Why Visit the Litchfield Hills?

Tucked up in the Northwest corner of Connecticut, the Litchfield Hills embody inland New England.  Postcard worthy small towns, plentiful waterfalls, rolling hills, village greens, covered bridges, farm stands, and exquisite fall foliage.  This. Is. New. England.

It doesn’t matter if you’re eating in one of the many villages that dot the countryside, walking the Appalachian Trail, or driving through rolling farmland, the scenery around you is bound to be the star attraction in the Litchfield Hills.  It’s beautiful.

On first glance, it may look like there’s not that much to do in the Litchfield Hills.  In some ways, that is the point.  This is a place to connect with nature and enjoy some relaxation in a quaint and bucolic setting.  If you are looking for a more diverting experience, however, the Litchfield Hills might prove to be a pleasant surprise.

Whether it’s hiking to a waterfall, roller coaster riding, skiing, picking fruit, or kayaking down a river, there should be enough to keep you occupied while you appreciate the views around you.  You never know, you might even want to come back for more.  You’re not coming to the Litchfield Hills for the nightlife, but…you already knew that, right?

Sunset over the Housatonic from West Cornwall

Sunset over the Housatonic from West Cornwall


Best Time to Visit

Fall.  Period.  Like so many places in New England, the already beautiful Connecticut landscape turns resplendent when the leaves turn.  While you certainly won’t have the area to yourself in the peak season, the ever present colors you’ll see will make up for any inconvenience that you feel from the modest crowds.

Outside of prime leaf peeping season, the Litchfield Hills are really a pleasure any time the weather is nice, and you can’t go wrong on a visit between Memorial Day and Labor Day.  There are things to do in the winter, but it’s definitely a slower season.  

WEEKEND Itinerary

If you’re looking for a break from a nearby city, a long weekend is the perfect amount of time spend in the region.  It’s enough time to hit some of the highlights while still enjoying the slower pace of life.  Assuming you get in late on Friday and leave Monday after lunch, click through for a good guide for the weekend.

Best Things to Do in the Litchfield Hills

Litchfield Hills Top 10

Litchfield Hills Leaf Peeping Travel Guide.JPG

1.  Go Leaf Peeping

The vast array of colorful leaves are a draw all across the Northeast, and with a combination of copious woodland, rolling countryside, and picturesque towns and buildings, the Litchfield Hills provide one of the best platforms in New England for viewing this spectacle.

While the most dramatic views involve lakes (Lake Waramaug is a favorite) or summits with 360° views (like Bear Mountain near Salisbury, Dennis Hill near Norfolk, and Cobble Mountain near Kent), beautiful vistas of the autumn leaves can be found almost anywhere.  Yes, hit the hot spots, but also just take some time to travel the backroads, and you won’t be disappointed.

Litchfield Hills Litchfield Post Office Travel Guide.JPG

2.  Explore Historic Litchfield

There’s no other spot in the region with as many in-your-face charms as Litchfield.

Start on the attractive village green with its impressive war memorials, and make sure you find the white spire of the Litchfield Congregational Church, one of the most photographed churches in New England.

The boutiques on West Street are worth checking out, and the impressive group of restaurants offer options from refined pub fare and treats to some of the best fine dining in the state.  Before you leave, make sure to check out the beautiful homes that line historic North and South streets.

If you’re in the region, plan on at least spending a few hours in this lovely town.

Campbell Falls

Campbell Falls

3.  Chase A Collection of Waterfalls

There are a number of noteworthy waterfalls in the region.  The numerous cascades of Kent Falls are the tallest in the state and extremely accessible, the Great Falls of the Housatonic got their name for a reason, and the rushing water just above Bull’s Bridge are a fun diversion from viewing the covered bridge over the river.

That said, our favorite waterfall experience is the moderate hike to Campbell Falls that crosses the Massachusetts border.  This double fall on the Whitney River is a relatively modest 50 feet tall, but the rush of water through the cleft in the rock is incredibly picturesque and photogenic.  Like every other waterfall in the state, it’s at its most powerful in early Spring. 

