One of the questions I get asked most often is, “How did you end up in Litchfield County?”.
As we approach our two-year anniversary of leaving the city, it feels like the right time to finally answer that question.
While I’ve always been somewhat protective of exactly where we live, many of you have pieced together that we’ve settled in Litchfield County, Connecticut. Over the last two years, countless messages from people we’ve met in the community, everyone asks the same thing: What brought you there?
The truth is, it wasn’t family. It wasn’t work. It was a feeling.
Growing up in Northern California, I have always carried a deep nostalgia for life lived closer to nature. The kind of childhood that revolves around hiking trails, river swims, farm stands, horseback riding, wildflower fields, winding country roads, and afternoons spent outdoors until the sun disappears behind the hills. Somewhere along the way, city life became home, but that longing for open spaces never really left me.
Years ago, Freddie and I escaped for a weekend at The Mayflower Inn & Spa. What was meant to be a simple getaway ended up changing the course of our lives. That trip introduced us to Litchfield County, a collection of charming New England towns tucked into the northwestern corner of Connecticut, nestled between rolling farmland, forest preserves, and the foothills of the Berkshire Mountains. It felt worlds away from New York, yet somehow close enough to remain connected. What immediately drew us in was the way life felt here.
There are antique trails that stretch from town to town, family-owned farms operating much as they have for generations, beautiful country inns, vineyards, winding back roads, hidden lakes, historic homes, and a community filled with artists, makers, chefs, gardeners, designers, and entrepreneurs who have intentionally chosen a slower pace of life. And then there are the hotels.
For such a small corner of New England, Litchfield County is home to an extraordinary collection of destinations. The Mayflower, Winvian Farm, Belden House, Troutbeck, The Abner, Lost Fox Inn, and several others continue to attract travelers from around the world. I think that says something about the magic of this place.
Writing this guide has honestly felt a little overwhelming. Not because there aren’t enough places to include, but because there are too many. Over the last two years, we’ve built friendships with so many local business owners, artisans, farmers, chefs, and families who make this community what it is. We believe deeply in supporting small businesses and local makers, and I know many of you will use this guide when planning your own visits. I could easily break each of these categories into far deeper lists and perhaps, I will in the future as I continue to explore and discover.
So while I am certain I’ve forgotten a few favorites, this guide is my love letter to the county that welcomed our family with open arms.
Without further ado, here is my 2026 Litchfield County Guide.
Restaurants
One of New England’s few prestigious Relais & Châteaux properties, Maggie’s Tavern at Winvian Farms offers an elevated farm-to-table dining experience in an extraordinary setting. Seasonal ingredients, impeccable hospitality, and the charm of the surrounding estate make every meal feel like a special occasion.
The setting for my 40th birthday celebration and one of my favorite destinations in the county. Beautifully restored and exquisitely designed, the inn is layered with antiques, collected details, and old-world charm. Whether for dinner, drinks, or a special event, it feels effortlessly elegant and always worth a visit.
A longtime local favorite that has quietly become one of the county’s most celebrated dining destinations. The farm-driven menu, intimate setting, and consistently exceptional execution make it a place we return to again and again. After a recent dinner, Freddie summed it up best: “It’s not just a good restaurant for this area. It’s one of the best restaurants I’ve ever eaten at.”
For sunset cocktails and sweeping views of downtown Litchfield and its iconic 18th century architecture and surrounding hills, this is hard to beat!
Located in the heart of downtown Litchfield, Belden House offers a refined yet approachable dining experience centered around seasonal New England ingredients and elevated American cuisine. Whether you’re stopping in for cocktails on the terrace, a leisurely dinner, or pairing your meal with an afternoon at the spa, it’s the perfect place to settle in and make an evening of it.
One of Connecticut’s most celebrated dining destinations, Arethusa al Tavolo is known for its sophisticated farm-to-table cuisine rooted in the exceptional dairy and agricultural products from the nearby Arethusa Farm. Thoughtfully prepared seasonal dishes, impeccable ingredients, and understated elegance make every meal here memorable.
A longtime local favorite known for its elevated American fare, warm hospitality, and charming historic setting. Cozy, welcoming, and consistently delicious, it’s the kind of place you’ll find yourself returning to again and again.
A casual local favorite serving some of the best authentic Mexican food in the county. You can find us here every Taco Tuesday. From tacos and tortas to fresh-made salsas and traditional specialties, it’s unfussy, flavorful, and always hits the spot.
