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Some of the best places to propose marriage in Massachusetts

Spring signals new beginnings in more ways than one, marking the first National Proposal Day of 2024 on March 20 — just a day after Vernal Equinox.

The semi-annual occurrence came about, the story goes, after a man’s cousin broke up with her boyfriend because he would not propose, according to Shane Co. and many other jewelers’ websites trying to promote the ring-focused “holiday.”

To remind others there is always time to propose and commit to your true love, the man established National Proposal Day, which typically aligns with vernal and autumnal equinoxes — times of balance.

Figuring out the best place to pop the question may be a challenge for some people. Tamara Arnold, Worcester-based photographer and owner of Tamara Merri Photography, said things to consider when planning a proposal are lighting, sentiment, experience and foot-traffic.

“Most couples try to get a private spot,” said Arnold. “Most proposals are all surprise …. It all depends on how people want to be surprised.”

She said it’s “all about the view,” and finds water locations tend to be popular.

“Boston Seaport is great because you can walk around and get versatile scenes,” said Arnold, though as a photographer seeking to record that special moment, “it’s all about the lighting.”

Berkshire-based photographer and owner of Chelsea Proulx Photography, Chelsea Proulx-Bordonaro said “anywhere with a view and having a moment to themselves,” makes for a memorable proposal.

“When the person proposing spills their heart out, and tells them what they love about (the fiancé to be) it’s more romantic,” said Proulx-Bordonaro. “It goes by so fast.”

She said some of the most memorable and special proposals are the ones that the couple are most excited for, adding proposers who take the extra time to plan the occasion and surprise their partner are the most exciting to photograph.

Proulx-Bordonaro partners with the company Berkshire Picnics to set-up a spread for couples at the proposal location.

“The ones that walk down to the picnic and wonder who it’s for, then realize ‘oh that’s for me?,’ it’s sweet,” said Proulx-Bordnaro.

She said the picnic option also allows for the couple to sit-back and relish in the moment for a little bit.

Arnold said “no place is a bad place to propose,” as long as it’s meaningful to the couple.

For those looking to make the occasion extra-special and add meaning to new spaces, MassLive offers nine highly recommended proposal destinations known for “checking off all the boxes.”

Central Mass. proposal spots

New England Botanic Garden at Tower Hill, Boylston

New England Botanic Garden at Tower Hill offers proposers an opportunity to pop the question while taking the fiancé-to-be, to “experience the wonder of plants at a botanic garden in the heart of New England,” according to its website.

This 200-acre garden includes conservatories, gardens, a café and views of the Wachusett Reservoir and was named “Best Botanic Garden in the U.S.” by “TravelAwaits” in 2023.

For those considering proposing here, Arnold said couples can expect a “beautiful greenhouse,” in addition to eight gardens throughout the property.

Wachusett Reservoir Old Stone Church, West Boylston

Old Stone Church at Wachusett Reservoir is recognized by Long’s Jewelers of Peabody as a “perfect” proposal spot for those who love autumn in New England.

It is situated alongside the banks of the Wachusett Reservoir, offering visitors a chance to propose along the water front or within the privacy of a historically rich, stone building.

According to Whiting Photography, Old Stone Church is a “great location because you can get so much variety without going very far.” It features large, glassless windows and a wealth of natural light.

It is on the National Register of Historic Places and is no longer an active house of worship, allowing couples an opportunity to explore the 19th-century building.

Mt Greylock mountain

An aerial photo of Veterans Memorial Tower on top of Mount Greylock.

Western Mass. proposal spots

Mount Greylock, Adams

Mount Greylock in Adams is recognized by special event photographers as a proposal destination due to its 3,491 ft. elevation and scenic overlook.

“The view is beautiful,” said Proulx-Bordonaro. “You don’t always get to see that view, and it can become a destination you go back to over and over again.”

According to Mass.gov, on a clear day, guests can see as far as 90 miles away. Visitors have the option of hiking or driving to the top.

