My Guide to Litchfield County
📍 Litchfield, Connecticut

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Litchfield County has become one of my favorite places to escape to in Connecticut. Just about an hour from Fairfield County, it has everything I want from a New England weekend. There are historic towns, winding country roads, beautiful inns, farm stands, excellent restaurants, antique shops, and vineyards. AKA, plenty of reasons to spend the day outside. Fall may get most of the attention, but this corner of Connecticut is worth visiting well beyond foliage season. Whether you’re planning an overnight escape or simply heading up for lunch and an afternoon of exploring, these are the places I’d put at the top of your list.

Where to Stay

The Abner Hotel

Right in the center of Litchfield, The Abner occupies the town’s former courthouse and is one of my favorite options if you want to be able to walk out the door and immediately explore. The interiors are colorful and playful without losing the character of the historic building, and having The Courtroom downstairs and Verdict on the rooftop makes it particularly easy to settle in for the night without getting back in the car.

Mayflower Inn & Spa

For a proper country retreat, it’s hard to beat the Mayflower Inn & Spa in Washington. Set on 58 acres of gardens and woodland, the property feels wonderfully removed from everyday life despite being an easy drive from New York and lower Fairfield County. Come for the beautiful rooms and grounds, stay for the spa, meals, fireside drinks, and the very convincing argument for not leaving the property at all.

Where to Eat

The White Horse Country Pub

If your vision of a Litchfield County weekend involves a cozy country pub, this is the stop. The White Horse has that wonderfully collected English-pub-meets-New-England feeling that makes you want to linger over lunch, particularly when the weather turns cool. It’s an easy place to work into a countryside drive and particularly good when you’re craving something relaxed.

West Street Grill

A longtime Litchfield institution, West Street Grill is one of those places that works equally well for a leisurely lunch or a proper dinner. I especially like it as part of a day spent walking around the center of Litchfield, since you can shop and explore before settling in for a meal.

Arethusa a mano

Arethusa a mano is the counterpart to nearby Arethusa al tavolo and a favorite stop when the day calls for coffee, pastries, or something quick. It’s makes an excellent first stop in the morning before heading out to explore Bantam and the surrounding countryside.

Espresso 59

Espresso 59 is a really great coffee stop in Litchfield. It’s an easy place to begin the morning or stop in between shops, whether you’re after coffee, something sweet, or a quick break before getting back on the road.

The Courtroom

Located inside The Abner, The Courtroom occupies the former historic courtroom and serves modern food and cocktails with an emphasis on local ingredients. Even if you’re not staying at the hotel, it’s worth stopping in for dinner or drinks. I’d follow it with a trip upstairs to Verdict, the hotel’s rooftop bar, when the weather cooperates.

The Garden Room

The Garden Room is worth visiting even if you’re not spending the night at the Mayflower. The light-filled dining room looks out toward the gardens and serves breakfast, lunch, and weekend brunch. Through the end of 2026, it is also hosting Café Boulud at the Mayflower, with Daniel Boulud’s French cuisine featured at dinner Thursday through Saturday. I’d happily build an entire morning around breakfast here followed by a drive through Washington and New Preston.

What to Do

Shop in New Preston

New Preston is tiny, but that’s part of its charm. Give yourself an hour or two to wander through the shops, look at antiques and homewares, and walk down toward the waterfall before lunch. It’s particularly easy to combine with Lake Waramaug, Washington Depot, or a meal at Community Table.

White Memorial Conservation Center

For some actual time outdoors, head to White Memorial in Litchfield and Morris. The preserve gives you miles of trails through woods, fields, and wetlands around Bantam Lake, so you can make the visit as leisurely or ambitious as you’d like. It’s especially beautiful when the leaves begin changing, but I’d keep it on the list year-round.

Averill Farm

If you’re visiting during apple season, Averill Farm is one of my favorite reasons to head to the area. Pick apples, grab cider and doughnuts, and enjoy the kind of straightforward orchard experience that doesn’t require turning the entire afternoon into a fall festival. It’s also surrounded by exactly the rolling Connecticut countryside you came to Litchfield County to see.

Arethusa Farm Dairy & Creamery

Arethusa is worth a stop for the ice cream alone. The dairy’s Bantam creamery is an easy addition to a day in Litchfield, and I would never object to building an afternoon around a scoop of ice cream and a drive through the countryside.

Sunset Meadow Vineyards

Head north to Goshen for an afternoon at Sunset Meadow Vineyards. The family-owned vineyard sits on 170 acres and produces estate-grown wines, with tastings available in its rustic tasting room and plenty of outdoor space on the lawn. Bring a blanket or chairs when the weather is nice and give yourself permission to stay awhile.

Kent Falls & Kent Falls Brewing

Make a day of the Kent area by pairing some time outside with a local beer afterward. Start at Kent Falls for the quintessential New England waterfall and covered-bridge scenery, then head toward Kent Falls Brewing for a much-deserved drink. This is one of my favorite combinations when you want your Litchfield County day to feel a little more outdoorsy.

Hollister House Garden

Garden lovers should make time for Hollister House in Washington. The garden has the intimacy and structure of an English garden while still feeling perfectly at home in the Connecticut countryside. It’s the sort of place where I’d allow plenty of time simply to wander rather than rushing through on the way to the next stop.

Thorncrest Farm & Milk House Chocolates

Thorncrest Farm is one of those wonderfully specific Litchfield County stops that makes a country drive more fun. The farm’s Milk House Chocolates are made using milk from its own cows. Stop in for a box to bring home, or, more realistically, a box you fully intend to bring home before opening it in the car.

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The best way to experience Litchfield County is not to try to do all of this in one weekend. Pick a few places, leave some room between reservations, and let the drive itself become part of the day. Stay in Litchfield and spend an afternoon around the Green, or base yourself in Washington and wander between New Preston, Lake Waramaug, farms, and gardens. Head north toward Kent when you want hiking and a country drive, or plan an entire day around apples, wine, ice cream, and a very good lunch. That’s what keeps me coming back: Litchfield County can be a romantic overnight, a family fall day, a long lunch with friends, or simply somewhere to drive when you want New England to look exactly the way you hoped it would. The scenery certainly helps, but it’s the combination of beautiful places to stay, genuinely good food, small businesses, farms, and the freedom to slow down that makes this part of Connecticut feel worth returning to again and again.

Love from Connecticut,
Katie

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