Christopher Columbus Park Proposal in Boston | Robert & Ashley

Updated: Nov 2, 2023

man proposing to girlfriend under the trellis at Christopher Columbus Park in Boston

Christopher Columbus Park Proposal

Robert reached out to me to share the exciting news that he wanted to propose to his girlfriend of four years, Ashley, and was looking for a photographer. Since they both live/work in Boston he definitely wanted to propose in Boston. Originally we talked about the idea of him proposing in Boston Seaport along the Harborwalk (like this Seaport proposal here), but ultimately he decided he wanted to get on one knee under the trellis at Christopher Columbus Park as they love spending time in the North End. Christopher Columbus Park is right between Boston's Financial District and the Boston Harbor Waterfront which makes it the perfect location for walkability to get from bars and restaurants to more scenic photo spots like the wharf.

If you're looking to propose to your person and are deciding what the right spot is for you, check out my 12 places to propose in Boston blog!

Since it was early January, and pretty chilly, we had a perfect overcast day and the benefit of not many people hanging around or walking through the trellis. In the summer, the trellis is covered with gorgeous greenery weaving through all the slotted openings. In the winter, the city decorates it with blue twinkle lights and wreathes. So cute!

Robert and Ashley popped into a nearby bar for a drink while I arrived at the spot and prepared for their arrival. I had Robert share his location with me so as they made their way to the park, I got ready in the perfect position, ready to capture him dropping to his knee. Ashley immediately said yes (obv!) and everyone in the area cheered!! I think part of proposing in public is so exciting because all the bystanders really add to the energy of the moment!!

Related Blog: Acorn Street Proposal

After making sure Ashley's makeup was still on point and no tears ruined her makeup, we started off their little engagement session by popping a bottle of Veuve to celebrate and venturing around Christopher Columbus Park. I absolutely love the view of Boston's Custom House Tower from here!!! It makes the perfect backdrop for some urban, romantic engagement photos.

North Boston Engagement Session

I always give my couples the choice for whether they'd want to take some engagement photos after the proposal or if they just want to celebrate together sans camera. It's such an emotional event and sometimes it can be difficult to really be in the moment and process all the feelings when there is a camera documenting everything. They decided they wanted to continue and I'm so glad because having an engagement session right after a proposal is the BEST!!! The emotions are always so high so it's easier to document the true connection couple's have in a more documentary style way.

We also did another engagement session for them later on in the summer on the beach!

Christopher Columbus Park engagement session with Boston Custom House Tower in background

boston harbor engagement session in north end boston

After a little while we headed to the quintessential North Square Park for a few more cute photos in one of their favorite North End spots. After photos, Robert and Ashely walked to dinner at Prezza where Robert surprised his new fiance with a party with all their family and friends to celebrate their engagement!! Now that's what I call a perfect start to the next chapter in their love story.