Long a favorite country getaway for New York City finance professionals, Connecticut’s Litchfield County—home to the picturesque towns of New Preston, Cornwall, Kent, New Milford, Litchfield, Bantam, and Washington—has in recent years become a go-to retreat for creatives and food lovers alike. “There’s something for everyone: art galleries, outdoor activities, shopping, great food,” says Cheri Bowen, a talent manager at The Society Management, who settled in the area with her family years ago. “With its covered bridges, forests, and rivers, the scenery is gorgeous. In fact, every season challenges the next for which is more beautiful.” Just in time for leaf-peeping season, when the fall foliage in Connecticut’s northwest corner is a sight to behold, here is Vogue’s guide to the area. Below, a look at where to stay, shop, and eat should you decide to make your way to Litchfield, Connecticut for an idyllic weekend away. Just be warned that there is one tiny downside: “The drive back home when you realize there are five whole days to wait until you get to come back again,” laughs Bowen. Photo: Courtesy of Auberge Collection Where to Stay in Litchfield, Connecticut No trip to Litchfield is complete without a stay at the bucolic Mayflower Inn & Spa, Auberge Collection. This pastoral hideaway has long drawn the stylish crowd up north—and it’s easy to see why: The property, which consists of a resplendent English country house and three standalone cottages set on 58 serene acres, feels like something out of a fairy tale. Each room features charming details (four-poster beds, lavish soaking tubs, Edwardian wallpaper) with views of the grounds—including the property’s magical Shakespearean walking garden. Enjoy a meal by chef Luke Dowdy, an alum of the Thomas Keller Group and Jean-Georges, or indulge in a holistic wellness treatment at their on-site oasis, The Retreat. Be sure to check out the ever-changing roster of activities, including country excursions outfitted by outerwear company Barbour and parlor games featuring Checkers, Tic Tac Toe, and Connect 4 designed by Edie Parker. Photo: Courtesy of Auberge Collection For a slightly more rustic experience, book the Treehouse at Winvian Farm in Morris. The wood-paneled cottage set 35 feet above the ground is way more grown-up than you might initially expect: It has a king-size bedroom, wood-burning fireplace, steam shower, full bar, and a jacuzzi. Guests of the treehouse—or any of the property’s other cozy cottages—also have access to Winvian’s other amenities, including yoga classes and bikes to explore the 113-acre resort’s wooded trails and organic gardens. The Cottage room Photo: Courtesy of The Litchfield Inn If you consider yourself something of a modern traditionalist, there’s also The Litchfield Inn. Housed in a classic 18th-century colonial estate set amid 10 acres of rolling hills and forests, it features 32 guest rooms and an unfussy New England aesthetic. Our favorite room? The cottage. With its white shiplap walls, four-poster king-sized oak bed, and cute rattan wall sconces, it manages to feel both cozy and minimalist at once. New to the scene, as of 2025, is Belden House and Mews, a luxury boutique hotel from the team behind the Hudson Valley’s esteemed Troutbeck Hotel. “An air of relaxation extends to every facet of the Belden House & Mews experience, from the bathroom’s stock of Wildsmith products to the lush Frette linens on the beds and the house’s idyllic front porch, perfect for a slow morning over coffee,” writes Vogue’s own Hannah Jackson. But the highlight? It was “undoubtedly the spa, where my esthetician, Christina, gave me a transcendent facial that left me floating between wake and sleep, and my skin feeling refreshed.” And for those who would rather have their own space to use as a home base, an Airbnb is your best bet. This Litchfields Hills cottage is on the border of Washington and Bantam, with five acres of outdoor space to explore and quaint interiors that include a lemon-yellow kiThe kitchen. Photo: Read McKendree
Where to Shop
Historic New Preston has become a serious shopping destination, thanks in part to the cult-favorite boutique Plain Goods. Tucked inside a tiny whitewashed cottage just off the easy-to-miss main street, the shop celebrates life’s simple pleasures: home furnishings, clothing, accessories, and beauty products in a pared-down palette of natural textures and neutral tones. If that sounds boring, it’s anything but—everything is luxurious and tactile, from handmade cross-body pouches in burnished caramel leather to ribbed mock neck sweaters made from 100% cashmere. Alongside pieces from the in-house brand, you’ll also find a carefully curated mix of vintage items and antique treasures. Think sleek stoneware containers, French linens in faded plaids, opaline glass lamps, and primitive wood cupboards, as well as pre-owned Etienne Aigner and Coach bags. In short, it’s the kind of store that will make you rethink your entire aesthetic—and at the very least, tempt you to buy everything in sight. Photo: Courtesy of Plain Goods
For those who prefer something a little more extravagant, head next door to J. Seitz & Company, a two-story lifestyle emporium founded by a former magazine editor and filled with all kinds of eclectic objects to covet: slip-covered furniture, cashmere sweaters, and artisan-made apothecary gifts. There’s so much to see among the artfully arranged displays that it’s easy to lose track of time. But that’s fine: the sound of rushing water from the town’s 40-foot waterfall, located right behind the store, creates a soothing, unhurried atmosphere.
