Proposal · Prospect Hill Tower, Somerville

Prospect Hill Proposal, Somerville — James & Jacqueline

“The best skyline view in the city, and almost nobody on it.”

Location: Prospect Hill Tower, Somerville
When: Friday, 6:00 PM · late August (sunset 7:25)
Type: Surprise proposal + portraits
Referred by: JJ & Payton
Guide: Prospect Hill Tower proposal guide

James found me the best way anyone can — JJ and Payton, whose proposal I'd shot in the Public Garden, told him to call me. He already had Prospect Hill Tower in mind, which tells you he'd done his homework. You get the full Boston skyline from up there and a fraction of the people you'd fight through anywhere downtown, and for a surprise that quiet matters more than pretty does.

The plan

He'd originally picked a Sunday, then moved it to a Friday evening at six, which turned out to be the better call: late August sunset was around 7:25, so we had a long, soft window with the whole hill to ourselves. James handled the cover story on his own — dinner nearby at 7:30, so a walk beforehand was nothing out of the ordinary — and then went a step further and scouted the exact spot himself, sending me photos a day out so I knew precisely where he'd stop.

The moment

On the night, they came up the Munroe Street stairs and I was already in position above them, following at a distance. There was no timing for him to hit and no mark to find; my rule is always that the person proposing should only have to think about one thing. Jacqueline never picked me out of the hill, and when James stopped walking, I was already shooting.

Portraits after

Afterward we stayed up there for portraits with the skyline behind them while the light dropped, which is exactly why I push the portrait package — you're already up there, you're both still buzzing, and that hour is the loosest either of you will ever be in front of a camera.

If Prospect Hill is on your list

Come up the Munroe Street stairs.
Go before sunset rather than at it — on this night, 6:00 for a 7:25 sunset gave us the whole window.
A weekday evening beats a weekend afternoon; the hill was empty.
The rest — where to stand for the skyline, parking, the T, dinner nearby — is in the Prospect Hill Tower proposal guide. Proposal photography starts at $699.