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Where to Propose in Cape Cod

Modern Couples Guide to Proposing Places to Propose
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Cape Cod, a beautiful coastal area in eastern Massachusetts known for its lovely coastline, charming towns and idyllic accommodations, is a perfect place to plan a proposal in the spring and summer months. Reserve a room at a romantic B&B, such as the Cranberry Inn in Chatham, put some bubbly on ice and find the right moment to pop the question.

The cape is actually divided into four areas — Upper Cape, Mid Cape, Lower Cape and Outer Cape — and composed of 15 separate but nearby towns. The Cape Cod Travel Guide says, “Cape Cod’s 15 towns are not unlike siblings: metaphorical brothers and sisters, sharing some qualities, yet remaining refreshingly different.” Here are 12 of the best places to propose in Cape Cod.

1. Chatham Band Concert at Kate Gould Park

Step back in time by spending a beautiful summer evening listening to the Chatham Band play a free Friday night concert in Kate Gould Park. The concerts have been a Cape Cod tradition since the late 1940s, and they are scheduled every Friday at 8 p.m. from June 28 to August 30. Pack a gourmet picnic dinner, bring a blanket and dance with your sweetheart under the stars. During a slow song, draw your partner close and propose with a stunning diamond engagement ring.

2. Hiking Trails

If you’re not sure where to propose in Cape Cod, look no further than the great outdoors. Cape Cod has miles of trails designed just for cycling. Rent bikes from a local shop, pick your favorite trail and hit the road, biking leisurely along the coastline, through lush wooded areas or through picturesque towns. Stop for a break at a scenic lookout point and ask them to marry you!

3. At a Hyannis Sound Concert

Start your evening at Pisces, an intimate and romantic restaurant, for an early dinner of fresh local seafood or rib-eye steak (save room for the dessert wine and the Pisces toasted almond joy sundae). After dinner, head out to see an unforgettable acapella concert from the group Hyannis Sound (formed each summer by a group of some of the most talented college acapella singers in the country). Once you get back to your room after a wonderful evening and it’s just the two of you again, propose with a gorgeous diamond engagement ring and pop the champagne.

4. Herring Cove Beach – Provincetown

Travel to the tip of the Cape and spend the Day in Provincetown at Herring Cove Beach. Explore the vibrant town, and enjoy a relaxing day laying on the warm sand. There is nothing like a proposal at the beach to make a memorable trip to the Cape!

5. Highland Light – Truro

When exploring Truro, MA, we recommend taking a walk to the Highland Lighthouse. The sprawling lawns, and beautiful views make it a picturesque choice for a romantic wedding proposal.

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#throwbackthursday to the fall on the cape

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6. Lighthouse Beach – Chatham

Lighthouse beach is a must visit during your day in Chatham, MA!  A beautiful, sandy beach at which you can spend the day swimming in the ocean, squishing your toes in the sand, and proposing to the love of your life!

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Chatham, MA

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7. Nauset Beach – Orleans

Your partner will think it’s just another day at the beach – little do they know, you have planned the perfect proposal at Nauset Beach! Walk the length of Nauset Beach, and when the moment is right, take your partner’s hand, and present the wedding ring you have carefully selected for them!

8. Pilgrim Monument – Provincetown

Enjoy this piece of history, and the picturesque location of the Pilgrim Monument in Provincetown, MA. The towering structure is could be in the distant background of your proposal, or you could stand beneath the monument after having enjoyed exploring it’s history.

9. Race Point Lighthouse – Provincetown

Take a walk around the lighthouse or spend the night at the Race Point Lighthouse for a quaint experience. When thinking of the original purpose of a lighthouse (to be the beckoning light for those who were out to see to look to as the guiding light home), we can’t help but feel this is a wonderfully romantic location for two people, who have fallen in love and want to spend the rest of their lives together.

10. Sandwich Boardwalk – Sandwich

Picture this – walking hand in hand down the sandwich boardwalk, watching the sun fall behind the horizon, turning the sky a medley of warm colors (reds, pinks, oranges, yellows and purples dancing together as the sun sets). This is a romantic, intimate location that allows you to enjoy the natural beauty of the day as you bask in the excitement of your engagement!

11. Scargo Tower – Dennis

Climb to the top of the Scargo tower at sunset for a beautiful backdrop to your wedding proposal. As the sun sets on another beautiful day at the Cape, get down on one knee, and ask your partner to marry you!

12. Quissett Harbor & the Knob – Falmouth

Start your day at Quissett Harbor, and embark on the 0.9 mile trail to the Knobb! This oasis is known as the perfect location for a nature-filled day – from nature walks to bird watching, from marshes to coastal banks, and spectacular views of Quisset Harbor and Buzzards Bay, you will not be disappointed with a day spent at The Knobb.

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These two hired me on for thier wedding, and with the package they bought they got an engagment session with it …. then Covid-19 had other plans for humanity and things have been lessened and larger gatherings of course have been halted. I give it to Vinh and Meghan for having such a great energy and outlook for the love they share and still being so happy just to be together with all that is going on around us. I look forward to working with you guys more and for both wedding celebrations you will likely have now ! #engagementphotos #engaged #couplegoals #love #savethedates #capethings #capecod #capecodphotographer #capecodphotography #theknob #quissettharbor #falmouthma #portrait #portraitphotography #portraitphotographer #nikonphotography #nikonphotographer #covid19

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Do you have a great tip on where to propose in Cape Cod? Share in the comments!

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