The 6 Most Romantic Proposal Locations In The South Shore

Author David Millette
Date Feb 15, 2021

After 135 years of helping Bostonians get engaged, we've heard quite a few proposal stories. We know a thing or two about planning the perfect proposal and have a long list of amazing places to propose.

We want to pass along some of this wisdom and make sure that when you pop the question it's a day that she will never forget. We've already filled you in on our favorite places to propose in Boston, the North Shore, and greater Massachusetts. Now it's time for the one we've all been waiting for, Boston's South Shore!

Ask anyone from Massachusetts about the South Shore, and they'll probably tell you about incredible day trips to the area's many hidden gems. There's just something about this coastal escape that draws Bostonians south when the warm weather comes out.

With so many great places to visit, it can be hard to pick one favorite spot. So we had to pick six because we know they're all amazing places for the fairy tale proposal she's been waiting for.

1) World's End - Hingham

Most Romantic Proposal Locations In The South Shore World's End Hingham
The Trustees

If your partner is a fan of the outdoors, they'll absolutely love visiting World's End in Hingham. The park was designed by famous landscape architect Fredrick Law Olmstead, who is best known for designing New York's Central Park and Boston's Emerald Necklace Parks. Worlds End spans 251 acres of coastal landscape and offers visitors 4.5 miles of tree lined carriage pathways to hike on. Enjoy the coastal scenery and views of Boston's skyline until you find a the perfect spot to drop down to one knee.

Be warned that World's End does have a $6 admission fee. This is a small price to pay to preserve the beauty and history of the land, but we don't want you to be surprised when you show up!

2) Webb Memorial State Park - Weymouth

Most Romantic Proposal Locations In The South ShoreMost Romantic Proposal Locations In The South Shore
Carols Views Of New England || North Weymouth

Webb Memorial Park was opened in 1980 after the government decided it no longer needed to use the land as an underground missile storage facility. Although the park is on the mainland, it is considered to be a part of the Boston Harbor Islands, because of its coastal landscape. Walk around the parks 36 acres and take in the breath taking views of Hingham Bay and the Boston Skyline. As you can see in the pictures above, there's plenty of benches to have some alone time with a view... sounds like one of these could be the perfect spot to propose if you ask me!

3) Jerusalem Road - Cohasset

Most Romantic Proposal Locations In The South Shore
City Data

If you're not the type of couple that likes to go on hikes, suggesting that you go to a romantic coastal park "just for fun" might be a dead giveaway that you're about to propose (especially if you've kept her waiting). If this is the case for you, you may be interested in going on a coastal drive down Cohassets Jerusalem Road instead!

If you're unfamiliar with Jerusalem Road, it can be easily defined by two of its features: beautiful coastal views and luxurious beach houses. Roll the windows down and make your way down the coast until you find a look out that looks like the spot you'll want her to remember forever. You can even take it a step further by having friends or family waiting at a look out to share the big moment with you.

4) Great Blue Hill - Milton

Most Romantic Proposal Locations In The South Shore
City Data

Just 10 miles outside of Boston, the Blue Hills Reservation covers 6,000 acres of land and is home to more hiking trails and wild life than you can take on in one day. A fun fact about the reservation, it was once home to the Native American tribe Massachusett, which translates into "people of the hill." Hmmmmm Massachusett... sounds familiar.

The Great Blue Hill is the tallest within the reservation and makes for a great day trip. I recommend heading over to the Blue Hill Observatory to take in the view and learn what landed this building on the National Register of Historic Places. With so many acres to explore, there's countless spots to pop the question. Go scope it out, and plan your hike accordingly.

5) Quincy Quarries Reservation - Quincy

Most Romantic Proposal Locations In The South Shore
Joe's Retirement Blog

Living in Boston, there's so much graffiti around that I hardly even stop to take it in anymore. It almost feels like spray paint and city buildings just can't exist without the one another. In Quincy, street artists have put the skyscrapers on hold and have found a new favorite canvas, the old quarry. Normally I'm not a fan of defacing nature, but after seeing some pictures of the work, I can appreciate it for the art that it is.

Take your special someone to climb the rocks and check out all of the cool art that can be found throughout the park. I won't tell you to spray paint "Will You Marry Me" on the rocks because its illegal... but if someone were to do that I'm sure it would make their fiance-to-be very happy.

5) Quincy Quarries Reservation - Quincy

Most Romantic Proposal Locations In The South Shore
Mike Sleeper

The Powder Point Bridge is a half mile long and connects the main land to Duxbury Beach. Once in the Guinness Book of World Records for being the longest and oldest wooden bridge, Powder Point is a local favorite and tourist attraction during the summer months. If your loved one is a fan of quaint coastal charm, then this might just be the perfect place to propose.

Take her for a beach day and be sure to walk across the bridge on your way there. When the moment is right, stop and ask her to be yours. Knowing how popular the area can get, you'll likely have a crowd cheering for your success after she inevitably says yes. She'll probably start cheering too when she realizes that she gets to take her first picture with the ring in such a beautiful location!

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