One of the most beautiful dining settings in Litchfield County. Nestled within the grounds of The Mayflower Auberge Resort, the restaurant overlooks sprawling English gardens and rolling manicured lawns with fire pits made for gathering. Wandering through the gardens before or after a meal is part of the experience.
Set inside a historic 18th-century tavern, GW Tavern is a longtime Washington favorite known for its classic New England charm, welcoming atmosphere, and elevated comfort food. Whether you’re stopping in for a burger by the fireplace or a leisurely dinner after a day of exploring, it captures the timeless spirit of Litchfield County.
Located in the heart of Kent, Swyft is a charming all-day café and market that’s become a favorite stop for coffee, breakfast, and casual lunches. With its bright interiors, thoughtful provisions, and menu of fresh, seasonal offerings, it’s the perfect place to fuel up before a day of antiquing, hiking, or exploring the surrounding towns.
A charming countryside pub that feels straight out of the Cotswolds. Set along a small river with room for kids to explore, it’s as inviting outdoors as it is inside, where exposed beams, crackling fireplaces, and classic pub fare make it the perfect spot to unwind after a day in the countryside.
My go-to lunch destination for beautifully prepared grab-and-go meals, fresh salads, sandwiches, and seasonal specialties. Perfect for stocking up before a picnic by the lake, a day of antiquing, or simply enjoying a leisurely afternoon.
Our family’s go-to pizza spot and a local favorite for good reason. Known for its wood-fired pizzas, laid-back atmosphere, and community feel, it’s the kind of place where everyone ends up gathering after a day in town. Casual, welcoming, and consistently delicious.
A classic small-town deli serving up hearty sandwiches, homemade salads, and all the essentials for a day of exploring. Whether you’re grabbing provisions for a hike, a picnic, or lunch on the go, it’s one of those local institutions that never disappoints.
Family Activities / Seasonal Events
The Goshen Fair – Late August
Litchfield Wellness Festival – June
Fall Foliage Season – October
Fenimore Lane Design Summit – June
Trade Secrets – May
Ticking Tent – June
Thorncrest Farm – year round
Part working dairy farm, part chocolate lover’s dream. Families can visit the cows, learn about farm life, and stop into the farm shop for their famous handcrafted chocolates made with fresh cream from the herd. It’s one of those quintessential Litchfield County experiences that children never forget.
White Memorial Conservation Center Museum – year round
The museum at White Memorial is one of our favorite activities with the girls. Designed to spark curiosity about the natural world, it features interactive exhibits, local wildlife displays, and hands-on learning opportunities that make nature feel exciting and accessible for children. It’s educational without feeling like a lesson, which is exactly why kids love it. There are also miles of trails to hike!
Averill Farm – Fall
A family tradition for us every fall. We visit each year with the girls for apple picking, warm cider donuts, and some of the most beautiful views in all of Litchfield County.
Markets
Lovingly named “The Smoothie Grocery Store” my Lucy, it’s a beloved natural foods market offering organic produce, specialty groceries, prepared foods, fresh juices, and one of the best selections of local products in the area.
Bantam Market, Bantam
Our charming neighborhood market stocked with gourmet provisions, fresh sandwiches, prepared foods, and everyday essentials.
The Smithy Market, New Preston
Part café, part market, and part gathering place, offering seasonal provisions, fresh flowers, pantry staples, prepared foods, and beautifully curated local goods.
Warren General Store, Warren
A classic small-town general store serving breakfast, lunch, coffee, baked goods, pantry staples, and everyday necessities with plenty of local charm.
The Dutch Epicure Shop, Litchfield
A beloved local bakery and specialty food shop known for its exceptional pastries, cakes, cookies, and European-inspired baked goods.
The Bakehouse, Litchfield
A destination for artisan breads, pastries, sandwiches, and expertly crafted coffee, all made with a focus on quality ingredients and traditional techniques.
Roadside Favorites & Farm Stands
A family-run farm known for its seasonal produce, flowers, and picturesque countryside setting.
Litchfield Candy Co., Litchfield
A charming sweet shop offering handcrafted chocolates, nostalgic candies, and seasonal treats for all ages.
Nick’s Country Kitchen & Bagels, Bantam
A local favorite for freshly baked bagels, hearty breakfasts, and casual morning gatherings.
Wise Old Dog Organic Wines, Morris
A thoughtfully curated wine shop specializing in organic, biodynamic, and small-production wines from around the world.
