6 Unforgettable Proposal Locations in Cape Cod & The Islands

Author David Millette
Date Feb 15, 2021

After 135 years in the business, we know a thing or two about some of the best proposal locations around the area. You'd be surprised by how any of our engagement ring customers have bounced location ideas off of us to get our advice before popping the question! We've even gone so far as to write a few other articles about some of the best places to propose in Boston, the North Shore, the South Shore, and greater Massachusetts.

Well in the spirit of summer, we're finally announcing our picks for the best proposal locations in the Commonwealth's favorite summer spot... Cape Cod! This may have been the hardest one yet because there are so many great spots to choose from.

We're confident that you'll love these 6 romantic proposal locations though, so take a look and be prepared when you're ready to propose!

1) Sandy Neck Beach - Barnstable & Sandwich

sandy-neck-lighthouse-barnstable-massachusetts Most Romantic Proposal Locations in Cape Cod
Michelle Wiarda

When you hear the words Cape Cod, I bet you imagine beautiful natural landscapes, white sand beaches, and the occasional light house. Well, at Sandy Neck Beach, you will find all of this and then some. Located in Barnstable & Sandwich, Sandy Neck stretches 6 miles of ocean front and consists of 4,700 acres of dunes, maritime forests, and marshes.

My favorite thing about this beach is the number of fun summer activities that you can do here. If you have an off road vehicle, you can purchase a beach permit and drive right onto the sand. You should plan to stay late because beach bonfires are allowed after 7:00 PM and setting up a campsite to stay the night is allowed!

There are literally countless spots where you could propose at the beach, but I recommend the Sandy Neck Lighthouse (pictured above). Could you really ask for a more picture perfect setting than that?

2) Cape Cod Rail Trail - Dennis, Brewster, Orleans, Eastham, & Welfleet

Most Romantic Proposal Locations in Cape Cod Rail TrailMost Romantic Proposal Locations in Cape Cod Rail Trail Wood Bridge
Coastal Living || Coastal Living

Before cars were a common item for families to own, the railroad was responsible for bringing in almost all of the tourists and seasonal residents to Cape Cod. Once cars became more popular, the need for a railroad disappeared, and by the 1960's, the cars had stopped running and the idea to re-purpose the rail was born. The result was the Cape Cod Rail Trail, a 22 mile paved path where anyone is allowed to walk, roller blade, or bike from Dennis to Welfleet and everywhere in between.

Along the 22 mile trail, there's a whole lot to take in. Quaint towns, cranberry bogs, bridges, and coastal views are just some of the many sights you can encounter along the way. Plan out a place along the trail that you think would make for the perfect proposal, and take your special someone out for a ride.

3) Pilgrim Monument - Provincetown

Most Romantic Proposal Locations in Cape Cod Pilgrim Monument Provincetown
Pilgrim Monument

Everyone knows that the Mayflower landed at Plymouth Rock, but what you may not know is that they landed in Provincetown first and stayed for 5 weeks before setting off for Plymouth. To commemorate this historic event, the Cape Cod Pilgrim Memorial Association built this 252 foot tower to serve as a reminder of the role that Provincetown played in our country's founding.

The walk to the top of the tower takes about 10 minutes at a leisurely pace, and at 350 feet above sea level, this is a view that you are not going to want to miss. Take your loved one up to the top of the tower, and mark the beginning of your new lives together where the pilgrims once marked the beginning of their new lives in the new world.

4) Chatham Bars Inn - Chatham

Most Romantic Proposal Locations in Cape Cod Chatham Bars InnMost Romantic Proposal Locations in Cape Cod Chattham Bars Inn

For some, the Cape is all about living lavishly by the ocean. Well if that's the case for you, then the town of Chatham is the perfect spot, and there is no better place in Chatham than the famous Chatham Bars Inn. The beautiful inn and its friendly workers ensure that no matter who you are or where you're from you, will feel relaxed and at home here. In fact, it's so inviting that it's become a common hangout spot for locals looking to enjoy a few drinks or a nice meal.

Take your girlfriend for a summer retreat at the Inn, and enjoy all of its amenities. When you feel like the moment is right, take her to a spot you will want to remember, and pop the question. The best part about this is that the bar has a wide selection of celebratory cocktails to choose from, and you don't need to worry about driving anywhere after.

5) Brant Point Light House - Nantucket

Most Romantic Proposal Locations in Cape Cod Brant Point Light House Nantucket

At a not-so-staggering 26 feet tall, the Brant Point Lighthouse may not be the biggest or brightest on the Cape, but it is definitely one of the most famous. Brant Point is located right at the tip of Nantucket Harbor and has become the un-official welcome committee for people traveling to the island by boat or ferry. This well known lighthouse earned its spot in history as the 2nd lighthouse to be built in the US, although it has been re-built nine times since the original was put in place.

The lighthouse and Brant Point Beach are both a short walk from downtown, but surprisingly it isn't a high traffic area. Take your fiance-to-be for a walk around the beach and take some pictures by the light house. You can even go for a swim in the water, although I don't recommend it because the current can be strong and there is a good amount of boat traffic. Wait for the Steamship Authority ferry to get close and give the crowd a show by getting down on one knee and pulling out that sparkler. You're sure to get some applause from the passengers and who knows, maybe a touched onlooker will recognize you walking around town and tell your new fiance just how lucky she is.

6) Aquinnah Beach & Gay Head Cliffs - Martha's Vineyard

Most Romantic Proposal Locations in Cape Cod Aquinnah Beach Gay Head LighthouseMost Romantic Proposal Locations in Cape Cod Gay Head Cliff
MVY || 189 Market

Located on the western side of Martha's Vineyard, Aquinnah Beach is a place like no other and probably my favorite beach in the commonwealth. I say this because the beach is at the base of the Gay Head Cliffs, which are made of clay and give the beach a unique multi-color landscape that you won't find anywhere else. On top of the cliff sits the Gay Head Lighthouse, the first lighthouse on the island that served to warn sailors of the treacherous rocks nearby.

Aquinnah is a long stretch of beach that is perfect for walking and exploring the clay cliffs. Take your girlfriend on a stroll and admire the area's beauty until you find a place that you think makes a great proposal spot. This next line is very important to read so PAY ATTENTION TO THIS WARNING! Aquinnah is one of the country's last remaining nude beaches. This may not be apparent when you first get there as people tend to keep their clothes on in the heavily populated family area. As you walk down the beach, you can expect to see some nudity though, and if you aren't expecting it it could definitely throw you off your game when it's time to propose. With that being said, if you can look beyond this, I highly recommend that you take a walk to the end of the beach because the clay cliffs are incredible.

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