The Litchfield, CT List

The center of Litchfield, Connecticut, is a postcard of a small town. It is quintessential New England, a Nancy Meyers dream, and still very much a hidden gem. It’s charms pulled my husband Kevin and me away from Manhattan, first as a weekend escape, and then as full time residents.

We’ve lived in Litchfield for nine years. After our wedding, my husband and I were looking for a house outside of New York City to escape to. While visiting one of my clients in Merryall, a small area of New Milford, we drove into New Preston for lunch at Number 9 Main (now the Smithy Café). As we ate our sandwiches at a picnic table, we picked up a real estate booklet, and one house immediately caught our eye. We decided to go see it. It was one of twelve or so houses we looked at throughout Litchfield County, in addition to other towns closer to Manhattan. We considered a mid-century kit house in Sherman and a cottage on a stream in Washington. But once we drove through the Litchfield town green on the way to what would become our home, we fell in love. 

In our first few years here, we were busy renovating our house and spent little time outside of it, except for quick runs to Meraki Kitchen for lunch or Friday night dinners at the bar at The Village (both of which remain two of our favorite spots). Once the dust settled and that first summer came, we really began exploring the area. It was around that time that Architectural Digest published an article about the region, answering a very important and long-debated question between Kevin and me—does Diane von Furstenberg live here? According to AD, she did. Which meant that it was in fact Diane von Furstenberg we saw crossing the street at Arethusa a Mano, and I did nearly hit her with our car. We later saw her hiking at Bee Brook and nearly died of excitement. Litchfield and the surrounding area became officially fabulous in our eyes. 

Whether you call it Litchfield County, Litchfield Hills, or the Northwest Corner, the area is really so much more than any one single community—it’s the combination of all of them that provides a full, rich experience. Each season here has its charms, but fall is really spectacular. Here is my ongoing go-to list for our little corner of the world. A forewarning, I use the word “friend” a lot, but it is a small town and these are our friends :).

Eat & Drink

Being a small town, many establishments close on certain days of the week or for periods throughout the year. Living here has become a juggling act of deciding where to go on what nights or where to eat depending on the season. Reservations are typically required, but a simple ring-up can generally land you a spot at the bar. 

Community Table (New Preston) is excellent—one of our absolute favorites. Like many of the restaurants here, the food is locally sourced and the menu is seasonal, though a few staples remain. The bread is always divine. It is a sourdough right now, but their Parker House rolls will ruin you. The homemade seeded crackers are perfection. Monday night is “burger night,” when most locals meet for dinner. It’s not uncommon to spot a celeb, but even if you don’t, Jo-Ann, the restaurateur, will make you feel like one. Karen, the head bartender, is a ray of sunshine, and her margaritas are epic—especially the spicy ones.

The Owl (New Preston) is the perfect place to meet a group of friends and sit outside. The patio is great in summer and fall when the fire pits are everywhere, otherwise the porch is open all year long. On colder weeknights, you can cozy up at the bar across from the fireplace. The menu is focused and features delicious pizzas, salads, and small bites. It is primarily a wine bar, but has cocktails and craft beers as well. It’s also the only spot in town to celebrate Gay Pride, and their annual event has become an institution. Start your evening here and then meander down the hill to the shops (more on those later).

The Garden Room at the Mayflower Inn (Washington) has one of the best brunches. The beignets are a must, the trout smørrebørd is a real treat, and their Caesar salad is honestly the best I’ve ever had (especially if you’re a Caesar purist and into anchovies). Request a seat by the window so you can enjoy the sun and the view—it feels like you are in another world. On Friday nights, head to their Tap Room and order a martini and a burger at the bar. The space is dark and cozy—it feels like a warm hug. Bonus if you see Candice Bergen dining with her dog at her feet. 

The Pink House (West Cornwall) is the newest addition to the restaurant scene, and the setting couldn’t be more quaint—just a stone’s throw from Cornwall’s iconic covered bridge. Marina, one of the owners, can be seen floating about the room chatting with everyone like they are old friends, and she’ll undoubtedly be wearing something gorgeous. A warning: you’ll want to order several of the arancini appetizers because they are amazing. The “chocolate chocolate chocolate” dessert looks like something a child chef would make—but a brilliant child chef who knows exactly what every adult wants. The “very special fries” are, in fact, very special, and the rest of the menu speaks for itself. You might be familiar with chef Gabe McMackin’s work (The Finch in Clinton Hill), but he has truly outdone himself here. 

