The Best Inns Near Fairfield County


The Best Inns In and Around Fairfield County


Photo credit: Courtesy of Tavern at GrayBarns

194 Perry Ave., Norwalk

Travelers are gravitating toward historical destinations. It’s as if they want a deeper connection to American culture as their business and social networks become more global,” says Nicole Glazer of Glazer Group, the family-owned company that has reimagined a corner of Norwalk on the banks of the Silvermine River. This address was once a stagecoach stop, a textile factory, a speakeasy during Prohibition and, more recently, the Silvermine Tavern. In 2017, the nineteenth-century structure was reopened as The Inn at GrayBarns, a rustic-chic destination with dashing good looks and earthy charm.

There’s plenty of reclaimed wood, rough stone and butter smooth leather in the six guest rooms and tavern/restaurant. GrayBarns is on the radar of Manhattanites who have done the B&B scene in the Hudson Valley, but it also lures locals who want to leave their own homes to unplug. “We get a lot of couples who want a night away,” says Glazer. “There’s a real sense of calm here. We’ve also hosted groups of locals, including a half dozen women who were here to celebrate a friend’s fortieth birthday.”

What are the features that locals like most? The rooms, for starters. Each suite is a “king,” and sized at about 900 square feet—ample space for amenities such as fireplaces, lounging areas and terraces with river views. And to pamper guests in rustic fashion, there are luxe textiles like cashmere throws, upholstered beds and velvet-covered chairs. As for the rotary phone in each room, “It’s there to provide some digital detox,” says Glazer. “We want guests to really unwind. That’s why the soaking tub is the centerpiece of each bathroom.” The rooms are so inviting at GrayBarns, some people find it hard to leave them, particularly since you can order in special services such as massages and mani/pedis, provided by To And From salon in Darien.

If you can muster up the resolve to lift your head from that mohair pillow, there are bikes (from NYC-based Priority) for guests, who can pedal along the quiet streets to take in the views and historical homes, and rediscover area icons like the Glass House (about three miles away) and Silvermine Arts Center. Afterward, head to the Tavern at GrayBarns, where locally sourced, elevated comfort food prepared by Executive Chef Ben Freemole is served in a dining room framed by dramatic wood beams and lit by a huge stone fireplace. Even if you’ve dined here before, GrayBarns may have a few surprises for you. A Sunday brunch was recently added to the menu, and a pop-up bakery featuring the inn’s own baguettes and breads sets up in the barn on Friday and Saturday mornings. “Having grown up in this area, I felt there were very few options for those who wanted to spend the night in a great inn,” says Glazer. “We’re trying to offer something with real authenticity, a family-run establishment that offers a different level of detail.”

Home-style touches in each guest room include a Nest thermostat, Nespresso machine, 49-inch TV and complimentary WiFi.

Stroll by the kitchen garden, where the chef will be picking greens for your dinner and have a post-dinner drink in the small library off the dining room.

“The Addison room is my favorite,” says Glazer. “It has a beautiful original fireplace and French doors open to a private patio with river views. It has a sense of drama with high ceilings and chandeliers. My boyfriend, however, likes room five because you can see the TV from the bed.”


954 Old Post Rd., Bedford, NY

The drive to Bedford is a snap. Just cross the state line onto country roads lined with stone walls, padlocked gates and trees that loom like sentries over the weekend homes of hedge fund managers who relish the moment they’ll arrive on Friday evening to kick off their wingtips and shut out the city. But urban commuters aren’t the only people who experience that “aha” moment in Bedford. Fairfield County residents travel here, too, specifically to the Bedford Post Inn, if only to feel they’re a million miles away from it all. Yet if the nanny calls in the middle of the night with news that one of the kids is sick, Mom and Dad can hop in the Range Rover and hightail it home in under a half hour.

This is a cozy, eight-room luxury inn set on fourteen acres with lush, mature landscaping. It’s also one of the boutique properties in the Relais & Chateaux global portfolio, which means it’s meticuloulsy maintained and boasts white-glove service. It has celebrity appeal, too, as co-owner Richard Gere occasionally stops by to dine at one of two restaurants on site. Pricey? Absolutely. A weekend here isn’t cheap, but in Bedford, money really can buy happiness.

“It’s a great getaway in any season,” says Lisa Rotondi, the inn’s manager, who believes there’s no better place to get snowed in by the fireplace in one of the guest rooms (and the outdoor firepit is the perfect place to snuggle up and make s’mores). “In warm weather you can spend a lot of time outside. The property is filled with hydrangeas and the walking trails are lovely,” she says. Guests with more ambitious excercise goals can hike in nearby Ward Pound Ridge Reservation; others can explore the Wolf Conservation Center in South Salem. For retail therapy, get a fix in the town of Bedford or nearby Katonah and Pound Ridge.