In Sharon, check out the decor and curio shop Dugazon, opened in 2025 by former fashion editor and magazine executive Matthew Marden and his husband, Bobby Graham. “Housed in a charming storybook clapboard cottage (complete with wraparound porch) along Main Street in Sharon, the space features an eclectic curation of delightful bits and bobs: John Derian painted dishes, Charvet Editions linens, small-batch pottery from local makers, antique silverware and candlesticks, glossy coffee table books, woven baskets, and gourmet food provisions, to name just a few,” says Vogue’s Max Berlinger. “It has the feel of both an old-timey general store and the most polished urban boutique.”
In Washington Depot, there’s Pinnacle, a boutique from longtime friends Betsy Goldin and Caroline Klein that sells clothes by Alex Mill, TWP, Ulla Johnson, and more. In Kent, you can stroll through the art galleries, pick up your weekend read at the House of Books, or browse sustainable clothing and home decor at Rentrayage, the flagship of former CFDA finalist designer Erin Beatty’s brand, known for giving new life to vintage fabrics, old clothes, and deadstock. For Issey Miyake fans, check out Workshop in Litchfield, which has a nice selection.
And of course, a country shopping trip is never complete without a day spent hopping between antique markets. Luckily, Litchfield has plenty to satisfy the urge. In New Preston, visit Dawn Hill Antiques for neutral, Swedish-inspired decor and River Song Country Antiques for quaint country classics. In Woodbury, Farmhouse Antiques & Design offers a down-home selection, while Mill House Antiques & Gardens features more upscale furnishings. Elephant’s Trunk Flea Market in New Milford is the largest flea market in New England, making it a must-visit any Sunday from April through December, weather permitting. In New Preston, D.K. Schulman Design is a gift shop and stationery store specializing in personalized invitations.
Where to Eat
In an area filled with rolling hills, apple orchards, and sprawling farms, it’s no surprise that many local restaurants focus on farm-to-table fare. What may be surprising is the range of atmospheres in which it’s served. At the White Horse Country Pub and Restaurant in Marbledale, the decor leans toward antique British (cream walls, dark wood furniture, equine art),The menu features American classics with a modern twist, most of them made with ingredients grown in the pub’s fields at Back Forty farm. On warmer days, grab a seat on the pub’s patio—the perfect spot to linger over a burger and a Bloody Mary while watching the river below. Photo: Courtesy of Arethusa Farm Dairy
In Bantam, Arethusa Al Tavolo also sources ingredients from its own farm, though here they come from the restaurant’s namesake dairy farm right next door—and the atmosphere is decidedly more elegant. Along with super-fresh butters, cheeses, and yogurts, the ever-changing seasonal menu by executive chef Dan Magill offers refined dishes like Atlantic skate with green onion risotto and hen-of-the-woods mushrooms, and heritage pork tenderloin wrapped around caraflex and leeks. (Be sure to stop by the Arethusa Farm Dairy store before or after your meal—it’s the perfect place to stock up on aged cheeses, fresh-turned butter, and the most decadent ice cream, and it’s housed in a charming red brick building that was once the Bantam Firehouse.) Plus, there’s Bantam Bread for all your artisanal bread needs.