On the Litchfield green, Marketplace Tavern has an outdoor terrace where you can watch summer concerts and fireworks while you dine. If you are having a picnic or going to the lake, grab sandwiches from Petraroia Deli. The fried artichoke sandwich is a local favorite, and their BLT is excellent.

The best coffee can be found at Krafted Brew Lab (Bantam). Jason roasts their own specialty beans, and though the Bantam blend is our favorite, there are always new, limited-editions worth trying (look out for the Bali Blend). Their seasonal lattes are signatures, and the rose cardamom chai tea latte is my current go-to. The espresso brownies and salted chocolate chip cookies are weekend staples.

The best quiche can be found at Meraki Kitchen (Litchfield). It is always vegetarian and made with whatever is fresh and abundant. Their porchetta breakfast sandwich is also killer. It’s a popular place for locals, so there’s usually a line on the weekends. Once you meet owners Patti and Martin, you’ll understand why—they’re always in the kitchen, smiling. 

The best ice cream can be found at Aretusa Creamery (Bantam). It is not uncommon to see groups outside with cones as early as 11 AM. The ice cream flavors are simple but delicious. There is usually a seasonal flavor, and their ice cream sandwiches are famous. The first time I had one, it was a Ratatouille moment—I was immediately, poignantly transported back to my childhood. As for the egg nog, I’ve never had the chance to try it because it sells out so fast. 

Stay

Troutbeck is in Amenia, NY but is considered part of our corner. Though we live close, we have made a tradition of spending New Years Eve there with friends and our dogs. When I first met our friend Anthony Champalimaud (before the hotel opened), he described wanting it to feel like the grandchildren had been left an old estate and wanted to make it hip. He also described this much more eloquently, but I dare say he has succeeded. It is a superbly cool, rich, thoughtful and inspiring place. If staying, the Manor rooms are unique and intimate with many original details. You really feel a sense of the history here. The Benton House has been newly redesigned and expanded. Each room has a fireplace and a porch. These are a bit more gracious in scale and best for a long stay. The Barns offer wellness services, classes, and spa appointments. The Tall Barn is serene. In the fall, fire pits along the river are magical. Monday night is pasta night at the restaurant. Throughout the year, Troutbeck hosts cultural events like readings, film viewings, arts classes, and has a rotating art collection. Their holiday market is absolutely worth adding to the calendar. And their sister hotel, Belden House, is opening soon in Litchfield. It is a few steps from the town green and the anticipation is extreme.

Staying at the Mayflower Inn (Washington) is a total dream. The team treats you like royalty from the minute you book. It is very pretty with interiors by Celerie Kemble, but has much of its traditional charm. Because we live in the area, we prefer to hide out and spend most of our time on the property without leaving the spa. Operated by The Well, the spa is to die for. It is serene down to every last detail. You will want to spend an entire day there, and you don’t have to be a guest to do it. The full body scrub is a gift (ask for Chantal). Massages are a must. There is an indoor pool and multiple types of sauna and steam rooms. Also, the restaurant will deliver your lunch to you. And the robes. You will see what I mean.

Lost Fox Inn (Litchfield) just opened and is already becoming quite popular. The restaurant will for sure be a local hangout, but it’s perfect for an autumn lunch or dinner.

The Abner (Litchfield), a Salt Hotel, just opened. It’s in the center of our town green in our historic landmark courthouse. As you could imagine, it was quite the controversy, and expectations were high. I was lucky enough to get a sneak peek before it opened and afterwards I literally ran to Milton Market to gush over it. Kevin O’Shea led the design of the interiors and the result is lovely and incredibly thoughtful. Kevin repurposed the judge’s bench as a check in desk for the restaurant, and many of the original details are showcased throughout. The paneling is killer, but the restored fireplaces in the guest rooms steal the show. Kevin worked with local resident Lori Bookstein, who owns the Manhattan gallery Bookstein Projects, to curate the art collection. Look for gorgeous contemporary paintings by Dave Walsh in the restaurant lounge, a mezzotint at the host desk, Duke Ellington at The Apollo Theater by Romare Beardon, and tapestries by the sculptress Louise Kruger. In addition to a full restaurant, it also has the area’s first rooftop cocktail bar. The views are stunning and you will definitely want spots at the rockers in October (with hot toddy’s), so you can gaze at the foliage. Indoors you might see a few of our Dumais Made lamps and pieces throughout. We designed several originals inspired by the courthouse clocktower.