“There’s a lot to do off-site, but some guests like to stay on the property,” she says. They’ll schedule an in-room massage and facial, and then head over to the Yoga Loft, where multiple classes for all experience levels are scheduled each day.

And then there’s the food. Like all Relais & Chateaux properties, this one offers gourmet dining. Casual meals are at The Barn—a whitewashed outbuilding with just-right rustic accents—where there’s a Sunday brunch and daily dining on the outdoor patio with a woodburning grill so guests can watch the chef in action. With live music and string lights hung beneath a wisteria-covered pergola, it’s a lovely place on a warm evening. The Farmhouse is more formal, although still relatively casual. Until recently, this was the location of Campagna, but this summer a new restaurant opened, offering cuisine that, Rotondi says is “American based with a French influence.”

“Most guests like room seven because it’s the largest,” says Rotondi, “but my favorite is room two. It’s a California king with a terrace that’s more private than the others, and a reading nook with great lighting.”

Each room has an oversized bathroom with claw-foot tub and plenty of cool marble.

“I often encourage guests to go down to Guard Hill Road to look at the beautiful estates and catch a glimpse of peacocks crossing the road,” says Rotondi. “A resident raises the birds and lets them run wild through town.”


420 Field Point Rd., Greenwich

While this 1799 farmhouse on two-plus manicured acres in the Belle Haven section of Greenwich is intimate by virtue of its size with seventeen rooms, it is not your traditional inn. “We are a luxury boutique hotel that is full-service, with staff on hand twenty-four hours a day and a French restaurant rated four stars by the New York Times,” says co-owner Theresa Carroll. “It’s a real getaway, a place that feels more like a little piece of Europe than a corner of New England.”

What makes it that way? The caliber of the smart service, for starters. When you roll up the driveway at this Relais & Chateaux property, a person will most likely step outside to greet you and politely shoulder your bag, even if it’s weighed down by one too many pairs of shoes. Once you’re through the door of the Victorian Italianate manor, you get the sense you’re in a space that’s evolved over time, rather than been made over to follow a trend. “I’m a designer and I change up the rooms all the time,” says Carroll. “I move things around, paint, swap out furnishings and French linens. I love a bit of change. It’s fun. And I never want a guest to turn a corner and see a blank wall. I am not a fan of minimalism. I’m of the ‘more is better’ school.”

In the public spaces, you may see a mirror framed with porcupine quills hanging over a table covered with garden mosses, ferns and terrariums. Over in another corner, forged iron and bronze sculptures could share space with baroque furnishings and accessories by Bunny Williams. Here, old meets new with panache.

Despite the charms of the guest rooms (which are located in the main building and carriage house), many people who come to the Homestead aren’t aware you can spend the night. That’s because they get so disctracted by the food.

The French cuisine prepared by a world-class chef—Thomas Henkelmann—is consistently rated sublime by returning guests and food critics alike, who also applaud the country-elegant atmosphere in the dining room with exposed beam ceilings and fireplace, and impeccable service. White linen, fine china and gleaming silverware are the backdrop for Henkelmann’s culinary artistry—think sautéed sweetbreads with Perigord black truffle sauce, seared Hudson Valley duck foie gras with macaroni and cheese and carmelized Granny Smith apples, and Grenadin of veal with a Maine Lobsterrisotto, parmesan lace, watercress and a port wine sauce.

When guests are not eating during their stay, what do they like to do? “Some go to the Avenue, others hike at the Audubon Center, or play a round of golf,” says Carroll. “But for the most part, people who come here are simply looking to do their own thing.”

It’s on the terrace, which offers nice views of the property and overlooks a pretty coleus garden.

The best way to start your day, says Carroll, is with a breakfast of eggs Benedict at the restaurant. “It’s made with the best hollandaise sauce you have ever tasted in your life.”

The bar at Homestead boasts a top selection of spirits, from brandy to single malt scotch. But more appealing is the bartender, Astley Atkins, who has his own fan club. Why is he so loved? “I can’t articulate it,” says Carroll. “It’s hard to explain what makes someone cool.”


260 Compo Rd. South, Westport

It’s perhaps best-known as a busy venue for weddings and bar/bat mitzvahs. And during the week, the location draws its share of business travelers who are willing to sacrifice loyalty points at a favorite hotel chain for the chance to stay in a place that feels more like a destination, with soothing shoreline views and a long, curving drive that puts the nearest highway far out of earshot. But The Inn at Longshore also appeals to locals craving a New England-style beach escape in any season. A number of these guests are repeat customers, too, including some who have been checking in for more than twenty years. Many choose Longshore for special celebrations. One couple recently booked a stay for their twentieth wedding anniversary. They arrived in the afternoon, making sure to carve out time for a walk from the property over to Compo Beach before heading back inside for dinner at the on-site restaurant; then they were off to the Westport Country Playhouse for a show.

