s important to know the venue’s policies just in case. Ask:
Having clear answers upfront gives you peace of mind and helps you feel more secure about your investment.
Some venues require you to meet a certain dollar amount in catering or bar service to book the space. This can greatly impact your overall budget. Be sure to ask:
Knowing this helps you plan your guest list and catering choices accordingly.
Vendor flexibility is huge—especially if you have a favorite caterer or want to bring in specific rentals or dessert options. Some venues only allow vendors from a preferred list, so ask:
Understanding vendor policies early will help you avoid disappointment down the line and ensure your wedding reflects your vision.
Every venue has rules to keep things safe and beautiful, but it’s important to know what’s allowed and what’s not. Ask about:
Knowing the restrictions upfront helps you plan your celebration without surprises.
Photos are a huge part of your wedding day memories, so ask about access:
This way you can plan your photo timeline and make the most of the venue’s best backdrops!
Knowing the venue’s capacity ensures your guest list fits comfortably and meets any fire code requirements. Also, ask:
Getting this info early helps with planning invitations, catering, and seating arrangements smoothly.
This list could honestly go on and on, but I don’t want to overwhelm you! I believe these 10 questions are some of the most important to ask when touring wedding venues. Once you’ve found the perfect venue and locked it in, you might be starting to research other vendors—including your wedding photographer. If that’s the case, you can check out my blog on what to ask your wedding photographer here to keep your planning on track!
Planning your wedding is exciting and I’d love to help capture your special day! If you have any questions about wedding photography or want to check my availability, don’t hesitate to contact me here.

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If you’re looking for a quiet, scenic, and romantic location for your Wingaersheek Beach engagement photos, this spot checks every box.
When Camryn and Zach first reached out to schedule their engagement photos, they weren’t quite sure where they wanted to shoot but they did know they wanted the beach. Since we were planning their session during the off-season, I immediately suggested Wingaersheek Beach in Gloucester, MA. It’s one of the most beautiful beaches in Massachusetts and honestly, all of New England.
We pretty much had the beach to ourselves, which is one of the perks of planning engagement photos during the off-season. The forecast had called for fog, rain, and chilly temps but Camryn and Zach were totally down for it. And I’m so glad they were! If being a wedding photographer in New England has taught me anything, it’s to go with the weather because magic can happen even when the forecast says otherwise.
We ran around the beach (literally), climbed the rocks, and captured the most beautiful, candid moments including a few sweet photos with their adorable 4-month-old daughter. She is just the cutest and totally stole the show for a few frames.
Wingaersheek Beach engagement photos always offer something different, whether it’s a golden sunset or a misty shoreline. The soft colors, wide skies, and unique rock formations make it a dream location for couples who want natural and timeless photos.






















Getting to know Camryn and Zach through this session made me even more excited to photograph their wedding day. These two are so much fun to be around, and their love for each other (and their little one!) made this session so special. I’m already counting down the days to August!
Thinking about your own engagement photos? Whether you’re dreaming of a beach session, something in the mountains, or a cozy city vibe, I’d love to help you plan it. My approach is relaxed, fun, and all about capturing who you are together.
Let’s connect! Contact me here to start planning your engagement session or wedding photography.

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My 2025 wedding season kicked off with Emily and Nate’s celebration at The Venues at the Factory, and it could not have been a more perfect way to begin the year. This unique space, with its mix of industrial charm and modern touches, was the ideal backdrop for a day filled with so much joy, love, and unforgettable moments. Emily and Nate have such an easy & fun relationship. There were so many laughs throughout the day.
One of the best parts about getting married at The Venues at The Factory is the convenience, everything is right there, including beautifully designed Airbnbs located in the same building. Emily and Nate took full advantage of this setup to keep their day stress-free and seamless. With no need to worry about travel or timing, they got ready just steps away from their ceremony space. These thoughtfully decorated getting-ready suites were the perfect backdrop for flat-lays, final touches, and quiet moments before the celebration began.












Emily and Nate chose to skip the first look, saving that special moment for when they saw each other at the ceremony for the first time and it was absolutely worth the wait. To make the most of the timeline, we captured individual wedding party and family portraits ahead of time. In true New England April fashion, it poured all day, but The Venues at the Factory offers plenty of beautiful indoor space for photos. We made full use of the industrial-chic interiors for portraits that were both stylish and stress-free.






To say it was emotional would be an understatement. Emily and Nate were both so ready and excited to see each other, it’s always such a special moment to capture that first look at the altar. With heartfelt vows that even included their shared love of Disney, there wasn’t a dry eye in the room. Surrounded by family and friends, they tied the knot and officially became husband and wife in a ceremony full of love, laughter, and meaningful memories.











Since Emily and Nate didn’t do a first look, all the portraits along with the remaining family and wedding party photos happened right after the ceremony. And while the rain kept us indoors, The Venues at the Factory has no shortage of amazing spots to work with. We took full advantage of the industrial textures and moody lighting to create portraits that felt stylish, relaxed, and true to the day. Later during the reception, we snuck away for a few more portraits just the two of them, to soak it all in and capture some quiet newlywed magic.











Emily and Nate were so ready to party and their reception did not disappoint. Fusion Function absolutely crushed it, keeping the energy high all night long with an epic mix of hits (including plenty of Bad Bunny, of course). The dance floor was packed, their friends surprised everyone by showing up in hilarious blow-up suits, and the entire night was just non-stop fun. It was the kind of reception where you could feel the joy in the room and no one wanted it to end.


















