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The Connecticut shoreline can’t be beat. That said, no visit to our state is complete without experiencing the charm of inland New England and Litchfield County, CT:
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The rambling farmland
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Charming village greens
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And Instagram-worthy covered bridges
The Litchfield Hills of Connecticut are dotted with:
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Sprawling countryside
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Unexpected waterfalls
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Jaw-dropping fall foliage
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Endless rolling hills
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And farm stands galore
As far as New England road trips go, the scenery and understated beauty of Litchfield Hills is one of Connecticut’s best-kept secrets. It’s on our list of the best road trips from New York City for a reason, after all.
Here are our insider tips on where you can explore the rich, natural beauty of the Litchfield Hills, CT. From the rolling hills and state parks to antique shops and ice cream cravings, there’s plenty to discover in the northwest corner of Connecticut.
About Litchfield County
On a map, Litchfield County is in the upper left corner of Connecticut. Or northwestern Connecticut, to be more precise.
The Litchfield Hills region is where history abounds. You’ll spot meticulously restored homes at every turn, and shady trees in village greens offer a quiet place to rest. It’s a short drive from Manhattan, and less overrun by tourists than the Hamptons.
A Brief History of Litchfield County
How It All Began
In 1751 Litchfield County officially came to life. Born from bits of Fairfield, New Haven, and Hartford counties, it gained its name from Lichfield in England. The town of Litchfield, CT, itself, though, got a head start back in 1719, when folks bought the land from the Tunxis Indians.
Revolutionary Days and a Busy Hub
By the American Revolution, and Litchfield County was abuzz. The town was a key spot for storing ammunition and even holding prisoners of war. The locals melted down a lead statue of King George III to make bullets, which removed all doubt as to their loyalties.
A Legal and Educational Pioneer
By 1784, Litchfield was making waves in the legal world with the country’s first law school, thanks to Tapping Reeve. This place churned out some big names, including future Supreme Court justices. Not to be outdone, the Litchfield Female Academy opened in 1792, giving women a shot at education when that was still a rarity.
19th Century Shake-ups
The 1800s brought some shuffling around with Litchfield County’s borders as new towns popped up and others found new homes in neighboring counties. When the Civil War rolled around, Litchfield proudly raised the 2nd Connecticut Regiment of Volunteers Heavy Artillery.
Modern Era
If you’re a fan of old buildings, modern Litchfield County has you covered. The county’s colonial and colonial revival architecture is a walk through a history book, showing off the good times after the Revolution and a cultural boom in the late Victorian era.
The best things to do in the Litchfield Hills of CT
Yet, you’ll discover a rich experience with top-tier dining, eclectic shopping, and more nature than you’ll ever hope to find this close to New York City. The Litchfield Hills embody New England charm, making it the ideal area to spend a day, a weekend, or a night out on the smaller town.
Antiquing for One of a Kind Finds
This is antique central, where treasures abound in almost every town. A favorite haunt for Connecticut antique lovers is Mill House Antiques in Woodbury, CT. This 17th–century grist mill offers an authentic antiquing experience. Curated original 18th centuries furniture and an eclectic inventory of home accessories are on offer. If you can’t get enough of Connecticut antique shops, Jeffrey Tillou Antiques in Litchfield has three whole floors to explore.
And the Litchfield Hills is right next door to another major center for antiquing, New York State. Kingston, New York, and Newburgh, across from Beacon, NY, are two great stops close to the Connecticut border with the Litchfield Hills.
State Parks and the Great Outdoors
Litchfield Hills is home to one of the most stunning segments of the Appalachian Trails. Running from Salisbury to Kent, you can hike to Bear Mountain or head to Norfolk to discover Connecticut state parks like:
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Burr Pond State Park, one of the best things to do in Torrington, CT
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Dennis Hill State Park
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And Haystack Mountain State Park in the town of Norfolk, CT
Other fantastic Connecticut hiking trails here include:
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Cathedral Pines Trail in West Cornwall
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Or White Memorial Conservation Center in Litchfield
If you’d rather take to the waters instead of hiking, the Housatonic River is ideal for outdoor activities involving kayaks and canoes. It’s all about taking your time to explore the meandering river valley and its breathtaking beauty.