The Inn was built in the late 1800s as a private estate, so it has quirks: There’s no elevator, for instance, just walk-up access to floors above the main level; and in the summer, guests are cooled by air-conditioning units installed in the windows. These things don’t seem to bother fans of Longshore, though, who are quick to praise the twelve guest rooms (particularly the suites as they include comfortable sitting areas), the garden and water views, and access to resort-style amenities, including tennis courts, pool and an eighteen-hole golf course built in the mid- 1920s by architect Orrin E. Smith and later renovated by John Harvey. Water sports rentals (think sailboats) are nearby for summer guests; winter visitors can go ice skating. Of course, repeat customers will tell you to choose your dates carefully; if you want a quiet, relaxing stay, book when there’s no wedding on the inn’s schedule.

When you’re hungry, dig into the American cuisine at The Pearl, where the menu typically offers extensive raw-bar options, homemade pastas and steaks. The dining room, with its long, leather banquette and wall of wine bottles, seats sixty; but there’s also an enclosed porch facing the water that’s a serene spot at any time of year. On one evening, the space was warmed by three-dimensional star-shaped lights overhead that were dimmed to make the porch a romantic setting. Just right for a special celebration.

Guests here are typically active. This high-energy crowd likes to hit the free continental breakfast and then burn off the calories outdoors.

Longshore was originally a private estate turned country club, until the town of Westport bought the land in 1960. But before it opened to the public, Longshore hosted celebrities such as F. Scott and Zelda Fitzgerald, Frank Sinatra and Marilyn Monroe.


195 Oenoke Ridge, New Canaan,

Like other centuries-old New England inns, The Roger Sherman has a long history of reinvention, and that lineage is one of the subjects that some patrons like to rehash over cocktails at the fine old bar in this 250-year-old landmark.

It was built in the eighteenth century as the home of Martha Sherman, the local minister’s wife and niece of Continental Congress delegate Roger Sherman. It then changed hands several times before a New York financier acquired the home in 1868 and upgraded the digs to satisfy his lifestyle, which was that of a Gilded Age tycoon. In 1925, the title passed to J. Herbert and Louise Stevenson Tebbetts, who converted the property to an inn. Hotelier John D. Shea bought the business from them but sold it in 1960 to New Jersey country club manager Roger Sherman Ross, a direct descendant of the original owner, for whom the property was named.

Through the centuries, Roger Sherman has maintained a reputation for fine dining, and it was that culinary connection that appealed to real estate investors Joseph and Nesreen Jaffre, who bought the place in 2008. The inn had some good years, but challenging times followed the last recession. So in 2014 when the Jaffres announced they would sell the inn, fans wondered if the antique building would be paved over for housing. Not so, as a celebrated chef recently recruited by the Jaffres is now attracting a new wave of patrons with his locally sourced menu and philopshy. Francois Kwaku-Dongo is an Ivory Coast-born culinary pro who gained international prominence in 1991 as executive chef at Wolfgang Puck’s Spago in West Hollywood. “We’re fortunate to have him,” says Nes Jaffre. “He’s brought his own philosphy and vision to the inn. He’s all about nature and nurture.”

The activity in the kitchen has spawned plans for remaking other areas around Roger Sherman, with its lovely rolling lawn and great location just a half mile from the center of the town of New Canaan. Updates to begin soon include the addition of vegetable and herb gardens for the chef, the expansion of the main dining room and a light makeover for the seventeen guest rooms, including new bathrooms, smart TVs and faster WiFi. “When you have a 250-year-old property, it always needs renovation,” says Jaffre. “But we don’t want to change the property so much that it’s unrecognizable. It’s been in existence for hundreds of years; it’s a historic landmark and one of the crown jewels of New Canaan. Guests will still find chocolates in their room at night and heated scones in the morning. We’re modern, but we’re still homey.”

“I love room 22, the honeymoon suite,” says Nes. “It is one of our deluxe suites, but you don’t have to be on your honeymoon to enjoy it.”

The food is a major draw at Roger Sherman, but live music on the weekends also pulls in a crowd. The musician from New Jersey is popular with guests who say he does Paul Simon songs better than New Canaan resident Paul Simon.

“Not many people know about our wine room,” says Nes. “It’s beautiful and seats up to thirty-five people for private events like birthdays and anniversaries.”

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