36 Hours in Litchfield County (winter)

36 Hours in Litchfield County (winter)



You’ve arrived in Kent.  After driving over the covered bridge onto route 7, meander along the Housatonic River and land in the center of town.

5:00 pm: Stop for a hot chocolate or cappuccino at 45 ON MAIN by the railroad tracks. Perhaps you decide on Thai or bubble tea instead.  Choose something special from the case of gourmet chocolates made on site. Known for their unique truffles, try deciding between the popular sea salt, champagne or kahlua flavors.  Maybe go outside the box and try bacon, masala chai, or coconut lime. Peruse the gifts and goodies including nut-free and sugar-free options. Breathe in the rich smells and feel yourself unwind!

6:30 pm: KINGSLEY TAVERN another Kent-rooted, family-run business that makes you feel at home. The beef cows and veggies are raised here. Order the pork belly Saigon sandwich with kimchi and enjoy it with one of their signature cocktails.

7:00 pm: Dinner at FIFE N’ DRUM.  A long-time Kent fixture, a visit to the Fife is not just about good food. They make a Caesar Salad table-side that keeps people coming back. There is usually live music on Friday nights. It has been a meeting place for creative types for decades.  Sit by the fire with a hot toddy or Irish coffee.


9:00 am:   Have breakfast at WILSON'S. They make their own bread and that means killer breakfast sandwiches. Make sure you get a side of broasted brussel sprouts. Grab a seat by the fire and have a green smoothy.  

10:00 am: RT FACTS DESIGN AND ANTIQUES has been a secret source for designers for over 30 years. What draws them is the mix of sleek contemporary pieces, designed and made right there, paired with interesting antique pieces. There are deep marble bathtubs, 20′ high stone mantelpieces, and big museum cabinets filled with unusual treasures. It all looks fresh when mixed in with leather tables, gleaming steel bases and white elliptical gesso mirrors.  The team makes much of the on-trend furniture in the local workshop and moves it into the 7,000 square foot museum-like showroom with soaring ceilings. This location has the “wow” factor. Sit in the oversized marble throne chair and gaze up at the big polished steel mobile floating above. Kids love the seek-and-find challenge sheets. Come on the Second Saturday of fair-weather months for the KENT FLOWER MARKET on the front steps. 

11:00 am:  KENISE BARNES, CRAVEN CONTEMPORARY, CAROL COREY FINE ART Just outside the door of RT Facts Gallery are the spaces of three excellent art dealers. The acclaimed MORRISON GALLERY is just north on Main Street. 

12:00 pm:   MAIN STREET KENT.  Check out the boutique style shops offering local artisan work, gifts, and clothing in the welcoming small town atmosphere that is Kent.  Duck into the charming HOUSE OF BOOKS and pick up a book on the Appalachian Trail that passes through town.  This wonderful bookstore is one of the last independent bookstores left in Connecticut. Next door is a delightful tiny market called WOODFORD'S that sells local produce and baked goods. Just a few paces down the sidewalk is HERON GALLERY where one can find pottery, stylish kitchenware, artisan clothing, and a delightful children’s nook. 

1:00 pm:  SWYFT. Time to recharge. At Swyft you will feel you have been transported to a beautiful lodge in the Norwegian woods.  Sit at the bar and chat with the mixologist. The small plates menu changes daily. This is our favorite part.  Treat yourself to a little tasting menu while you taste the beers on tap, many of them local. Try “Tempus”, by OEM Brewing. Feeling more exotic? Go for “Voodoo Ranger”, or any one of their other unique selections.

1:30 pm:  KENT WINE AND SPIRIT. More than just a wine shop, Kent Wine and Spirit is a gem. With 80 single malt scotches and 135+ types of beer and ales in stock, it’s the ideal place to feel adventurous and try something new. On the weekends you’ll find tastings of wine or specialty liquors, accompanied with insightful quips about the drinks’ origins or uniqueness from the charismatic staff. Grab a bottle of wine for a picnic. 

2:00 pm:  KENT FALLS.  Cross the little covered footbridge over the stream and take in an ice-covered wonderland view of the falls.  Conditions permitting, hike up the rustic woodland staircase that winds around the falls offering key overlooks.

2:45 pm:  MOHAWK MOUNTAIN.  A hidden gem in the foothills of the Berkshires, Mohawk mountain is run by the inventors of snow-making equipment.  They know what they’re doing and have a scenic, state park-adjacent setting to do it in. Stay for night skiing.

7:00 pm: Dinner at FERN in Lakeville. It's a serpentine drive along scenic Housatonic River and past the sprawling campus of Hotchkiss School. Fern is likened to Balthezar in SOHO. Fresh Italian entrees and a sassy bar.  


8:00am : On your way through WASHINGTON DEPOT, stop at WASHINGTON PARK ASSOCIATION, a postage stamp-size park on your left and admire the 46′ long “Currents”, a river sculpture in granite by MARK MENNIN. You will want to stop and lay in the ripples and run your palms along the smooth, hand-polished, undulating surface. Walk across town and be sure to peak into the windows of GEORGE HOME. They won’t be open this early, but looking in is worth the walk.

8:15 am:  HIDDEN VALLEY EATERY. Sit at the counter and chat with the chefs and the locals. Chances are, they helped harvest or live near one of the farms from which the ingredients in your meal were sourced. The dining room is like a forest with branches of birch trees on the walls. Order the breakfast pizza with a sunny-side-up egg on top and one of their daily fresh-squeezed juices.

9:30 am:  Drive around LAKE WARAMAUG. It’s almost a waste of time to try to describe. Just let the morning sun show you. This drive is imperative in the fall for “leaf-peepers”, the local term for visitors that come to town for the beautiful fall foliage.  Ready for more winter sport? Strap on a pair of ice skates and soar over the winter ice of the lake. You can access the lake from Lake Waramaug State Park located on the west side.

11:00 am:  Explore the shops in NEW PRESTON. PRIVET HOUSE for home goods and really beautiful brushes of every variety. PERGOLA a boutique of unusual plants and gifts for the horticulturally-inclined. PLAIN GOODS has great brands of cozy sweaters. 

12:00 pm:  HOPKINS INN WINERY.  Overlooking Lake Waramaug is the Hopkins Inn Vineyard and Winery.  The farm turned vineyard has been in the family for 225 years. Sign up for a tour, pick up a gift for your wine enthusiast friend (and yourself) at the gift shop, or simply sit back and enjoy sampling award-winning wines at the wine bar in the Hayloft barn.  Pop over to the Inn for an amazing meal with a German flair. Make a mental note to come stay here for a getaway weekend next summer. The view for patio dining is breathtaking.

2:00 pm:  ARETHUSA. Before heading back to the City, take a detour past Mount Tom Pond to Bantam where you can find a trio of shops featuring ingredients from the Arethusa farm. (Think it’s unusual that RT Facts has two shops in the same town? Arethusa has three.) Looking for a snack and a caffeine boost? Stop by Arethusa a Mano for a pastry and a latte made with milk from their cows. Feeling more than peckish? Arethusa Al Tavalo is a dairy farm-to-table restaurant drawing inspiration from classic Italian cuisine with local resources in mind. Want to see where the magic happens? Step over to Arethusa Dairy store, where they are scooping freshly churned ice cream. They sell cheeses and other products fresh from the farm a stone’s throw away. Take a peek into the back room and see the gleaming tanks where the milk is being processed.

3:00 pm:  BANTAM BREAD. Just down the hill is Bantam Bread. Get the light and crispy-edged buttermilk biscuits to put your cheese on. Buy some store-made granola to take home and some fresh dog cookies for your buddy.  Head back south replete!