You’ve arrived in Kent. Roll down your windows and smell the freshly-cut hay meadows. After driving over the covered bridge onto route 7, meander along the Housatonic River and land in the center of town.
5:00 pm: Snack at 109 & CHEESE. After a long drive you deserve a snack,right? Luckily 109 & Cheese is open “late” (this is the country, so yes, 6:00 is late). It’s a no-brainer, get the grilled cheese. The combination of Gruyere, Cheddar and Toma grilled on fresh sourdough bread is possibly the best grilled cheese you’ll ever have (only made better by their suggested addition of wild mushrooms). Grab some cheese while you’re there, the selection changes weekly and is perfectly curated every time.
6:15 pm: Check in at INN AT KENT FALLS. Voted best Bed and Breakfast in the state by Travel and Leisure 3 years in a row. Like staying in the country house of close friends. They have a pool and yoga studio.
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.
9:00 am: THE VILLAGER. Have breakfast at the Villager, a small town diner with all the classics. You can sit at the bar, a booth or outside. The Villager is owned and run by the Hernandez family from Oaxiak, Mexico ( sidenote: they open
for dinner only one night a week (Tuesday) for authentic Mexican cuisine. Book early. It is always sold out.). You have to ask for Omar’s special hot sauce for your breakfast burrito.
10:00 am: KENT GREENHOUSE. A lot of daily visitors to RT Facts seem to be on their way to or from the Kent Greenhouse. People travel far and wide to get their plant-fix here. They offer items you may not expect, mature espalier apple trees, and a large variety of unusual perennials…like their seasonal pumpkin tree! How many people do we send there to get some of the unusual plants we have clustered around the front doors of RT Facts for themselves?
10:30 am: RT FACTS DESIGN AND ANTIQUES. Housed in two Kent locations. You can see the monumental zinc eagle (ready for flight) and huge granite millstone table at the Main Street location from Route 7 just south of the light. The Main Street shop has been a secret source for designers for 25 years. What draws them is the mix of sleek contemporary pieces, designed and made right here, paired with interesting antique pieces. The weird and wonderful abound.
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 big white elliptical gesso mirrors. With three buildings and garden spaces, the Main Street shop is buzzing. The team makes much of the on-trend furniture on site. Next, head over to the 7,000 square foot museum-like showroom with soaring ceilings. It is two blocks away but don’t skip it. 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 seeing the “dinosaurs” (actually reconstructed cow and horse skeletons).
11:15 am: PANINI CAFE. Try a scoop of the grapefruit or mango gelato at Panini café across the parking area. Very refreshing!
11:30 am: JAMES BARRON GALLERY., ECKERT FINE ART, OBER GALLERY. Just outside the door of RT Facts Gallery are the spaces of three world-class art dealers. Come on the Second Saturday of fair-weather months and you will find them all open late, pouring wine and hosting musicians into the evening. More galleries can be found in town, including the acclaimed MORRISON GALLERY.
12:30 am: 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 Michael, the mixologist. The small plates menu changes daily. This is our favorite part. Treat yourself to a little tasting menu and order a few to share while you taste the beers on tap, many of them local. Try “Tempus” by OEM Brewers for which they snagged a rarely available keg. Feeling more exotic? Go for “Voodoo Ranger” or any one of their other unique selections.
Feeling more like a gourmet deli? Try JP GIFFORD’S on Main Street. Sit outside (very pup-friendly, like most of the town) and fill up a jar at the kombucha bar while waiting for some truffle fries, the scent of which probably pulled you into their shop. This deli & market has become a Kent standard, with creative twists on traditional sandwiches & a bakery offering fresh croissants and more. Take it to go and picnic at Kent Falls 10 minutes up the road.
1:00 pm: KENT WINE AND SPIRIT. Just north of JPG’s and 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 that picnic.
1:30 pm: PICNIC AND HIKE AT KENT FALLS. Cross the little covered footbridge over the stream and pick a table with a view of the falls. After lunch hike up the rustic woodland staircase that winds around the falls offering key overlooks. The secret is when you get to the top, walk up and around to a walking trail on the other side to descend. Approx. 45 min.
3:00 pm: MICHAEL TRAPP. Take a 15 minute drive up the Housatonic and you’ll find yourself at the Cornwall covered bridge. Pass over, and take the second left over the train tracks and you’ll arrive at Michael Trapp Inc. Perched on a steep, hidden overlook above the Housatonic River, Michael is nothing short of genius. We’d describe his place as theatrical masculine-romantic. More like set-design than visual merchandising. Featured in all of the major magazines, including World of Interiors, Michael has established an international reputation for originality.
4:00 pm: KENT FALLS BREWERY. This is the only farm brewery in Connecticut. Look out for the chickens and sheep as you walk through. Visit for a tour and tasting, hosted by one of the founders of the brewery. There’s truly no experience quite like smelling the hops and seeing the fields, which makes a taste of their Apricot Gose (cold, straight from the keg) even more refreshing.
5:30 pm: KINGSLEY TAVERN.
Kingsley Tavern, another Kent-rooted, family-run business that makes you feel at home. The beef cows are raised at the same home where the recipes are conceived. Order the pork belly Saigon sandwich with kimchi and enjoy it on the front porch with a River Road Martini and watch the slow pace of Kent.
7:30 pm: Sunset drive around LAKE WARAMAUG. It’s almost a waste of time to try to describe. Just let the orange and pink water, reflecting the 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.
8:00 pm: MAYFLOWER INN. The Mayflower Inn in of itself is an entire weekend destination. With an incredible spa and grounds for walking and snowshoeing. This is a luxurious place to spend the night in a big four-poster bed suite.
8:00 am: 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.
9:00 am: HIKE THE PINNACLE. More vigorous than Kent Falls, the Pinnacle is an approximately 2 mile hike. Park at the off-street parking on Christian Street in New Preston and come down the same way you went up. Your hard work is rewarded when you reach the flat, rocky outcropping on top; an awe-inspiring 360 degree view of the surrounding area which includes Lake Waramaug, New Preston, Washington, and even Massachusetts in the distance.
1:00 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 stones-throw away. Take a peek into the back room and see the gleaming tanks where the milk is being processed.
1:30 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.