One of my favorite parts of Emily and Nate’s day were the subtle but sweet Disney nods woven throughout. From “Happily Ever After” signs to a whole new world moment during the father-daughter dance, every detail felt personal and meaningful. Their vows even included Disney references that had everyone smiling, and instead of a traditional guest book, guests signed a Spaceship Earth-themed sign a perfect tribute to their shared love for the magic.
Emily and Nate’s wedding at The Venues at the Factory was the perfect mix of fun, emotion, and personal touches, such an incredible way to kick off my 2025 season. If you’re planning your own wedding and want photos that feel authentic, joyful, and totally you, I’d love to chat.
The Vendors:
Photographer – @daniellelittlesphoto
Venue – @thevenuesatthefactory
DJ – @fusionfunctionent
Officiant – @marriedbylb
Dessert – @queencitycupcakesnh
Caterer – @kc_ribshack
Hair & make-up – @angeltouchbeauty_team
Dress – @chantillyplace
Suit – @generationtux
Invitations – @truly.engaging
2nd photographer – @chelsearushphotography

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Arianne and George had the most beautiful day at Waverly Oaks. With the perfect mix of gorgeous fall weather, a stunning location, and the love of their closest friends and family, everything came together effortlessly. Waverly Oaks Golf Club provided the ideal backdrop for a celebration that felt relaxed, joyful, and full of heart.
I first met Arianne and George the winter before their wedding for their engagement session. They chose a new location for me in Boston, one that was extra special because it’s where they got engaged. From the moment I met them, it was clear how much love and respect they have for each other. It all felt so natural and effortless. I remember one moment in particular: I asked them to pretend I wasn’t there and just enjoy being together. Without hesitation, George started twirling Arianne and dancing with her, something they love to do at home. It was pure joy and so authentically them.
Fast forward to their wedding day in October. We started the morning at a nearby hotel for getting ready photos. Everything was so smooth and organized, thanks in large part to Arianne, who is incredibly on top of things, and her amazing bridal party and mom, who were beyond helpful. They had everything laid out and even reserved a separate room free of hair and makeup products so we had a clean, clutter-free space for photos.
I can’t stress this enough. Assigning tasks to your bridal party really makes the day easier. Because they were so prepared, I was able to start with flat-lay photos in that clean space. Not only did they have gorgeous details ready for me to photograph, but their florist (thank you @texturefloraldesign) also provided the most stunning floral accents. It made such a difference and truly elevated the entire gallery.

























Arianne and George chose to do a first look and share private vows before their ceremony, and honestly, it’s one of my favorite parts of the day. Even with two photographers and two videographers present, it still felt incredibly intimate. They were completely focused on each other and those quiet, emotional moments before becoming husband and wife.
After their first look, we moved right into portraits. While we did more photos later in the day, this gave us a beautiful variety and helped the timeline stay relaxed. We also took advantage of this time to do wedding party and family photos. One of the best parts of doing a first look is that you get to spend more time with your soon-to-be spouse, shake off some of those pre-ceremony nerves, and get all the formal photos done early. That way, after the ceremony, your wedding party and family can head straight to cocktail hour, and you can take a few more photos and get a minute to breathe!













The ceremony was held outside at Waverly Oaks, just as the sun began to set, and the lighting was absolutely beautiful. There was a soft golden glow over everything, creating the most romantic atmosphere. Arianne looked radiant as she walked down the aisle, and even though she and George had already seen each other during their first look, the emotion on their faces made it feel like they were seeing each other for the first time all over again.
Their ceremony was filled with so much love and joy, and they ended it with the best dip kiss I’ve ever seen. It was such a fun, cinematic moment that perfectly captured their energy as a couple. Everyone was cheering, and you could just feel how happy and present they were in that moment.










After the ceremony, we took full advantage of the setting sun to capture those dreamy golden hour portraits. We hopped on a golf cart and explored a few beautiful spots around the property before heading back up to the venue to finish the rest. The sunset did not disappoint, it gave us the softest, most magical light, and Arianne and George looked absolutely stunning. It was such a peaceful, fun moment for them to soak everything in before heading into the excitement of the reception.






By the time the reception began, everyone was ready to celebrate. The evening kicked off with a beautiful first dance, followed by two sweet dances with their moms that had everyone smiling. One of the most touching moments was a surprise anniversary dance dedicated to Arianne’s aunt and uncle—who now share a wedding anniversary with them. It was such a thoughtful gesture and had the whole room cheering.
From there, the dance floor stayed full all night. The kids especially brought the energy, showing off their best moves and keeping the party going strong. It was the perfect end to a day filled with love, laughter, and unforgettable moments.


















Arianne and George’s wedding at Waverly Oaks was such a beautiful reminder of why I love what I do. From emotional vows and golden hour portraits to thoughtful details and nonstop dancing, their day was filled with so much joy and intention. It was truly an honor to be a part of it.
Vendor Team:
Photographer – @daniellelittlesphoto
Venue – @waverlyoaksgc
Dress – @chryssiesbridal
Suits – @menswarehouse
DJ – @benwayentertainment
Florist – @texturefloraldesign
Make-up & hair – @dropdeadgorgeousri
Videographer – @ez.videoproductions
Desserts – @montiliosweddings
Invitations – @minted
2nd shooter – @photosbyarlinda
If you’re planning your own wedding and are looking for someone to document it with care, attention to detail, and a personal connection, I’d love to chat. You can get in touch through my contact page or send me a message on Instagram @daniellelittlesphoto. Let’s create something beautiful together.
Keywords: MA weddings, wedding photographer, MA wedding photographer, NH weddings, Waverly Oaks Wedding, wedding portraits, Waverly oaks golf club
