The 15 Best Places to Propose in Massachusetts

Find incredible proposal spots from the North Shore to Western Mass and beyond.
Couple holding hands on boardwalk in Massachusetts
Photo: Cavan Images / Getty Images
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by
Shelby Wax
shelby wax headshot
Shelby Wax
The Knot Contributor
  • Shelby is a contributing writer for The Knot covering all things weddings.
  • Shelby is a freelance writer for publications including Vogue, Over the Moon and Allure. She previously served as Senior Editor at Brides and Editor at Lonny Magazine.
  • Shelby graduated with a bachelor’s degree in English from Scripps College.
Updated Mar 04, 2024

If you're hoping to plan the perfect proposal for your partner, you might want to explore the state of Massachusetts. While Boston is a favorite location with many landmarks where you can get down on one knee, the best places to propose in Massachusetts are spread all across the state. From the beaches of Cape Cod to the farmland of the West to the coastline of the North Shore, there are plenty of unique proposal locations across the state.

According to Massachusetts-based engagement and wedding photographer Ricky Rodriguez, spring and fall can be some of the best moments to capture the state in its natural beauty. He suggests finding "a photographer who has photographed a proposal before to help you plan it a little" and "has photographed in lighting situations of the desired location" to ensure the best experience. We suggest looking for your ideal proposal photographer on The Knot Vendor Marketplace.

Ahead, find that perfect location with beautiful proposal spots in Western Massachusetts and along the North Shore and South Shore.

In this article:

Best Places to Propose on the North Shore

If you are looking to propose on the North Shore of Massachusetts, take a look at these great locations.

The Oceanview of Nahant

Make your way to The Oceanview of Nahant for a lovely coastal proposal. "At sunset, you get some beautiful light by the beach and there are a few walking trails that would be great for a proposal with the sunset behind," says Rodriguez. "Usually, there's not too many people around either to give you that intimate feel by the beach."

The Grafton Estate

While it requires a rental, The Grafton Estate is an incredible home with a private beach and garden in Manchester-by-the-Sea. "Sunset or close to sunset is fantastic for a proposal at The Grafton House," says Rodriguez. "You can go to the beach for the proposal or the beautiful garden on the property, which has a wonderful secret garden feel to it."

The Crane Estate

A historic seaside property, The Crane Estate is a classic New England mansion with lush acres of fields and a beautiful ocean view. "To organize a proposal there would be memorable, and it would be a wonderful experience doing portraits after," shares Rodriguez.

Beauport Hotel Gloucester

Stay right on the beach on the North Shore at the Beauport Hotel Gloucester. Pop the question in a luxury suite with an ocean view or head down to the sand for the big question.

Salem Waterfront Hotel

Fans of spooky szn would love to take a trip to storied Salem for a unique proposal. Get a room at the Salem Waterfront Hotel where you can enjoy views of the marina and have close access to downtown. You could even rent a boat to have your engagement on the water.

Best Places to Propose on the South Shore

See the following spots on the South Shore to get down on one knee.

World's End

A 251-acre park and conservation area, World's End is a lush green escape in Higham, Massachusetts. "The scenery is diverse and with a sunset proposal, the vista will be so beautiful as a backdrop," shares Rodriguez.

The Lighthouse Inn

Stay at The Lighthouse Inn to enjoy a beachside proposal at a resort with its own working lighthouse. The historic Cape Cod hotel even has its own cottages for newly engaged guests to enjoy a private escape.

The Nantucket Hotel and Resort

Take a trip out to Nantucket with your special someone to explore the beaches and get down on one knee. The Nantucket Hotel and Resort is the perfect spot to stay and enjoy its well-appointed rooms after your big moment.

The Provincetown Inn

Head to the iconic Provincetown for an inclusive, coastal retreat for your proposal. The Provincetown Inn is a historic waterfront hotel where you can pop the question with a view.

The Wauwinet

Have a luxurious experience at the waterfront resort The Wauwinet in Nantucket before proposing to your partner. The classic charm of the hotel and incredible dining options will help surround the special moment with an incredible vacation. The location could even serve as your future wedding venue.

Best Places to Propose in Western Massachusetts

A Western Massachusetts proposal will be a sure thing at these romantic places.

The Mount

Literary buffs will love getting proposed to at The Mount, the historic home of author Edith Wharton in Lenox complete with beautiful grounds and Italian-inspired gardens. "There is a pergola that provides views of the landscape beyond while framing views from the landscape to the garden within," shares Rodriguez of prime engagement spots. "There is also the 'Lime Walk' with a gravel pathway and lined-up linden trees on each side."

Valley View Farm

Get engaged at a working farm and cidery at the Valley View Farm in Haydenville, Massachusetts. "It is still a working farm but they have planners on-site that can help with planning a proposal," notes Rodriguez. You even can take photos with horses or amongst beautiful foliage in the fall.

Wheatleigh

Feel as if you're transported to Italy while remaining in the Berkshires at Wheatleigh. Rodriguez shares that a stunning fountain at the entrance and open green fields would serve as the perfect backdrops for a proposal. "Having a small dinner with family and friends at the Wheatleigh would complete a perfect day," he shares.

Quonquont Farm

Spend a day at the working Quonquont Farm where you can enjoy fresh food, pick your own flowers and arrange an idyllic proposal in nature. Photography is allowed on site for a small fee.

University of Massachusetts Amherst

Alumni of University of Massachusetts Amherst should absolutely consider a proposal at their alma mater. Find a special spot you loved back in college to get down on one knee.

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