Top 7 Hikes For Proposals In Massachusetts [Boston Proposal Series]

Author Cristina LaPenna
Date Feb 15, 2021

For people who love the outdoors, the natural side of Massachusetts is as charming as it gets. From the hills of the Berkshires to the open spaces just outside of Boston, people take to the many reservations and mountains to relax and enjoy the great outdoors. Hiking is an easy and fun way to enjoy the outdoors during any season - Which makes it the perfect way (and one of the most popular ways) to ask your significant other for their hand in marriage.

Together with The Trustees, we've created a list of the best hikes to propose in Massachusetts. With locations all over the state, the hikes range in difficulty but all provide both a picturesque view and one-of-a-kind proposal experience. Take a look at the best hikes and where to pop the question, as recommended by The Trustees expert staff:

Hurlburt’s Hill - Bartholomew’s Cobble

Ashley Falls, Sheffield, Massachusetts || Moderate Hiking

Hurlburt’s Hill - Bartholomew’s Cobble - Longs Jewelers Hike ProposalPhoto Courtesy of R. Cheek

The best place for a proposal in the Southern Berkshires is on top of Hurlburt’s Hill at Bartholomew’s Cobble. The amazing panorama is inspiring and a girl couldn’t possibly say no surrounded by such beauty. The Trustees suggest a picnic followed by the picturesque proposal.

Monument Mountain Summit

Great Barrington, Massachusetts || Moderate Hiking

Monument Mountain Summit - Long's Jewelers Hike ProposalPhoto Courtesy of R. Cheek

If she loves to hike, then nothing beats the top of Monument Mountain, one of the Trustees favorite 'special places' from their many hikes. Try to schedule your proposal around sunset and start the rest of your life together with a gorgeous view.

Quaboag River - Quinebaug Woods

Holland, Massachusetts || Moderate Walking

Quaboag River - Quinebaug Woods - Long's Jewelers Hike ProposalPhoto Courtesy of J. Dillard

Quinebaug Woods in Holland offers a secluded, almost private proposal spot. Get a little more adventurous and lead your significant other out to the great rock on the Quaboag River. It is just a ¼ mile easy hike to get to, so you won't have to worry about losing the ring in the woods along the way!

Holt Hill - Ward Reservation

Andover & North Andover, Massachusetts || Easy-to-Moderate Hiking, Strenuous in Places

Holt Hill - Ward Reservation - Long's Jewelers Hike Proposal
Photo Courtesy of T. Reichard

Holt Hill is a great little hike that can bring you through open fields and even pass a rare quaking bog, but as you finally ascend on the hill, a picturesque view of the Boston skyline and the rolling hills will take your breath away. There are solstice stones where you can sit your loved one and get down on one knee to make it official.

Noanet Peak - Noanet Woodlands

Dover, Massachusetts || Moderate Hiking, Strenuous in Places

Noanet Peak - Noanet Woodlands - Long's Jewelers Hike Proposal
Photo Courtesy of R. Cheek

Although just about every summit that the Trustee's recommended is the perfect destinations for popping the question, Noanet Peak at Noanet Woodlands, Cedar Hill at Rocky Woods, or the peak at Noon Hill top the list. Make a day trip out of your proposal to hike one of these summits. If you both love to hike and go often, your loved one will never suspect a thing!

Peaked Mountain Summit

Monson, Massachusetts || Strenuous in Places

Peaked Mountain Reservation Summit - Long's Jewelers Hike ProposalPhoto Courtesy of K. McMahon

The summit of Peaked Mountain Reservation would also be a grand spot to propose. This reservation lies amid one of the most pristine, undeveloped areas of the state, with broad views of rural and forested landscapes in every direction. A 45 minute medium-strenuous hike to the top offers a 3-state panoramic view from Mount Wachusett to Vermont’s Green Mountains from the 1,227-foot summit.

Planters Hill - World’s End

Hingham, MA || Moderate Hiking

Planters Hill - World’s End - Long's Jewelers Hike ProposalPhoto Courtesy of J. Beller

Planters Hill on World’s End in Hingham overlooking the Boston Skyline is a very popular proposal spot, as is Westport Town Farm on the hill overlooking the agricultural fields and the scenic Westport river. The Trustee's tell us that they know people who have proposed at both spots, so either location is guaranteed to get a "yes" from him or her!

Do you have the perfect hike proposal in mind, but still need the ring? Contact us or make an appointment and one of our specialists will be more than happy to show you our extensive collection of diamond engagement rings in Boston and beyond!

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