Cuffing season is that magical time of year during the colder, winter months when people are more compelled to start relationships. It’s also a great time of year to snuggle extra close, you know, for warmth. We put together a sweet list of Trustees properties that offer the perfect place to take your date, your love, or even your special friend.

The Guest House at Field Farm – Williamstown

The Inn at Castle Hill – Ipswich

What is sexier than an overnight stay with your sweetheart? We have not one, but two. luxurious options for a special weekend away with your boo. Choose between our authentic mid-century-modern Bed & Breakfast in the beautiful Berkshires, where you can wake up to gorgeous views of pastoral fields and Mount Greylock, or snuggle up to stunning views over the salt marshes, sand dunes, and Atlantic Ocean at the Inn at Castle Hill in picturesque Ipswich. Whether it’s the mountains or the sea, this cuffing adventure will feel like a warm hug.

The Archives and Research Center – Sharon

What could be more romantic than a private tour of the Trustees Archives and Research Center? If you and your honey want to nerd-out over some really interesting history and artifacts, you can book a private appointment to visit our ARC and hold hands while learning about a plethora of interesting information from our ever-growing repository of research materials. From letters written during the Civil War to books inscribed by Ralph Waldo Emerson, to Trustees founder Charles Eliot’s scrapbook to ribbons for prize-winning pigs, you might fall in love even harder… with The Trustees.

The Old Manse – Concord

If historical cuffing season is a thing, we’re here for it. What’s more romantic than Georgian clapboard built on the banks of the Concord River in 1770? You can live out your poetic and fictional 19th century fantasies, as you and you boo imagine both Ralph Waldo Emerson and Nathaniel Hawthorne who both called the Manse home for a time: Emerson drafted his influential essay “Nature” in an upstairs study. Meanwhile, Hawthorne and his wife, Sophia, started their married life here. Plus, all the little nooks and crannies at the Old Manse are perfect for stealing kisses.

deCordova – Lincoln

We realize that deCordova Sculpture Park and Museum in Lincoln seems like an obvious choice for cuffing season. Who can resist a sweetheart selfie in front of the two black heart? Why stop there? We invite you to smooch next to every single sculpture in the park!. Are you up for the challenge? Make sure you dress warm and bring your chapstick/lipgloss/lipstick because it is chilly out there and those lips need protecting. Snuggling up in the cold is so much fun!

Jewell Hill – Ashby, Ashburnham, and Fitchburg

Do you feel like taking the next step in your relationship this cuffing season? One place you might want to consider if you’re planning to present your other half with a special gem to show your love, is Jewell Hill. Not only are we thrilled at the double entendre, but the views are absolutely spectacular. Start your visit off with a romantic hike to the summit through thickets of mountain laurel along the 0.6-mile Jewell Hill Trail, and when you reach the scenic overlook, look east over a landscape blanketed in forest; on days free of clouds and haze, you’ll see the Boston skyline 45 miles in the distance. That’s when you know it’ll be the perfect time to pop the question.

Long Point Wildlife Refuge – West Tisbury

Travel to the edge of the universe this cuffing season because in the wintertime, Martha’s Vineyard feels like a far away land. Visiting Long Point Wildlife Refuge in the winter is an otherworldly experience. Peaceful, quiet, romantic walks along the beach are the stuff that dreams are made of. Follow a two-mile trail, hand in hand, that leads through pitch pine-scrub oak forest, expanses of sandplain grasslands and shrublands, and sandy beach. Is there anything more romantic than traveling to a “remote” island in the winter to take a long walk on the beach?