Just down the road is another hidden gem: West Shore Seafood. The eatery is charming in its simplicity—just a few picnic tables under an airy tent with space to play cornhole out back—but the kitchen serves some of the freshest, best-prepared seafood around. The menu ranges from classics like fried calamari and a truly exceptional Connecticut lobster roll to more elevated options like delicate sesame-seared tuna and pan-seared salmon salad. It all pairs perfectly with the house-made lemonade or a crisp white from the full-service bar inside. Photo: Courtesy of Community Table
At Community Table, executive chef Marcell Davidsen brings an understated Nordic sensibility to the area’s locavore tendencies. The restaurant, housed deceptively in an old white colonial house on a country road between Washington Depot and New Preston, has an interior as modern and chic as the beautifully plated dishes, with a pared-down dining room featuring warm paneled walls, peaked ceilings accented by floral wallpaper, and dark spindle chairs. The menu changes weekly, but recent mouth-watering options—mostly plant-based—include seared local mushrooms with garlic-leek risotto and green romesco, coffee and five-spice roasted carrots with herbed labneh dressing, and house-made six-grain sourdough bread with maple butter.
Litchfield is its own escape, but you’d be forgiven for thinking you’d landed in a quaint European city after visiting The Owl. The airy New Preston wine bar, with its twinkle-light patio perched on a hill, is the ideal spot for an al fresco aperitivo. Order the homemade meatballs, polenta with sautéed mushrooms and mascarpone, and a pepperoni-and-hot-honey pizza, along with any of the interesting wines or local craft beers on the tidy beverage list.
In West Cornwall, you can’t go wrong with dinner at The Pink House (or pastries in the morning at their new coffee service, Pink House AM). Set in a charming—you guessed it!—pink house, the buzzy bistro is the first project from stylist-turned-restaurateur Marina Muñoz and business partner David Ellen, a longtime Cornwall resident. “The food was delicious,” Vogue head of editorial content Chloe Malle wrote of a snowstorm-eve dinner at The Pink House earlier this year. “I loved the three-day chicken soup and za’atar carrots—and I loved the works by local artists decorating the space, like Laurie Simmons’s photographs of desserts.”
Frequently Asked Questions
FAQs Why Litchfield County Connecticut Is the Perfect Fall Weekend Getaway
1 Where is Litchfield County Connecticut
Its in the northwest corner of Connecticut bordering New York and Massachusettsabout two hours from New York City and Boston
2 Why is fall the best time to visit
The foliage The countys hills and covered bridges turn brilliant shades of red orange and gold usually peaking from late September through late October
3 When exactly does peak foliage happen
Typically early to midOctober It varies year to year so check Connecticuts fall foliage report before you book
4 What is Litchfield County known for
Rolling hills scenic country roads small New England towns covered bridges farms wineries and historic inns
5 What are the mustsee towns
Litchfield Kent Washington New Milford and Salisbury are all popular and charming
6 Do I need a car
Yes Attractions are spread out and public transit is limited A car is essential
7 What are the top things to do in fall
Leafpeeping drives apple picking hiking visiting wineries and farms browsing antique shops and exploring covered bridges
8 Whats the best scenic drive
Route 7 along the Housatonic River and Route 202 through Litchfield are favorites The drive up to Mohawk Mountain offers great views
9 Where can I go hiking
Try Mohawk Mountain State Park Kent Falls State Park or the Appalachian Trail sections near Salisbury
10 Is Kent Falls worth visiting
Absolutely Its a beautiful waterfall with a short easy trailgreat for all ages
11 What about apple picking and farms
The county has many orchards and farm stands Places like Ellsworth Hill Orchard and Averill Farm are local staples
12 Are there wineries nearby
Yes Sunset Meadow Vineyards and Hopkins Vineyard are popular spots for tastings with fall views
13 Where should I stay
Options range from historic inns like the Mayflower Inn Spa to cozy BBs country motels and Airbnb rentals
14 How far in advance should I book
Book two to three months ahead for fall