Plan your Hudson Valley proposal

Engaged couple laugh and cry after proposal in front of golden trees at Storm King Art Center in New Windsor, NY in the Hudson Valley.
Newly engaged couple laugh and walk down path lined with golden trees at Storm King Art Center in New Windsor, NY in the Hudson Valley.

So you're going to make it official! Congratulations!


You probably have a ton of questions. You're in the right place! Just scroll down for a useful guide to planning the big moment.


As you read through the guide below, keep in mind that each proposal is unique. These hints, tips, and suggestions are geared around intimate proposals in the Hudson Valley, but can be customized to your own history, needs, values, and location. I would love the chance to discuss details, click the button below if you have questions you'd like to jump right in with!

Tips for the perfect proposal session

1. How do I stand when I propose?

Newly engaged couple laugh and embrace on hilltop in front of golden trees at Storm King Art Center in New Windsor, NY in the Hudson Valley.
  • If possible, scout out your location ahead of time. I often do this too, and can look for where I think the best photos will be


  • Text your photographer when getting close to the location. A simple "P" for parked or "W" for walking does the trick!


  • When you arrive to your location, look for shade if possible


  • If you can, position yourselves so your profile is facing the photographer (so you can see them out of the corner of your eyes)


  • Once in your spot, don't worry about the photographer. They can move for the best angle, it's best if you stay where you are

2. What do I wear when I propose?

Couple matching black outfits sitting with light coming through the windows at Bird Bottle Inn at Garrison, New York
  • If possible, frame the proposal as a "get away" so that nails are done and hair is fixed!


  • Clothes colors that match are best, especially if they are not so bright they stick out.


  • Comfortable shoes if you're walking around


**Bright color clothes can reflect light and cast colors across faces**

3. Questions to ask your photographer

A newly engaged couple against scenic tree foliage in the background at Boscobel House & Gardens in Garrison, New York

When booking a photographer, here are some important questions to keep in mind (beyond starting price):


  • Does the photographer provide coverage for just the proposal? Or do they stick around and take more photos afterwards?


  • Do they have experience with proposals or weddings? It's important to have an experienced person on your side who is adaptable to changing light or weather conditions.


  • Will they arrive early and scope out the place/send you updates?


  • Will they help you build a plan for your perfect proposal, or are they just going to show up and take pictures?


  • Are they insured?


  • Do they have package enhancements?


  • What's their turn-around time for photos? Proposals are unique and you probably want those photos soon...I'll get you some before you go back to work Monday :)
Newly engaged couple laugh and embrace on hilltop in front of autumn trees and mountain views at Storm King Art Center in the Hudson Valley.

Storm King Art Center Proposals


The Art Center should be on every Hudson Valley list! Beautiful scenery and fantastic art set the perfect stage for your proposal and engagement photos. Take the Metro North to Beacon from New York City and then the shuttle from Beacon for $10! They do require a site fee (which I can help you navigate) and photographer's insurance (which I have), but it is absolutely worth it. Storm King is gorgeous in any season!

Top Cold Spring proposal locations

Best spots in and around this iconic Hudson Valley village

Boscobel House and Gardens

Amazing and historic riverside mansion with beautiful gardens. Typically requires a site fee, but the fee is covered if you book photography with me!

The Bird and Bottle Inn

Romantic and vintage with a modern craft twist, this is the spot if you'd like to stay either before or after the proposal.

Little Stony Point

The best spot for those who want to hike and get to gorgeous views, with minimal effort!

Downtown Cold Spring

For those of you who want the cute, quaint, and art-inspiring vibe of downtown Cold Spring.

West Point Foundry Preserve

Short trails, awesome views, quick access to town are pros of this out-of the way location. You may be the only people here!

Cornish Estate Trial

If you feel at home in the woods, if being in the shade of the trees on a well-worn but little trafficked trail rejuvenates and recharges you, this is your spot!

Where to eat and stay in the Cold Spring area


Suggestions for that engagement celebration!

The Bird and Bottle Inn


Situated just outside of Cold Spring in Garrison, this place has an AWESOME farm to table seasonal menu, a wonderful atmosphere, creative cocktails. It is also a great place to stay!

Hudson House Inn


Right on the Cold Spring waterfront, with a charm and atmosphere that's only surpassed by the steak and fish entrees. Book a stay here to be right on the iconic Main Street.

The Pig Hill Inn


A popular location for romantic getaways. This historic inn, right on Main Street before crossing the train tracks, is a beautiful anchor point in town.

Front of the Cozy Corner Cafe with flowers in window box and rustic lighting through window in Cold Spring, NY in the Hudson Valley.

Brunch spots


The Cozy Corner Cafe and The Foundry Rose Cafe are cute little spots with amazing brunch. Try both!

Start your plan by first deciding...

FAQ for the person planning a proposal

Where you want to propose?

Do you two have a special location? Something from your shared past that is meaningful?

What time of day are you considering?

Photographically, light is best either an hour before sunset or an hour after sunrise.
If you have dinner plans though, you may want to propose earlier.

Is it going to be a surprise?

Your photographer will help you plan accordingly!

Are there activities involved in the proposal?

Are you popping champagne? Picnicking? Hiking?
Involving pets or other people?
Super helpful to know!

How much do you need covered?

A. Just the proposal moments and immediate reactions
B. The proposal, reactions, and more pictures afterwards (like an engagement session)

 

Plan your proposal

 

Couple showing engagement ring to family during autumn while holding a bouquet of red roses at Storm King Art Center in the Hudson Valley.
*
*
*

I would love to hear about your story: your partner's name, your date, your dream vision for your proposal, anything else!

Some of my favorite proposal albums

Steve and Lindsay

The Bird & Bottle Inn

Full Album

Ari and Ezra

Storm King Art Center

Full Album

Jade and Griffin

Boscobel House

Full Album

What sets me apart

Newly engaged couple hug and look at ring in a garden with yellow flowers at West Point Foundry Preserve in Cold Spring, NY in Hudson Valley

Authentic, timeless, and natural couple sessions photography


With me as your photographer you have an empathetic, calm, patient, and creative professional documenting your most important moments and memories. My job is to document and facilitate your unique proposal...your job is to enjoy it!

Kind words from clients


"Highly recommend hiring Matt for engagement/wedding photos! Matt went to the proposal location ahead of time to scope it out, take photos, and determine the best precise spot based on background and lighting. He truly went above and beyond. He has a background in nature photography and the natural beauty of the hudson valley is really pronounced in our photos, something we wanted. I think he went over the allotted time because he saw a brook last minute that made for some great photos. He was a consummate professional from the jump."


Daniela and Chris (Engaged in Cold Spring 2024)

Let's connect!

*
*
*

I would love to hear about your day: your partner's name, your date and venue, your dream vision, anything else!

Matthew Rigby smiling with cameras on leather straps at an outdoor Hudson Valley wedding with stone wall, trees, and hills in background.

I am a wedding photographer based in Garrison, NY, and serve couples throughout the Hudson Valley. Whether you’re planning an intimate day at The Garrison, a barn wedding at Fortune Valley Manor or the Barn at Villa Venezia, a brewery or winery celebration in Warwick or Chester, or a creative elopement in Beacon or Cold Spring, I’m here to help you feel relaxed and seen while documenting the beauty of your day with a thoughtful, artistic eye.



hello@matthewrigbyphotography.com

860-218-8494