Two Day Summer Trip in Litchfield County: A Dreamy Getaway

There is a rhythm to summer in Litchfield County—a cadence of slow mornings, golden-hued afternoons, and evenings that hum with warmth and quiet luxury. A place where time seems to stretch, inviting you to linger just a little longer, to savor just a little more.

Day One: Sun-Kissed Vineyards & Pastoral Pleasures

Ease into the day with a glass of something exceptional at Sunset Meadow Vineyards. Rolling hills cradle rows of sun-drenched vines, where estate-grown grapes are transformed into wines that whisper of the land’s quiet elegance. Sip a Cayuga White as you settle into the moment, the vineyard stretching wide beneath the open sky.

From here, a short drive leads to Arethusa Farm Dairy, where the scent of fresh cream lingers in the air. Here, tradition is honored in its purest form—handcrafted cheeses, velvety ice creams, and milk fresh from the pastures. Pause, indulge, and perhaps take a little something with you—a taste of this place to bring home.

A slow afternoon calls for a visit to Milton Market, a hidden gem of artisanal finds and seasonal bounty. From local honey to handmade pastries, every item tells a story of the land and the people who call it home. Gather provisions for an impromptu picnic or simply let yourself wander, guided by curiosity.

As twilight descends, dinner unfolds at Community Table—a culinary homage to the fields and farms of Litchfield County. The menu, ever-evolving, is a reflection of the season’s best, prepared with a reverence for simplicity and flavor. Candlelight flickers, conversation lingers, and the evening settles into a quiet symphony of contentment.

Day Two: A Town Steeped in Story & Nature’s Embrace

The morning unfurls gently in Downtown Litchfield, where history is etched into cobblestone streets and colonial façades. Boutiques and galleries beckon, offering carefully curated collections of art, textiles, and antiques—each piece imbued with a sense of place.

The afternoon leads to the heart of nature at White Memorial Conservation Center—forty miles of woodland trails, winding past still ponds and whispering pines. Time slows here, the hush of the forest urging you to move at its unhurried pace. Pause by the water’s edge, let the cool breeze brush against your skin, and simply be.

Return to The Litchfield Inn, where familiar comforts await—an inviting armchair, a soft-lit corner, the kind of stillness that allows the memories of the past two days to settle, to root. As dusk falls and the stars punctuate the night sky, the feeling remains: Litchfield is not a place to rush through—it’s a place to return to, time and time again.

BOOK YOUR STAY