Ox Hollow Farm Stand, Washington
A seasonal roadside stand offering fresh produce, flowers, eggs, and locally sourced goods.
West Shore Seafood, Bantam
A hidden gem for fresh seafood, prepared specialties, and classic New England favorites.
Bantam Bread Company, Bantam
A beloved artisan bakery known for handcrafted breads, pastries, sandwiches, and excellent coffee.
Blue Gate Bakery, Warren
A charming bakery and antique store serving homemade pastries, breads, cakes, and comforting breakfast and lunch offerings.
Krafted Brew Lab, Litchfield
A modern coffee destination known for expertly crafted espresso drinks, specialty coffee, and a welcoming atmosphere. Always find me here on my laptop when I need to get some uninterrupted writing time done.
Litchfield Distillery, Litchfield
An award-winning craft distillery producing small-batch bourbon, gin, vodka, and ready-to-drink cocktails inspired by New England traditions.
Antiques & Decorative Arts
A beautifully curated mix of French and Italian antiques and fine, handmade linens from Sicily.
George Home, Washington
One of my favorite places to browse for interiors inspiration.
Milton Market, Litchfield
An ever-changing collection of vintage finds, antiques, and local makers. Also, fun fact, you can find Cucina Cipoletti there!
Eleish Van Breems Home, New Preston
A thoughtfully curated destination for Swedish antiques, timeless furnishings, and beautiful home décor.
RT Facts, Kent
An institution for anyone who loves old New England furniture and collectibles.
Farmhouse Antiques, Woodbury
A treasure trove of English and American antiques, garden pieces, and collected finds for the home.
Marché, Falls Village
A beautifully curated destination blending European antiques, home décor, and unique vintage finds.
100 Main, Falls Village
An eclectic mix of antiques, art, and decorative objects housed in a charming historic building owned by the iconic Bunny Williams and also where you can find Cucina Cipoletti.
Home & Lifestyle
A design destination for anyone who loves interiors, fashion, entertaining, and collected living.
J. Seitz & Co., New Preston
A beloved lifestyle shop filled with fashion, books, home goods, gifts, and beautiful everyday essentials.
HTC Home, Bantam
A thoughtfully curated collection of furnishings, antiques, lighting, and home accessories.
Hayseed on The Green, Litchfield
A charming shop known for its mix of home décor, garden-inspired finds, gifts, and seasonal treasures.
Fashion
Oliphant, Litchfield
Beautifully curated fashion and home pieces with a distinctly European sensibility.
Westerlind, Litchfield
A thoughtfully edited collection of outdoor apparel and lifestyle goods.
Pinnacle, Washington Depot
All the best ready to wear brands under one roof and my go-to destination for everything these days!
Bookshops
House of Books, Kent
A quintessential independent bookstore and one of Kent’s most beloved institutions, filled with thoughtfully curated books, gifts, and stationery.
Hickory Stick Bookshop, Washington Depot
A longtime local favorite offering an excellent selection of books, author events, and a warm small-town bookstore experience.
Hotels & Resorts
A destination in itself. The whimsical cottages, exceptional food, and sprawling grounds make it one of the most unique stays in New England.
Boutique luxury meets wellness retreat. A beautiful place for a weekend escape.
The property that started it all for us. Timeless, romantic, and effortlessly elegant.
Charming, intimate, and perfectly situated for exploring the surrounding towns.
Just over the New York border, but absolutely worth mentioning. One of the most beautiful properties in the region technically NOT in Litchfield county but worth mentioning.
Hikes / Nature Walks
Laurel Ridge Farm Daffodil Walk
Health & Wellness
A beautiful studio offering yoga, movement, and community. Catch Rebecca’s class!
One of my favorite wellness destinations in the county.
Excellent instruction in a welcoming environment.
A favorite among cyclists and outdoor enthusiasts exploring the county’s scenic roads.
A destination for weekend women’s retreats what are equal parts mind and body nourishing.
World-class wellness programming in one of the most beautiful spa settings in the Northeast.
The thing I love most about Litchfield County isn’t any one restaurant, hotel, or antique shop. It’s that life feels a little slower here. People are kind and neighborly in the old fashioned way.
You find yourself lingering over coffee and always running into someone you know. Stopping at farm stands. Learning the names of local business owners. Taking the long route home because the scenery is simply too beautiful not to.
In a world that increasingly feels rushed, Litchfield County reminds me that there is still great joy to be found in simple pleasures.
And perhaps that’s what brought us here after all.