Shop

Our good friend Martha Fish has the best shop in Litchfield. Milton Market modern-day general store and gallery. It carries bespoke items curated and sometimes designed by Martha in collaboration with local artisans. You will find artwork and gilded pieces by Carol Leskanic, chenille stem sculptures by Greg Domres, textiles by Schuyler Samperton, and paper florals by The Green Vase. Martha hosts intimate classes in the shop with local artisans where they teach you their craft. Spots for these sell out quickly. And, perhaps most importantly, the hand-painted monogrammed steel canvas totes are brilliant and make the best gifts for others or yourself. We’re working together on a special lamp that will be exclusive to this shop.

Our friend Paul described the shops in New Preston perfectly. He said, “Each is the quintessence of itself.” And he is right. Plain Goods is in the historic Harry O Erickson Pavilion Hall. Michael DePerno and Andrew Fry undertook an extensive and thoughtful restoration, and their building has become an icon in New Preston. And then you go inside. It is described as a lifestyle shop, and it sure is. Their point of view is perfectly executed within. It is a mix of antiques, housewares, clothing, and artwork selected and displayed with effortless precision. The clothing is beautiful with brands like Fujito, Margaret Howell, A Vontade, and Orslow, Vintage pieces, accessories and treasures abound. Privet House (New Preston) smells amazing with home and apothecary goods for sale. Richard Lambertson and Suzanne Cassano continue to curate a lovely trove of home goods, antiques and curiosities. Upstairs there is one space dedicated to a designer installation. It’s currently Ostafin Design, but it changes seasonally and is always a welcome surprise. The linens are superb, and you will want every gorgeous type of brush or broom. I always shoot right for the book corner upstairs. The “library” exclusively features vintage books, mostly art and autobiography with occasional gems like Truman Capote’s complete works, which I managed to grab a few of.

At Pergola (New Preston), home meets nature through a Japanese lens. David and Peter Whitman should start a museum of Japanese ceramics because their knowledge and eye for it is impeccable. During the pandemic they sold the most beautiful face masks made from vintage Japanese kimono textiles – so beautiful I still have them. 

George Home CT (Washington Depot) features a curated mix of mid-century modern, antique, and contemporary furniture and objects. Bruce Glickman is a darling and you will want to keep shopping just to hang out with him.

Housatonic Trading Co. (Bantam) is our neighbor and owned by our friend Robert Graham. It is a home and design shop with handpicked antiques, vintage, and new pieces of furniture and accessories and even jewelry. Follow them on Instagram because Rob posts new arrivals frequently and they sell out before you can drive there. You never have to go to an estate sale, because Rob brings it all to his shop. Rob’s wife, Rebecca Godson, has a corner where she sells handmade jewelry alongside antique and vintage pieces she collects. She will also create custom jewelry for you, which is so much fun.

Explore

Hiking in our corner is a thing. It is not my thing, but there are some places you will want to explore. Topsmead State Forest (Litchfield) is the former summer estate of Miss Edith Morton Chase. It is perfectly preserved and a delight in any season. It is open to the public during daylight hours. Bring the dog for a hike or a picnic to watch the sunset. Occasionally the manor is open for public tours and when it is, it is a must. In the fall, the fields are golden with an autumnal technicolor backdrop.It will take your breath away. 

The Boardwalk in White Memorial (Litchfield) is great for a run or a long walk. You will be shocked you are in rural Connecticut and think you are in the dunes on Cape Cod. To add to the illusion, head to West Shore Seafood after on Bantam Lake, and have a lobster roll.

Lake Waramaug (New Preston) is mostly private, but there is a state park entrance at the northwest end where you can park and go to the beach. You can bring your own kayak, canoe or paddle board, but can also rent them there in the summer. If you row or paddle out to the center, you get a 360-degree view of heaven. Bee Brook (Washington CT) – The hike is easy except in the winter. The two bridges are worth seeing and, if you make it there in the fall, you will become a lifetime leaf peeper. And you might run into DVF, and then nothing else matters.