Travel Inspiration By A Pro Trip Designer

Winvian – A Classic Charmer in Connecticut

Friend Of A Friend Consulting, Travel Tips



Country Charm in Litchfield: The historic main house of Winvian built in 1775

Country Charm in Litchfield: The historic main house of Winvian

For a quick birthday getaway, my husband and I traveled an hour north to the rolling hills of Litchfield county in northwestern Connecticut. Known for its prized antique stores, wealthy creative-type residents and relaxed (unpretentious) atmosphere, Litchfield is a bucolic destination ripe for tucked-in, romantic stays amid woodland. So, in other words, it’s ideal for a birthday or anniversary celebration, particularly so since 2007 when the 113-acre compound resort, Winvian, opened its doors. And what doors they are! Comprised of eighteen individually designed cottages scattered around the sizable land, no one dwelling is even remotely alike. In fact, so distinct are they that it’s absolutely requisite that one take a gander at the website and view each of the stunningly unique offerings prior to booking. My personal favorites are saved for Friend of a Friend clients, but I can safely assure you, dear reader, that they are all worthy of a special night stay.

One of my favorite cottages on property

One of my favorite cottages on property

Chock full of charming colonial architecture and a small main street lined with the odd haberdashery shop and cozy cafes, Litchfield makes for a nice pit-stop should you want to get off campus during the day. However, I highly recommend you return for dinner, as the Chef’s freshly grown (onsite) produce and organically sourced main courses are a treat not to be missed. And did I mention the wine list? I could have taken the heavy book with me to bed and poured over it for an hour, if only to make a wish list of must-try wines before dying.

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Much has been written about the funky compound and its demonstrably high-end product – rooms go roughly for $1200 a night and come with all-inclusive and a la carte options, however, what struck me far more than the luxury trimmings and even the eye-popping architecture and zen-like Spa, was the utter devotion paid to the guest experience from the owner, Margaret Smith and her son, Win Smith III. Having been treated to their company on a few occasions during our overnight stay, I am confident in declaring that any guest of theirs would be hard pressed not to feel an instant kinship with them. So welcoming and engaging are they that to it feels almost odd to pay a bill at the end of your stay. Yet, all the while, their company was anything but intrusive. We were only ever approached when already in a relaxed and jovial state – enjoying a raucous game of shuffleboard after dinner or fully satiated after breakfast, dawdling over a second cappuccino. I confess, I already look forward to returning to Winvian, if only to hang out with the Smiths again.


155 Alain Road

Morris, CT 06763

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Posted in: Friend Of A Friend Consulting, Travel Tips

Published by Meg, Friday, April 12, 2013 1 Comment

about meg

About Meg


Meg is the founder of luxury travel consulting company, Friend of a Friend Consulting. Her three books, Italian Hideaways, Caribbean Hideaways and England's Hideaways are published by Rizzoli. Passionate about travel, hotels and wine, she continues to write freelance travel pieces and is currently pursuing a Masters in Wine through the WSET.

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The opinions expressed on this blog are solely my own and do not reflect separate business relationships with the subject. Whenever posts are supported financially, they are designated as such.