Eight years together, a place with personal meaning, and a forecast that kept us checking the weather! Jay’s surprise Mount Sugarloaf proposal in South Deerfield, MA took a little flexibility to pull off, but everything worked out perfectly!

Jay contacted me a few weeks before he planned to propose to his girlfriend. He already knew where he wanted it to happen. Mount Sugarloaf holds special meaning for the two of them, making it the perfect place to ask her to marry him.

We had the location and a plan. Now we just needed the weather to cooperate!

From Meeting in High School to Making a Home in Deerfield

Jay and his girlfriend are both from the South Shore and met in high school. Eight years into their relationship, their story had brought them to Deerfield, where they moved into their first apartment together.

I love when couples choose a proposal location because of their connection to it. A beautiful setting is a bonus, but knowing a place already means something to you makes the moment even more personal.

For these two, Mount Sugarloaf was already part of their story. Jay’s proposal gave them another reason to remember it.

Planning a Surprise Proposal Around a Nor’easter

In the week leading up to the proposal, Jay and I were hoping for good weather. Of course, New England had other ideas. A nor’easter was headed our way for the weekend!

We had a backup plan, but we kept watching the forecast to see whether we could still make Mount Sugarloaf work. Ultimately, we decided to move the proposal to Saturday morning, when the chance of rain looked lower.

There was still some uncertainty, but we decided to give it a shot. And I’m so glad we did! It didn’t rain at all the entire time we were there! Score!!

Overcast Skies Made for Beautiful Proposal Photos

The morning was very overcast, which ended up giving us the most even light for their photos.

If you know me, you know I love sunshine. But cloudy skies have their advantages, too! The cloud cover softened the light, without the strong contrast between bright sun and deep shadows.

For Jay’s Mount Sugarloaf proposal, that meant beautiful light and no rain. After all that forecast watching, we couldn’t have asked for a better outcome!

Eight years into their relationship, Jay asked his girlfriend to marry him in a place that already mattered to them both. I’m so happy I got to photograph this milestone!

Planning Your Own Surprise Proposal?

A few things from Jay’s experience are worth keeping in mind when planning an outdoor proposal:

Choose a location with meaning. Think about places that are part of your relationship: somewhere you spend time together, a favorite view, or a spot tied to a shared memory.

Contact your photographer before the day. Jay reached out a few weeks ahead, giving us time to talk through his plans and make adjustments as the date approached.

Have a weather backup and allow some flexibility. Moving to Saturday morning made all the difference for this proposal. You can’t control the forecast, but having another option gives you room to adapt.

Thinking about a Mount Sugarloaf proposal or planning to pop the question somewhere else? I’d love to hear your ideas and help photograph the surprise!

Contact Alison Marie Photography to start planning your proposal!