The Mount proposal destination

The Mount offers a variety of scenic views including a large, green-lawn space and an early 20th century mansion.Chelsea Proulx Photography

The Mount, Lenox

The Mount, in Lenox, is a proposal destination rich with history and features versatile scenery. This location is known best as the home of the late American author and fashion designer Edith Wharton.

The early 20th-century mansion features a variety of rooms to explore with the option of strolling the expansive estate grounds, which includes a garden of ivy and another of flowers.

Berkshire-based photographer Proulx-Bordonaro said The Mount can be a favored proposal space, as it offers “more of an experience,” opposed to a stagnant location.

“Just walking through history,” said Proulx-Bordonaro, “where you feel inspired.”

She added walking through the estate gives the proposer time to “work up the courage,” and gain “inspiration,” before popping the question.

The Mount proposal destination

The Mount is home to the late author and fashion designer, Edith Wharton. The estate offers views of an early 20th-century mansion as well as scenic greenery.Chelsea Proulx Photography

Naumkeag, Stockbridge

Naumkeag is a property of The Trustees of Reservations. It is a public garden and historic home in the heart of the Berkshires.

The 48-acre estate is regarded as an “architectural masterpiece,” according to The Trustees official website, and hosts an annual Daffodil & Tulip Festival from April 19, until May.

Proulx-Bordonaro said the estate possesses a “really sweet and very New England charm,” while also offering mountain views, adding The Trustees of Reservations have scenic destinations fit for proposals throughout the state.

Naumkeag

The Naumkeag is located on 40 acres of land in Stockbridge and has 44 rooms. The Trustees of Reservations photo

Cape Cod proposal spots

The Knob, Falmouth

The Knob is a scenic destination in Woods Hole described as a “major attraction to the public for its nature walk, birding, marsh, coastal bank and its spectacular views of Quissett Harbor and Buzzards Bay,” by Salt Pond Bird Areas Sanctuaries Inc.

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Long’s Jewelers lists The Knob as one of seven scenic proposal locations in Massachusetts, referring to the destination as a small peninsula offering “360 degrees of beautiful scenery,” and described by Cape Cod Xplore as providing “a breathtaking setting for a perfect proposal.”

Boston proposal spots

Harrison and Anneke proposal

The Mount in Lenox, is a proposal destination in Western Mass. offering versatility and garden views. It also has a rich history as it is the home of late author Edith Wharton.Chelsea Proulx Photography

Acorn Street

Acorn Street is an iconic and often-photographed street in Beacon Hill. Many photographers have portfolios dedicated to capturing proposals in this location.

“It’s one of the most photographed streets in the country, and a very popular spot in Beacon Hill,” Arnold shares on her official photography website.

“It is a quintessential old Boston street; quaint narrow alley of row houses on a cobblestone lined street.”

Acorn Street is a private way governed by a neighborhood association which retained ownership of the street to prevent the City of Boston from paving it in the 1980s.

Fan Pier Park

Fan Pier Park in Boston is a popular proposal destination given its “quintessential New England (feel),” said Arnold.

This location features water-front views of Boston Harbor as well as the iconic Boston skyline.

It has become recognized for its photogenic atmosphere by many Massachusetts-based photographers, with some creating entire portfolios comprising images of couples who popped the question in this very spot.

“The Seaport is great to walk around and get versatile scenes,” said Arnold.

Charles River Esplanade

The Charles River Esplanade is considered a popular proposal location, in part because of its water-front views and a large vegetation space just beyond the city.

“It’s a really active location,” said Proulx-Bordonaro. “It’s a place where people can get away from the city but still be in it.”

She said it is far enough away from the city that visitors have a “really big green space,” but also have a view of the city lights and life.

Sailboat rentals are another option for those looking to pop the question on the water.

Did we miss THE best proposal spot in your neck of the state? Email Dallas Gagnon at dgagnon@masslive.com.

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