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Celebrate Life’s Milestones in The Berkshires

Posted on February 26, 2024Written by Nichole C. Dupont on behalf of 1Berkshire
Updated on March 08, 2024

A white man and woman smile at each other beneath wooden beams decorated with flowers. It is a wedding alter. She wears a long lacy white dress. He wears and light gray suit. She has dark brown hair falling down her back. He is bald. Behind them is out of focus greenery.

If there’s anything that the last four years have shown us, it’s that we want to connect with friends and family.

Whether it’s a long overdue family reunion, a wedding that has been in the works for years, or a well-deserved retirement party, the Berkshires is the place for celebrations and connecting with loved ones. 

Memorable Weddings

Your perfect day, big or small, should be about you and yours. Leave the rest to the professionals. Beginning with an event planner, such as the award-winning, creative team at Only In My Dreams events, who are official members of the National LGBT Chamber of Commerce. And for the wows of lighting, sound, and specialty entertainment, look to T. Warner Artists. For images, Tricia McCormack Photography offers two decades of experience capturing unforgettable moments in the Berkshires. And then there are the details, which for a wedding are everything. Mahaiwe Tent or Classical Tent and Party Rentals  are great options as your one-stop source for tableware, tents, linens, and more. Let Thistle ‘n Thorn Floral create custom floral arrangements for your venue, while the amazing chefs and caterers at the Marketplace build a delicious menu, not to mention a truly unforgettable cake. 

Chesterwood Studio is a white stone house with many glass windows. A fountain is in front in a green and flowery garden and lawn.

Beautiful Settings and Stays

There are so many milestones to celebrate life’s seasons, and with the seasons as a backdrop, unique properties in the Berkshires offer incredible views, venues, and experiences. Grand historic estates, like artist-haven Chesterwood, is perfect for larger events, while places like the Porches Inn at MASS MoCA and the Devonfield Inn in Lenox offer intimate luxury for elopements, friend retreats, and private gatherings. If you’re looking for a special homebase for a family reunion or multigenerational gathering, the Lakehouse Guest Cottages of the Berkshires in Lanesborough offers seven private cottages and is centrally located to the region’s cultural attractions. Sometimes, just being together is the goal for a special occasion. The Berkshire Farmhouse, an 1850s property surrounded by gardens and wooded mountains, is ideal for uninterrupted family time. The Freeman, a newly renovated Sheffield estate complete with a private tennis court and pond access (with kayaks), a game room, and expansive gathering spaces, is a haven for multi-generational gatherings.

The Freeman's backyard with lounge chairs on a sunny day overlooking a blue sky and trees.

The Unforgettable Details

Start and end your special occasion with hassle-free travel. There are several modes of transportation to and from the Berkshires for groups and for individuals from major airports, though you’ll want a car to get around the county if you plan to explore. And before you and your loved ones take your leave, refreshed and filled with memories, consider a special memento. Customize your special occasion with 413 Shirts, or take a bit of the region with you thanks to the Berkshire-inspired scents of Soma’s Aromas. Also, the Lanesborough Local Country Store proudly carries locally-sourced artisan gifts, snacks, and beverages. Across the street, you’ll find Inspired Creations, an artesian retail gift and home décor shop that hosts 50 vendors.

We can’t wait to help you celebrate in the Berkshires!

Funded, in part, by the Massachusetts Office of Travel & Tourism

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