Fairfield, CT —
The Perfect Saturday in Fairfield

Start with breakfast at the Driftwood Coffee Shop. It's a throwback old school Southport luncheonette, serving up delicious food in booths and round leather bar stools. Or just around the corner, have a cozy fall/winter brunch by the fire at the Gray Goose, a popular neighborhood haunt from morning til night. I get the corn flake french toast with local apples, cinnamon & vanilla bean butter. OH yes! At nighttime, this same spot heats up with a thirsty crowd enjoying cocktails on the front porch and inside at the bar.

After brunch, I’d zip to downtown Fairfield for some shopping. Embrace the Connecticut prep at Eliza B with poppy colors, custom sandals, purses, dog collars and headbands. Across the street is women’s clothing shop mainstay, The Snappy Gator, with shoes, bags and dresswear exhibiting timeless taste, a discerning quality and an all-around fresh feel.

For dinner, I’d highly recommend the Artisan at the Delamar Hotel in Southport. You can usually dine al fresco because of the heating lamps and fire pits dotting the outdoor seating area. Inside I like to grab a corner booth with my husband below the enormous handpainted mural of white tulips. We order the crab cake “a la plancha” with coriander chutney and avocado, the sea scallop risotto with English peas and the catch of the day with chorizo, mussels & calamari.

On our way home, we’ll stop at super popular Bodega in downtown Fairfield. Their Bodega Girl margarita is mixed with a strawberry-cilantro mash and my husband gets their Cabo Wabo Anejo on the rocks with lime.

Featured Listings

153 Ferry Road, Lyme (Hadlyme), CT

Welcome to Highover, a 30-acre hilltop estate on the lower Connecticut River designed by Alfred Hopkins. Over half a mile of water frontage makes this one of the most private waterfront settings in the state, with natural physical barriers that provide security and protection. Many notable guests have visited, including Albert Einstein, Katherine Hepburn, President Harding, and William Gilette. A 5-year renovation occurred at the sprawling 5 BED/8 BATH chateau residence and the 3 BED/4 BATH 1820s Federal Style guest house next to the pillared gated entry. The ground-up renovations exemplify the owners endless devotion to bringing the expected appurtenances into both homes while preserving their classic architecture. A new 3-bay garage with a workshop above and a spacious tobacco barn would accommodate many recreational needs. The dock on Whalebone Creek easily accommodates the owners 36 Hinckley Picnic boat. For larger boats, a 10-minute boat ride brings you to your mooring at Hamburg Cove, one of the Easts best hurricane holes. If your vessel is over sixty feet, marinas are available at the mouth of the river. Lyme is the quintessential enchanted classic New England setting of antique homes, stone walls, and undisturbed countryside. Uniquely poised between New York and Boston and a short ride to world-class entertainment at 2 of the world's largest casinos - Foxwoods & Mohegan Sun. Less than an hour by helicopter from JFK, Logan, and Bradley.

385 Harbor Road, Fairfield (Southport), CT

For 170 years, "Rose Hill" has graced the crest of Harbor Road, offering breathtaking views considered among the best on the East Coast. This magnificent Italianate landmark boasts 265 feet of direct waterfront access, complete with a private dock. Situated on nearly 2 acres, it stands as one of the largest and most commanding properties in Southport Village, offering unparalleled vistas of the Harbor, the Country Club of Fairfield golf course, and Long Island Sound. The meticulously restored Main House exudes charm and sophistication, featuring large public rooms with high ceilings that provide elegant spaces for entertaining. The spacious bedrooms and bathrooms offer stunning views, ensuring comfort and luxury. Additionally, a delightful guest apartment and wine cellar are located above the detached garage. Experience the epitome of refined living by dining al fresco, lounging by the pool, playing a game of bocce, tending to the garden, or relaxing on one of the many inviting porches. At "Rose Hill," every moment feels like a step back in time to an era when life was lived to its fullest. Sale also includes 331 Harbor Road (.55 acres). Seperate one bedroom guest house over the garage with kitchen and full bath (1,214 sq. feet) is not included in Main House square footage.

266 Michigan Road, New Canaan (Smith Ridge), CT

FURNISHED. Move In For Holidays! On 6+ acres, tailored for an American lifestyle this 18,000 SF European Style home is met inside w/a balanced mix of classic luxury and relaxed modern-day conveniences and furnishings accentuated by contemporary art. Curated by DDC-NYC from a global selection, the furniture was chosen in ways that maximize elegance, style, sophistication & functionality. Designed to host business associates and entertaining without sacrificing the on-going family activities, the home has two distinctive wings. North, with 2-Story Library, Conference/Reading rm, Main Office, Bar, Living and Music rms. Accessed via a separate courtyard, the South wing includes a Dining rm, Reception rm, 2nd Office, Valcucine ergonomic Kitchen, Breakfast area, Family rm, Back Staircase, Service/Mudroom. 2 Laundry rms. Primary Suite with Sitting rm, 2 Fireplaces, 2 Baths, WIC, Dressing rm and Terrace. 6 addit. En-Suites w/Porcelanosa Baths. Bespoke Millwork, Italian Chandeliers, Floor-to-Ceiling Paneled Walls, French Doors with Transom Windows. 8 Chesney Fireplaces. A family-wellness focused estate with enticing, extensive indoor and outdoor features & activities. Fitness Center w/Sauna. Viewing Anteroom leads to Game rm. Home Theater and Wine Cellar. Private fresh water Pond. Pool. Tennis Court. 2,000SF Cottage. Heated Garage with auto exhaust for 10 family cars or up to 25 collectible cars. Details incl. beds & baths on 266MichiganRoad.com. Unfurnished listing #170591063

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