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Boston Surprise Engagement Photography

7 Best Spots for Boston Surprise Engagement Photography

The endless charm of this historic city makes it the perfect place to propose! It is home to the historic Freedom Trail footpath, Paul Revere’s house, Faneuil Hall Market and the Union Oyster house— the oldest operating restaurant in the country.
Perhaps more important to Bostonites, however, is that it is also home to the Red Sox, historic Fenway Park, and the birthplace of the delicious Dunkin Donuts, located five steps in any direction from where you happen to plan your marriage proposal.
Besides its spirit and pride, Boston also boasts stunning scenery– from its red brick and cobble-stoned streets, to its townhouses, to the meandering Esplanade river pathway where runners and bikers turn out year-round to enjoy the scenery on the banks of the Charles. The Boston Common, easily accessible from the Esplanade, provides stunning views of the city’s historic center and hosts outdoor events during the summer months, offering countless creative proposal ideas.
And if the two of you love the ocean, take to the sea for your marriage proposal! With gorgeous Harbor Islands and nearby the picturesque Cape, a romantic sunset sail provides yet another fantastic option.

Of course, all the memories from your big day can’t speak for themselves.  Having a surprise engagement photographer nearby to discreetly capture that “Yes!” moment ensures that you’ll be able to enjoy your proposal in privacy, and share the event with family and friends after the fact.

We’ve put together a list of marriage proposal locations that are perfect for Boston surprise engagement photography:

The North End Engagement

The quaint North End neighborhood is historic Boston at its finest.  Take your special someone on a walk to the famous Mike’s Pastry for a casual vibe. Or, class it up with a complete dinner at one of the area’s many restaurants, like Bricco.  Afterwards, meander through the cobblestoned streets until you find the picture perfect spot to pop the question. Then head to one of the wine bars nearby for a bite and a celebratory post.  Salute!

Top of the Hub Proposal

Nothing offers spectacular 360-degree views and amazing dining quite like this luxury restaurant on the top floor of the Prudential Center.  Every Boston resident dreams of reservations at this coveted spot, as much for the views as for the amazing food.  Located in downtown Boston, near the happening shopping area Newbury Street, Top of the Hub delivers a star-quality experience.  Pop the question like a celeb by having paparazzi-style surprise engagement photography to capture the whole thing.  Afterwards, walk down Newbury Street for an incredible portrait session.

The Esplanade Engagement

The meandering pathway offers a spectacular panoramic view perfect for a sunset proposal.  A slice of the countryside with city views, the Esplanade is a picturesque place to pop the question.  Propose on the Boston side of the Charles to capture the waterways, trees and lawns.  Or propose on the Cambridge side for views of Downtown Boston in the background.  Perhaps your honey went to Harvard, and you’re a B.U. grad, so compromise with a symbolic proposal on the Longfellow or West Boston Bridge.  And if the two of you are fans of Venice, transform the Charles into Italy for the night with a romantic Gondola Ride.

The Boston Gardens Proposal

The historic center of Boston has countless picture-perfect locations great for creative proposal ideas.  Take a walk or a horse and carriage ride through the park, stopping to pop the question on the delicate blue footbridge in the Boston Gardens. Regardless of the time of year, this location offers stunning views and a truly romantic proposal moment.  Class it up by having a picnic blanket, a dozen roses, and a bottle of champagne waiting at a nearby for the two of you to enjoy before, during, or after you drop to one knee.

Acorn Street in Beacon Hill Proposal

Located in the posh and historic Beacon Hill neighborhood, “the most photographed street in Boston” is the perfect place to pop the question and a natural fit for your surprise engagement photography shoot.  One block of immaculately maintained, untouched colonial houses set on a cobblestoned incline makes for an incredible backdrop for your romantic proposal.

Historic Pub Proposal

Boston is all about craft beer.  Take a private tour of the Sam Adams or Harpoon Breweries, or head to Doyle’s, the oldest bar in Boston, for an authentic proposal moment or impromptu engagement party with friends and family.  Whether you’re visiting from out of town, or revisiting one of your favorite haunts, this original proposal idea is truly one of a kind.

Fenway Park Engagement

You can’t get more Boston than Fenway.  While it might not be located downtown, the over 100-year-old baseball park is undoubtedly the heart of the city.  If the two of you are native Bostonians, or just huge Red Sox fans, this is definitely the proposal place for you.  Propose right before you sing “Sweet Caroline,” then join friends and family afterwards at the Right Field Roof Deck for an impromptu engagement party.