Top Towns of Litchfield Hills
Regardless of what you’re looking for, from
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The serenity of white spires piercing the blue skies
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To the vibrant nightlife of local restaurants and hot spots
The charming small CT towns of Litchfield Hills never disappoint.
Are you a history buff?
Woodbury dates to the 1600s, taking pride in its past with plenty of Connecticut antique shops to explore.
Washington, CT, is famous for its iconic village green in the center of town, perfect for people watching. This is one of the towns that was a creative source for Stars Hollow of Gilmore Girls fame.
New Milford is the first town you’ll reach when traveling from New York. Just beyond Danbury, this town is one of the largest in Litchfield County. And yet, it offers a gorgeous feeling of small town Americana.
Kent holds the top spot for fall colors in New England, but also has a surprising selection of art galleries along its main street.
Lovely older homes dot the picturesque streets of the town of Litchfield, CT, all lovingly restored and preserved. Over 475 buildings in the district are on the National Register of Historic Places, in fact.
A few more small, cute, New England towns to discover up here include:
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Salisbury is a classic New England town, with scenic roads, vintage car races, ski jumping, and cozy inns. It’s the kind of place where you can relax or get active. And all while enjoying great food, local shops, and the many other things to do in Salisbury, CT. There’s a particularly gorgeous view from the Appalachian Trail here, if that gives you any ideas.
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Norfolk is small but packed with character. Highlights include Infinity Hall for concerts, cultural events like the Yale Summer School of Arts & Music, and a busy farmer’s market. Plus, they have a five-star library—who knew?
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Cornwall is famous for its covered bridge and Mohawk Mountain Ski Area, Connecticut’s largest ski resort.
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Falls Village might be tiny, but it’s rich in history and natural beauty. Don’t miss the Great Falls, Music Mountain, or the peaceful Isabella Freedman Jewish Retreat Center.
Really, you can just choose any route in the county, and you’ll end up finding something delightful.
Taste Connecticut Wine of the Litchfield Hills
While California is the heavyweight as an American wine country, Connecticut is carving a niche out for itself as an emerging East Coast wine area.
Known for fruit-forward varieties, you can tour the area hitting Connecticut vineyards offering:
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Wine tastings
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Exceptional dining experiences
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And stunning views of the hills
Haight-Brown Vineyard was the first winery in the state. It offers a selection of bold reds as well as limited edition fruit wines like Honey Nut Apple.
Wine aficionados know Sunset Meadows for its tempting wine “slushies” and stunning views. Meanwhile, Miranda Vineyard offers European heritage wines, with a nod towards Portuguese varieties.
You can find all these Connecticut wineries and more along the Connecticut Wine Trail.
The Covered Bridges of Litchfield County
A trip to New England calls for selfies at one of the enchanting, covered bridges along the Housatonic River.
If you plan things right, you can combine a fall leaf extravaganza with your covered bridge pics at Bull’s Bridge in the charming artistic town Kent.
The West Cornwall Covered Bridge is just as charming and much older.
Indulge in Connecticut’s Dreamy, Creamy Delights
Want the scoop on the best ice cream in Litchfield County?
We’ve got it.
Arethusa Dairy, in Bantam, CT, is where many New Yorkers plan an entire CT day trip to get just one lick of their beyond creamy, dreamy delights. This is not your everyday ice cream, with 16% butterfat adding a new dimension of impossible decadence.
Even more intriguing, the shop is the brainchild of two Manolo Blahnik executives who lived across from the dilapidated dairy.
They set their sights on improving their view and the result was Arethusa and the best ice cream in Connecticut.
Who better to create the perfect sweet creamy treat than a pair who:
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Appreciate Carrie Bradshaw-worthy shoes
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And have a burning desire to make everything beautiful?
A fall visit is highly recommended, so you can experience their seasonal Pumpkin with Ginger Molasses Cookies.
