10 Best Places to Propose in Massachusetts (2023)

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by Suzanne Sachs  5 min read



Massachusetts is full of perfect places to propose. Whether you and the person you love are enthusiasts for beautiful gardens, beaches, parks, natural scenic beauty, or good food and wine, there’s a beautiful spot to create a lifetime of memories. This guide describes some of the best places in Massachusetts to ask that special person to marry you.


In this guide we will explain the following:

  • Romantic Locations in Massachusetts
  • Cape Cod
  • The Bershires
  • Harvard Yard - Cambridge
  • Beautiful Beaches
  • Nantucket Island
  • Martha's Vineyard
  • Outdoor Locations to Propose in Massachusetts
  • Bridge of Flowers - Shelburne Falls
  • Boston Red Sox Baseball Game
  • Wineries
  • Castle Hill on the Crane Estate
  • Mount Graylock
  • Boston Public Garden
  • Best Places to Propose in Massachusetts


Romantic Locations in Massachusetts

1. Cape Cod

Enjoy a sunset proposal on one of Cape Cod's many beaches, like Race Point Beach or Nauset Light Beach. Cape Cod has a vibrant arts and culture scene, with numerous art galleries, theaters, and museums. You can plan a proposal around a cultural event or explore the local arts scene.


2. The Berkshires

Propose at a cozy bed-and-breakfast in the Berkshires, or on a scenic overlook like the Bash Bish Falls. The Berkshires are beautiful year-round, offering the chance to propose amid vibrant foliage in the fall, a winter wonderland in the snow, or lush greenery in the spring and summer. The changing seasons can add an extra layer of significance to your proposal.


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3. Harvard Yard - Cambridge

If you're both academically inclined, propose in the historic Harvard Yard, perhaps under the John Harvard Statue. The Yard is also known for its stunning architecture, with iconic buildings like Widener Library, Memorial Church, and Massachusetts Hall. These beautiful structures provide a visually captivating backdrop for your proposal.


Beautiful Beaches

3. Nantucket Island

  • Explore the charming streets of Nantucket, and propose by the picturesque Brant Point Lighthouse or on one of the island's beautiful beaches. Nantucket offers numerous beautiful beaches, including Jetties Beach, Surfside Beach, and Madaket Beach. Proposing on a secluded beach at sunset or under the stars is a dream for many couples.

  • best-places-to-propose-massachusetts


    4. Martha's Vineyard

    Take a stroll through the colorful streets of Oak Bluffs or propose on the cliffs of Aquinnah overlooking the ocean. The island's sense of seclusion and escape from the mainland can create an intimate and private setting for your proposal, making it feel like your own little paradise.


    Outdoor Locations to Propose in Massachusetts

    Massachusetts is full of romantic gardens, beaches and wineries. These are some especially romantic locations for a proposal on a romantic walk, viewing lakes or enjoying a glass of wine or champagne in a secluded spot for the perfect proposal.

    5. Bridge of Flowers - Shelburne Falls

    This charming bridge is covered in blooming flowers and makes for a unique and romantic proposal spot.


    6. Boston Red Sox Baseball Game

    Proposing at a Boston Red Sox baseball game can be an exciting and memorable experience, especially if you and your partner are fans of the team or enjoy sports together.


    7. Wineries

    Massachusetts is home to several picturesque vineyards and wineries that can provide a romantic and memorable setting for a marriage proposal. Nashoba Valley winery offers beautiful vineyards, orchards, and a rustic setting, making it an ideal spot for a proposal. You can explore the vineyards, enjoy a wine tasting, and propose amidst the scenic beauty. Hardwick Vineyard & Winery is set against the backdrop of rolling hills, providing a serene and tranquil atmosphere for a romantic proposal. You can enjoy a wine tasting and then find a secluded spot to pop the question.


    8. Castle Hill on the Crane Estate

    Propose at this beautiful mansion overlooking the ocean in Ipswich. The Crane Estate offers stunning gardens and landscapes.


    9. Mount Greylock

    Hike to the summit of Mount Greylock, the highest peak in Massachusetts, for stunning panoramic views to make your proposal extra special. The mountain is surrounded by lush forests, cascading waterfalls, and pristine wilderness, creating a serene and picturesque setting. The combination of natural beauty and fresh mountain air adds to the romantic atmosphere.


    10. Boston Public Garden

    Take a swan boat ride in the serene setting of the Public Garden and propose in front of the iconic bridge. The iconic Swan Boats of the Public Garden offer a romantic and whimsical element to your proposal. You can consider proposing on one of these iconic boats as you glide across the pond.


    Best Places to Propose in Massachusetts

    While it can be tempting to get wrapped up in elaborate proposal plans, sometimes the very best way to ask the question is a classic, heartfelt, on-one-knee moment. Whatever you and your soon-to-be fiance or fiancee enjoy, Massachusetts has beautiful and memorable places to propose. Make one of these romantic locations your special place by proposing with the perfect vintage engagement ring.



    Vintage Engagement Rings For Everyone:

    No matter which era is your favorite, these time-honored rings have a rich history and individualized character and will continue to have a timeless beauty and elegant appeal that is part of a legacy to pass on to future generations.

    Find The Perfect Engagement Ring:

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    Suzanne Sachs

    Suzanne has always believed vintage rings can change lives. She's been in the jewelry industry for over 35 years, working with vintage jewelers, diamond dealers, diamond cutters, and gemologists. Suzanne started Artdecodiamonds in 2000 and understood the demand for vintage rings throughout the world. She ultimately started VintageDiamondRing.com in 2014, and understands each vintage ring is a reflection of you – your history, your relationships, your style, your elegance and is honored to have the opportunity to help you showcase your flair in a unique and exquisite way.


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    Contact Suzanne

    If you love vintage or eco-friendly jewelry please feel free to contact Suzanne or browse our collection of eco-friendly vintage engagement rings.


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