Boston's 8 Best Hidden Gem Proposal Locations

Author Sam Hussey
Date Feb 15, 2021

After the ring, choosing a location is one of the most important and difficult proposal decisions you'll have to make. You want it to be perfect! Something special. Something she'll remember forever.

This is the moment the rest of your life changes, the one you'll be telling your children and grandchildren about. You need a location worthy of that importance. So to help you out we've come up with a list of 8 unique Boston proposal locations that will be sure to blow her mind.

Make the day even more memorable by popping the question at one of these hidden gem locations in Boston.

1) The Reflecting Pool at the Christian Science Plaza

boston reflecting pool proposal

Stretching for 670 ft across the Christian Science Plaza in Boston's Back Bay area, the Reflecting Pool is a point of calm in the center of the busy city. The intricate architecture of the Original Mother Church and the lines of Linden trees bordering the pool make for a more intimate setting ideal for any proposal.

Just a short walking distance from Symphony Hall, Boylston Street, and Newbury Street, the Reflecting Pool provides a unique proposal location just minutes away from some of the most romantic restaurants in Boston!

Because the pool is drained during the Winter season, this would be the ideal location for a Spring or Summer proposal.

2) Christopher Columbus Park Trellis

Christopher Columbus Park Trell Proposal
via North End Waterfront & Matt Conti Photography

A short walk from Boston's North End, you'll find Christopher Columbus park. Among the rose garden and amazing waterfront views, the Christopher Columbus park trellis is one of the park favorites.

New LED lights have been installed to replace the failing fixtures of 1975. Year round white lights illuminate the trellis creating a warm, romantic glow at night. Every year blue and white holiday lights (see above) illuminate the trellis through the holiday season.

Because of the amazing location, the area often gets crowded. Consider going early in the morning or late in the afternoon to avoid crowds and take advantage of the trellis' gorgeous lighting

3) Week's Footbridge over the Charles River

weeks footbridge proposal

Week's footbridge crosses Boston's famous Charles River connecting Cambridge and Allston. Walk along this bridge and let the scenic views set the stage for your proposal. Lights illuminate the bridge at night making it the perfect spot to pop the question any time of day!

4) Nashoba Valley Winery

nashoba winery proposal

This breathtaking hilltop orchard will blow your significant other away. This up and coming area is the perfect destination for any romantic night out. The intimate feeling the country setting gives coupled with the location's outstanding wine collection and gourmet food is everything you could want for your big night.

Get away from all the city hustle and bustle, wind down, and savor every last moment of the night in Massachusett's apple country.

5) Courtyard of the Isabella Stewart Gardner Museum

Courtyard Isabella Gardner Stewart Museum proposal
via Heidi Finn Photography

At the heart of the Isabella Stewart Garden Museum, an interior courtyard filled with flowers and sculptures creates an intimate display for works of art.

Known as the most romantic building in Boston, the courtyard broke the mold of American Museum models in its time, lighting up the galleries, staircases, and windows to create a warmer setting.

If you and your significant other love art, history, and culture there couldn't be a more perfect spot to have this life-changing moment.

6) Memorial Drive, Cambridge MA

boston skyline memorial drive proposal

If you want the best view of Boston's skyline to backdrop your proposal, head to Memorial Drive and watch the city light up the night sky from across the Charles River. The bike path provides a safe and easily accessible place to walk along the river and take in the scenery.

A proposal setting doesn't have to be expensive or exclusive to be romantic. The beauty of Boston's skyline lighting up the dark night sky turns the by-day bike path into an intimate setting for two.

7) Blue Hills Skyline Trail, Blue Hills Reservation

Blue hills skyline trail proposal
via Cheryl Suchors Photography

If you love the outdoors and being active, this unconventional proposal idea may be exactly what you're looking for! Located in North Randolph, MA, Blue Hills Skyline Hiking Trail includes numerous summits with breath taking panoramic views. Along this 12 mile trail beautiful meadows, ponds, and rocky hills lead you to outstanding views of Boston. Want to see other perfect hiking trails for a proposal? Check out these highly recommended trails to find the one that's right for you.

This location is also perfect for dog lovers. Make the night even more memorable by bringing your four-legged family member along to help with the proposal. Also check out some of our favorite ways to include your dog in the proposal.

8) Winter Island, Salem MA

winter island salem proposal
via Stanley Slysz Photography

About an hour north of the city, Salem provides the ultimate spot for a romantic proposal by the ocean. On top of the hill on Winter Island, let this flawless sunset (or sunrise) do all the work.

Listening to waves crash against the shore and watching orange-pink colors fill the sky over the Island's quaint
lighthouse. It's the kind of scene you would read about in a romantic novel. She'll be swept up in the romance of
this perfect proposal spot.

Still haven't found the right ring yet? We're here to help! Contact us or make an appointment with one of our diamond specialists to find the engagement ring of her dreams.


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