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Ready to Pop the Question in Boston: Best Surprise Proposal Spots in the City of Boston

The biggest decision for a couple is the decision to get engaged, followed by choosing the absolute perfect ring. However, once those decisions have been made, the pressure turns to the perfect place to propose in Boston. Because it is one of the most special days of a couple’s joint lives, it will be romantic, memorable and perfect regardless of where it takes place. 

However, some proposal locations are prettier (and photograph better) than others.  Boston is full of beautiful, unique places to propose; there is a destination for every couple’s style and personality.  Boston is home to a historical monuments, luscious gardens, sporting venues and more that can provide the perfect backdrop for a perfect proposal.

The decision on where to propose can stem from a couple’s history together, a shared passion for an event or place or a desire for a new, romantic and unforgettable experience. Considering these factors, and for proposal photography purposes, the following is a list of some of Boston’s best surprise proposal locations. 

For those looking to woo with romance.  There is almost no spot in Boston more romantic than Top of the Hub. Located on the 52nd floor of the Prudential Tower, this restaurant provides the perfect backdrop – a bird’s eye view of the city – for a romantic proposal, complete with an elegant dress code, live jazz music and delicious food and cocktails. As an added bonus, in a busy restaurant, it is highly unlikely for the future fiancé to notice the surprise proposal photographer in the crowd.

For the couple that roots, roots, roots for the home team. There are very few sports venues more historical than Fenway Park, or fans more loyal than the Fenway faithful.  For couples that love to head to a game, sip on a cold one and take in the America’s pastime, a proposal at Fenway Park could be the perfect backdrop for a resounding “yes!”  Whether on the big screen, privately in the stands or outside on Yawkey Way, a Fenway proposal would be picture-perfect. 

For the couple that is one with nature. The Arnold Arboretum is 281 acres of nature that offers a beautiful, natural backdrop for a proposal. In autumn, the Arboretum is especially beautiful as it displays the bright reds, oranges and yellow leaves. Set up a picnic or stroll along the path toward Peters Hill.  This romantic scenery offers a perfect place to not only pop the question, but to capture the moment with a romantic, surprise proposal photography session.

For the couple that prefers a more private, intimate moment.  Most couples would not think that an engagement on the top of a parking garage is ideal; however, Kendall Square’s Green Garage’s rooftop is home to a secret garden.  Although luncheons and other events are often hosted here on weekday afternoons, the space is typically empty. This offers a peaceful, private engagement atop of the beautiful, bustling city.

For true-blue Boston natives.  While Acorn Street is often bustling, now known as one of the most “Instagram-able” spots in the city, the narrow Cobblestone streets lined by row houses is old-school Boston.  It serves as the perfect backdrop for couples that were born and raised in Boston and love its history. (Plus, what couple does not want that perfect engagement photo in a spot that tourists seek out almost solely for a photo session!)  As an added bonus, Acorn Street is located in Beacon Hill, which offers up a host of post-engagement celebration spots such as Toscano or The Hungry I.

A proposal should be truly special as it marks the beginning of the next steps of a couple’s lives together.  With a perfect Boston location for everyone, and a Boston surprise proposal photographer to capture the romantic moments, every couple with have a Boston engagement to remember.