Engagement and Proposal Locations in the Berkshires

If you're looking for a stunning spot to propose or take engagement photos in the Berkshires, you're in the right place! As someone who has recently explored these beautiful destinations west of Worcester, I can't get enough. It's an ideal location for couples who are looking for a unique way to pop the question or have your engagement session! Whether you are a history buff or a nature-loving couple there is something for you! 

"The Berkshires" refers to the range of hills in western Massachusetts that lie between the Housatonic and Connecticut Rivers. Just 2.5 hours from Boston and 3.5 hours from NYC, and provides a peaceful escape from city life. The area offers many outdoor activities, breathtaking views, farm-to-table food, and charming New England towns to explore. 

Why take Engagement Photos in the Berkshires?

While you know I love a Boston proposal or engagement session (you can read more here), I also can’t recommend the Berkshires enough! If you love the outdoors or just looking to do something different, this landscape creates a relaxed setting for your proposal or engagement session. City proposals can add stress with finding parking and crowds and let’s face it - that is just not for everyone!

A proposal or engagement session is usually your first time in front of the camera. It can be a little stressful with other people around who are watching during a high-stakes moment! Heading outside to any of the locations suggested below will be more calm and relaxed. Plus, there are fantastic restaurants and unique places to stay to make a weekend out of it!

Proposal & Engagement Locations in the Berkshires

Naumkeag

Naumkeag is a stunning historic estate a part of the Trustees in Stockbridge, MA, known for its beautiful gardens and grand architecture. This Gilded Age mansion features 44 rooms and extensive formal gardens, making it a unique location for proposals and elopements. The estate offers panoramic views, incredible gardens, and various seasonal events. Note that it is open seasonally, Thursday - Sunday. While photography is allowed, it is recommended that photographers or their couples are Contributing Level members of the Trustees before taking portraits. 

Ruins at Sassafras Museum

The Ruins at Sassafras Museum, located in the Berkshire Hills, provide a unique and romantic setting for proposals and engagement photos! It is like a secret property where you can wander and explore to get some truly unique photos. You can expect to find sweeping mountain views, ruins, a waterfall with a little bridge, hiking trails and so much more! The owner of The Ruins at Sassafras is incredibly kind and goes above and beyond for her visitors. Read more about a surprise winter proposal I captured on this property!

Mount Greylock

As the highest peak in Massachusetts, Mount Greylock offers breathtaking views for a proposal or engagement! I can attest that the views from the summit are truly spectacular. How could you not love being at the highest peak in Massachusetts?! I highly recommend planning to stay at the Bascom Lodge which also sits atop the summit just a short walk away. Read more about Becca and Justin’s intimate elopement here! 

The Mount - Edith Wharton’s Home

The former home of author Edith Wharton, The Mount in Lenox, MA, features a stunning historic mansion with beautiful gardens and woodland trails. This estate is perfect for a romantic and literary-themed proposal or engagement session. Photography is allowed for a small fee. They prefer this take place after hours so you would have the property all to yourself, which is well worth it! 

Afterward, I recommend you check out Frankies for an Italian meal in downtown Lenox. You can also stay at The Old Inn on the Green which is considered the number one historic inn in New England. 

Mass MoCA

MassMoCA is an incredibly unique museum for the artsy couple located in North Adams! This massive converted factory offers unique spaces filled with modern art installations, perfect for a creative proposal or elopement. Spend the day exploring the visits and grab some food at one of the nearby restaurants just a short walk away.

The Lakehouse Guest Cottages

The Lakehouse Guest Cottages on Pontoosuc Lake offer a waterfront setting for a proposal or engagement session. The serene lake views and lodge rooms for two create a perfect romantic escape.

Hiking Locations for Engagement Photos or Proposals in the Berkshires 

The Berkshires are filled with places to hike for private and intimate portraits out in nature. Tyringham Cobble and Bartholomew's Cobble are both Trustee's properties. They have similar landscapes for hikers. Bartholomew’s Cobble has beautiful mountain views! Other options include the Pleasant Valley Wildlife Sanctuary in Lexon or the Natural Bridge State Park in North Adams.  

Located right on the Massachusetts-Connecticut border, Campbell Falls State Park an ideal spot for couples who love nature and want to hike to a quiet, remote location. Proposing or taking engagement photos in front of their waterfall would be absolutely magical! It is open year-round and free to the public. 

Looking for more to do in the Berkshires? Check out The Mohawk Trail for pre-planned scenic driving routes that ensure you see numerous beautiful spots throughout the Berkshires.

Whether you're dreaming of a romantic proposal amid the fall foliage or looking for a unique engagement location, the Berkshires provides a diverse number of options to choose from! Reach out to Tamara Merri Photography as your photographer for your photographer in the Berkshires! 

xx,

Tam

Tamara Merri Photography

www.tamaramerriphotography.com