A Litchfield Hills BFF Getaway Last Updated: September 2019

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Is it your turn to organize the next girlfriend’s staycation? We’ve got you covered with this itinerary for a perfect Litchfield Hills BFF (Best Friends Forever) weekend getaway! No planning required; this itinerary has it all. Here’s where to stay, shop, dine, and play in beautiful Litchfield County. Have fun!

Hopkins Inn, Warren

Step one in planning your weekend away is to choose the ideal accommodations. The Hopkins Inn is the quintessential country inn, located in Litchfield County’s epicenter on Lake Waramaug! Charming rooms, unforgettable Austrian dining, and views that will take your breath away. Kick back, have a glass of wine and relax. Prefer to walk and catch up? Enjoy the 7ish-mile walk around the lake and take in some of the most superb homes you’ve ever seen!

Winvian Farm, Morris

Extra special BFF weekend away, is it? Is somebody turning 40/50/38? You only live once! Winvian is about as unique and special a place to stay as they come. It’s tucked away in Morris and starts to cast its spell on you the moment you drive through the gates. Each accommodation is as original as the next and you can choose between the Library, Beaver Lodge, Helicopter, or seventeen other luxurious cottages. Enjoy some of the finest of dining at their seed-to-table restaurant, and don’t forget to check out the unbelievable spa!

R. Derwin Clothiers, Litchfield

Shopping time! Head over to Litchfield on 202 and take a stroll along West Street, facing the Litchfield green. Visit R. Derwin Clothiers for classic with a twist clothing, made from the purest of fabrics. Touch your way around the store and admire their displays of classy outfit suggestions, all with a little something unexpected. Whatever you treat yourself to will be in your wardrobe for years to come!

LuLu The Face Company, Litchfield

Staying in Litchfield, walk across the green and check out LuLu—The Face Company, inside the newly refurbished town jail! LuLu custom blends perfect makeup just for you. Stop guessing, stop buying the wrong thing, and get the correct makeup once and for all! Doesn’t a foundation that is light, airy, and luminous with sunscreen expertly matched to your skin sound perfect? Our kind of shopping. 

Arethusa al tavolo, Bantam

A local favorite (we poll everyone we meet), Arethusa al tavolo will serve you a meal you will not soon forget. Dinner, lunch, or a smaller bite or breakfast across the road at Arethusa a mano, your taste buds are going to be satisfied beyond their wildest dreams. Be sure to put a stop in Bantam on your weekend itinerary.

Kent Barns, Kent

For one-stop culture, shopping, and good eats in the lovely town of Kent, head over to Kent Barns. Make sure you stop at a few of the world-class galleries and soak up some art and culture. Good for the soul! Kent Barns is home to three amazing art galleries. Modern, Contemporary, American, European, and Russian artwork are all represented. Also within Kent Barns, you’ll find House of Books, which is a joy of a place to stop and browse. You’ll find interesting titles from smaller presses, New York Times bestsellers and everything in-between. Prepare to lose yourself in a good book!

Swyft, Kent

While you are in Kent, stop for lunch at Swyft, Kent’s newest restaurant and bar. Already known for their wood-fired pizzas and farm fresh small plates, Swyft has a really great modern-tavern vibe going on. With James Beard Award-nominated chef Joel Viehland at the helm, be prepared for a fantastic dining experience.

Sunset Meadow Vineyards, Goshen

No trip to Litchfield County is complete without visiting one of the vineyards for a wine tasting. Enjoy the scenic drive to Goshen and stop at Sunset Meadow Vineyards in Litchfield County’s "Highlands". There, you can toast good friends and good getaways with one of their 15 varieties of wine, or a Merlita (a wine slushy). Cheers!

Pics: Lora Karam/ Words: Bev Canepari