Divine.
Contemplate Life at One of Litchfield’s Waterfalls
What could be more Zen than staring into the beauty of a cascading waterfall?
This writer doesn’t like to play favorites.
And believe this writer that there are lots of CT waterfalls to choose from in the Litchfield Hills.
And yet, if the idea of trekking over treacherous rocks sounds like a bother, Campbell Falls is a good choice. It’s just a half-mile walk through cool, lovely woods before you reach the cascading waters. The falls are technically in Massachusetts, though you do park in Connecticut, so it still counts.
That said, there are many more waterfalls to discover, including:
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Great Falls, known as the “Niagara Falls of Connecticut”
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Dean’s Ravine Falls, best viewed in the spring
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Spruce Brook Falls if you’re up to a more challenging hike
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Kent Falls, conveniently located near one of the area’s covered bridges
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Burr Falls when you need serenity now
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Knife Shop Falls with an easy hike and a three-for-one experience with three impressive “drops”
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Nonnewaug Falls with its lush green mossy rocks and carpet of hemlock
Which you choose depends on how much energy you’re willing to put into your trip to the falls!
The Best Restaurants in the Litchfield Hills
Litchfield County is heavy on farm-to-table dining spots. Here are a few of the best spots to check out when hunger strikes:
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Arethusa al Tavolo, Bantam: Farm-to-table dining with fresh, local ingredients in a vibrant, welcoming setting.
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Clubhouse Provisions, Litchfield: Chef-owned modern steakhouse with American, Asian, French, and Korean influences. Don’t miss the miso black cod or heritage pork chop.
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West Street Grill, Litchfield: Modern American cuisine with fresh ingredients and a warm, inviting atmosphere.
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Meraki, Litchfield: Small café offering healthy, seasonal dishes—perfect for breakfast or lunch.
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G.W. Tavern, Washington Depot: Cozy American tavern known for hearty classics and a welcoming vibe.
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1754 House, Woodbury: Historic spot serving rustic American fare in a charming, relaxed setting.
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Litchfield Saltwater Grille, Litchfield: Family-friendly seafood restaurant with a great outdoor patio for warm weather dining.
Directions from Greenwich, CT, to the Litchfield Hills
I’m glad we got you interested in a day trip to the Litchfield Hills from our Greenwich CT, bed and breakfast! The drive is pretty easy and should take you about 1.5 to 2 hours, depending on where you’re headed. You can take I-95 or the Merritt Parkway northbound to either Route 7 north from Norwalk, or Route 8 north from Bridgeport.
Hotels, Inns, & Unique Places to Stay in the Litchfield Hills Region
If you’re heading to Litchfield County, here are some standout places to stay:
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Winvian Farm, Morris: Set on 113 acres, Winvian Farm offers themed cottages, a spa, and fine dining—perfect for a luxury escape.
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The Hopkins Inn, Warren: Overlooking Lake Waramaug, The Hopkins Inn features rustic charm and Austrian cuisine in a picturesque setting.
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The Litchfield Inn, Litchfield: A blend of classic New England and modern comfort, The Litchfield Inn hosts a scenic and relaxing stay.
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The White Hart Inn, Salisbury: One of the oldest inns around, The White Hart Inn mixes historic charm with contemporary amenities, perfect for weekend getaways in New England for couples.
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The Cornwall Inn, Cornwall: This peaceful retreat offers cozy rooms and a welcoming atmosphere, perfect for unwinding.
Discover more hidden gems of Connecticut
The Litchfield Hills area is an ideal weekend road trip spot to escape to regardless of the time of year. Each season makes the area feel like an entirely new locale.
So whether you’re planning your visit to:
We hope you enjoy your time, exploring all of the most unique things to do in Connecticut!
You can also continue north to the Berkshires of Massachusetts, and go even deeper into the Berkshire Mountains on the Massachusetts side. Or head west from here into the Hudson Valley. All these historic places and villages have delighted visitors for centuries. I’m sure they will charm you, too!
