Most Photographed Street in Boston: Acorn Street Engagement Session

The Most Photographed Street in Boston: An Acorn Street Engagement Session

Posted in: Elopements & Travel Weddings, Locations, Real Weddings

Ah Acorn St… the most photographed street in Boston. I swear there was a month where I was around that neighborhood almost every weekend. The bricks are so iconic and gorgeous — the reds in fall are stunning. A Beacon Hill engagement session is something special.

beacon hill engagement session

Beacon Hill Engagement Sessions: Stumbling around the neighborhood

The best way to do a Beacon Hill engagement session is literally just to stumble around the neighborhood. Chat about random things, bump into each other and just enjoy the time and space together.

acorn st engagement session

Stop at some of the ice cream shops or coffee places, grab champagne at one of the bars. It’s way more fun to have an engagement session where you DO activities together versus just pose in front of stuff together. If you need more help with how to do a couples session click here.

boston engagement session

Although this session was very early in my career, I remember how one of the guys forgot his ring so we solely focused on his partner’s ring, this one. One of the two is a model while the other was so nervous. It was fun to see Jon bring Tyson in and make him feel at ease — as any solid partner does. The way that they melted into one another was goal-setting and something I remember seeing to this day.

boston wedding photographer

Since those days, Acorn Street now has a permitting system for photoshoots. It’s a coveted location for engagement sessions and is supposedly the most photographed street in Boston.

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The best part about walking around the neighborhood is finding all the little gardens, and walkways that folks create. The area is an intricate well kept treasure trove of nooks and crannies. The more you get out and explore the better — I’ve never had two sessions from the Back Bay or Beacon Hill ever look the same.

most photographed street in boston, acorn street

To see more of Jon & Tyson’s session click here.

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