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 Stephen Grant Photography
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Commonwealth Ave Engagement Proposal

BOSTON ENGAGEMENT PROPOSAL PHOTOGRAPHER


As with every session, both the client and photographer daydream to a certain extent in advance as to what our time together will be like. We might form preconceived ideas as to how the pictures will look, or when planning a surprise proposal, you’ll likely visualize the big moment in your head to prepare for how it might unfold. Having a vision and plan in place is crucial to a successful engagement proposal. But once the session starts, destiny takes the wheel, and that’s when it’s best to let go of how you dreamed it would happen and instead lean into the moment as it was meant to happen, unexpected surprises and all.

For this nighttime engagement proposal along Boston’s Commonwealth Ave, we thought the rain would pass and deliver clear skies, but that was not to be.  What started as a light rain quickly grew into a steady drizzle, and although the Totes umbrellas I brought along provided sporadic shelter, the only way for the three of us to really let loose and comfortably shoot was to get a little wet.  And I’m so glad we did!  Thank you, Mother Nature, for ignoring our pleas for a dry evening and instead delivering a shiny, magical night beyond what any of us could have conceived in advance.

After D+C’s engagement proposal under the twinkle lights of Commonwealth Ave, their families popped out of the shadows to deliver a second surprise. We then strolled over to Boston Public Garden, Beacon Hill, and Acorn Street to continue the celebration in some of Boston’s most popular engagement session locations.  The weather kept most people indoors, so we enjoyed plenty of privacy in what are typically very busy spots.  If you are someone who is looking for a private engagement proposal in one of these well-known Boston locations, scheduling your surprise for later in the evening is definitely the way to go.

Thank you, D+C, for your joyful flexibility and embracing the element of surprise. Proposing to your partner at night in Boston is always a beautiful choice, and I’m so glad we had the chance to work together!

Boston Public Garden Engagement Proposal | Stephen Grant Photography
Commonwealth Ave Engagement Proposal | Stephen Grant Photography
Boston LBGTQ Engagement Proposal | Stephen Grant Photography
Boston LBGTQ Engagement Proposal Photographer | Stephen Grant Photography
Commonwealth Ave Engagement Proposal At Night | Stephen Grant Photography
Commonwealth Ave Engagement Proposal | Stephen Grant Photography
Boston Engagement Proposal Photographer | Stephen Grant Photography
Boston LBGTQ Engagement Proposal | Stephen Grant Photography
Commonwealth Ave Twinkle Lights Engagement Proposal | Stephen Grant Photography
Beacon Hill Engagement Proposal | Stephen Grant Photography
Beacon Hill Engagement Proposal | Stephen Grant Photography
Boston Public Garden Engagement Proposal | Stephen Grant Photography
Commonwealth Ave Engagement Proposal | Stephen Grant Photography
Boston LBGTQ Engagement Proposal Photographer | Stephen Grant Photography
Commonwealth Ave Engagement Proposal At Night | Stephen Grant Photography
Boston LBGTQ Engagement Proposal | Stephen Grant Photography
Commonwealth Ave Engagement Proposal At Night | Stephen Grant Photography
Boston LBGTQ Engagement Proposal | Stephen Grant Photography
Commonwealth Ave Engagement Proposal | Stephen Grant Photography
Boston Engagement Proposal Photographer | Stephen Grant Photography
Boston Public Garden Engagement Proposal At Night | Stephen Grant Photography
Commonwealth Ave Engagement Proposal | Stephen Grant Photography
Boston Public Garden Engagement Proposal | Stephen Grant Photography
Boston Public Garden Engagement Proposal | Stephen Grant Photography
Beacon Hill Engagement Proposal | Stephen Grant Photography
Boston LBGTQ Engagement Proposal | Stephen Grant Photography
Boston Engagement Proposal Photographer | Stephen Grant Photography
Commonwealth Ave Twinkle Lights Engagement Proposal | Stephen Grant Photography
Boston LBGTQ Engagement Proposal | Stephen Grant Photography
Boston Public Garden Engagement Proposal At Night | Stephen Grant Photography
Acorn Street Engagement Proposal | Stephen Grant Photography
BOOK YOUR ENGAGEMENT PROPOSAL
ENGAGEMENTS // PROPOSALSStephen GrantFebruary 21, 2026BEACON HILL ACORN STREET ENGAGEMENT PROPOSAL, BOSTON COMMONWEALTH AVE ENGAGEMENT PROPOSAL, COMMONWEALTH AVE ENGAGEMENT PROPOSAL AT NIGHT, COMMONWEALTH AVE NIGHTTIME ENGAGEMENT PROPOSAL, ACORN STREET ENGAGEMENT PROPOSAL, BOSTON PUBLIC GARDEN ENGAGEMENT PROPOSAL, BOSTON PUBLIC GARDEN ENGAGEMENT PROPOSAL AT NIGHT, COMMONWEALTH AVE TWINKLE LIGHTS ENGAGEMENT, BOSTON LGBTQ ENGAGEMENT PROPOSAL, BOSTON LGBTQ ENGAGEMENT PHOTOGRAPHER, BOSTON LGBTQ WEDDING PHOTOGRAPHER, BEACON HILL ENGAGEMENT PROPOSAL, BOSTON SURPRISE ENGAGEMENT PROPOSAL PHOTOGRAPHER
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WEDDINGS // ELOPEMENTSStephen GrantFebruary 7, 2026CRANE ESTATE WEDDING, CASTLE HILL CRANE ESTATE WEDDING, CASTLE HILL WEDDING, CRANE ESTATE STEEP HILL BEACH WEDDING, STEEP HILL BEACH WEDDING, IPSWICH WEDDING PHOTOGRAPHER, BOSTON WEDDING PHOTOGRAPHER, NEWBURYPORT WEDDING PHOTOGRAPHER, BOSTON BEACH WEDDING

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Stephen Grant Photography
100 Bennett Hill Road,
Rowley, MA, 01969,
United States
978-225-0036 stephen@stephengrantphotography.com
Hours

FAMILY // SENIOR // WEDDING PORTRAIT PHOTOGRAPHY

Stephen Grant is an on-location, natural light wedding and lifestyle portrait photographer in Rowley & Newburyport, Massachusetts, who specializes in family & children’s portrait photography, weddings & engagements, elopements, high school senior portraits, maternity & newborns, headshots, and personal branding & commission work.

Serving the North Shore, Greater Boston, Southern New Hampshire, and available for travel to destinations beyond.

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