The Connecticut shoreline can’t be beat.
That said, no visit to the area is complete without experiencing the charm of inland New England:
- The rambling farmland
- Charming village greens
- And Instagram-worthy covered bridges
The Litchfield Hills of Connecticut are dotted with:
- Sprawling countryside
- Unexpected waterfalls
- Jaw-dropping fall foliage
- Endless rolling hills
- 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 here.
About Litchfield County
On a map, Litchfield County is in the upper left corner of Connecticut.
This is an area 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.
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. 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:
- Burr Pond State Park, one of the best things to do in Torrington, CT
- Dennis Hill State Park
- And Haystack Mountain State Park in the town of Norfolk, CT
Other fantastic Connecticut hiking trails here include:
- Cathedral Pines Trail in west Cornwall
- 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
- The serenity of white spires piercing the blue skies
- 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 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 Litchfield, CT, all lovingly restored and preserved.
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:
- Wine tastings
- Exceptional dining experiences
- 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.
Who better to create the perfect sweet creamy treat than a pair who:
- Appreciate Carrie Bradshaw-worthy shoes
- 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.
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 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:
- Great Falls, known as the “Niagara Falls of Connecticut”
- Dean’s Ravine Falls, best viewed in the spring
- Spruce Brook Falls if you’re up to a more challenging hike
- Kent Falls, conveniently located near one of the area’s covered bridges
- Burr Falls when you need serenity now
- Knife Shop Falls with an easy hike and a three-for-one experience with three impressive “drops”
- 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 beauty of the Litchfield Hills
Travels in New England are not just about the shoreline.
The Litchfield Hills offer an authentic New England experience that is:
- Steeped in history
- Rooted in nature
- And bolstered by an eclectic variety of locally owned businesses
Discover more hidden secrets 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:
- Connecticut in the spring
- Connecticut in the summertime
- Connecticut in the fall
- Or Connecticut in the winter
We hope you enjoy your time, exploring all of the most unique things to do in Connecticut!