Litchfield Hills Arethusa Dairy Ice Cream Travel Guide.JPG

4.  Enjoy Ice Cream from Arethusa Dairy

Our family of self-proclaimed ice cream experts has had our share of good ice cream in the Northeast, but our favorite in the region comes from this branch of the Arethusa complex in Bantam.  Their website claims 16% butterfat is used to make this incredibly creamy ice cream that’s packed with flavor.  It truly is delightful.

In addition to ice cream, the dairy also sell a wide variety of cheeses, yogurts, and milk.

On a side note, you can visit the (often award winning) cows that produced your ice cream at the nearby Arethusa Dairy Farm near Litchfield.  Their hours are fairly limited, but you never know, the ice cream is so good that you may be tempted to pay your respects.

Bridge across the Shepaug River on the Bee Brook Loop

Bridge across the Shepaug River on the Bee Brook Loop

5.  Take a Hike

With the Appalachian Trail running through the area, you’re never too far away from great hiking.  From riverfront walks to mountaintop scrambles, these hikes are some of the best that the Litchfield Hills have to offer:

  • The Macedonia Brook Loop takes you past a flowing stream and through the forest to the top of Cobble Mountain

  • Walk the section of the Appalachian Trail that follows the Housatonic above Kent, a rare long stretch of this iconic path that follows a river

  • The Bear Mountain Trail is another section of the famed AT near Salisbury that takes you to Connecticut’s highest point

  • Hiking to the tower at the top of Mt. Tom to overlook Mt. Tom Pond and the beach below

West Cornwall Covered Bridge

West Cornwall Covered Bridge

6.  Marvel at Two Great Covered Bridges

At 242 feet long, the two-span bridge at West Cornwall is the longest covered bridge in Connecticut.  It was built in 1841, it’s still operating as a primary crossing of the Housatonic.  A little garden sits at the East end and provides a spot to gaze at the bridge and take the inevitable bevy of pictures.

Bull’s Bridge, built one year later in 1841 also crosses the Housatonic as it flows downstream.  Traffic negatively impacts your ability to admire the bridge from the ends, but a path running along the river allows for great views of the bridge’s span from below.  That said, be careful; the water runs very fast through this section of the river, and it can be dangerous.

These evocative and elegant structures take on a different character when you look inside.  The latticework appearance of these massive beams give you an indication of the engineering that went into building these marvels.There is also a small pedestrian covered bridge at Kent Falls State Park.  It’s pretty, but built in 1974, it’s far from historic.

Lake Waramaug

Lake Waramaug

7.  Grab a Canoe

The waterways of the Litchfield Hills are no less beautiful than the land, and the best way to experience the water is to be out in it.  If you don’t have a boat to bring to the region yourself, however, you’ll need to settle for the next best thing: renting one.

The beautiful Housatonic River is the main artery for the Western Litchfield Hills, and Clarke Outdoors provides the opportunity to experience it via canoe, kayak, or raft.  They offer various packages for full-day or half-day adventures for a reasonable price.

If you’re not interested in a trip down the river, the lakes of Litchfield County offer another opportunity to get out on the water.  Lake Waramaug State Park offers canoes for rental by the hour or the day.

Getting out on the water can be fun for any size groups including families with kids. 

Litchfield Hlils Trave Guide Scenic Drives.JPG

8.  Drive the Scenic Highways and Byways

Everywhere you turn, there will be a roadway winding up into the hills, meandering through rolling farmland, or following the path of a beautiful river valley.  It doesn’t matter whether you’re on one of the main roads or a narrow dirt track, you’re probably in for a treat.  Here are some favorites:

  • Hwy. 7 running North from Kent is a great drive.  It follows the course of the Housatonic and passes by Kent Falls and the covered bridge at West Cornwall. 

  • The scenic loop around Lake Waramaug has beautiful views of the lakes and the surrounding vineyards

  • The drive from Norfolk to Salisbury on Hwys. 44 and 41 offer some of the best farm scenery in the county

  • Hwys. 199, 67, and 133 take you over hills and through forests from Washington to Brookfield via Roxbury and Bridgewater

As a car is pretty much an essential companion in getting to and exploring the Litchfield Hills, you’ve already got what you need to get started.

Dawn Hill Antiques, New Preston

Dawn Hill Antiques, New Preston

9.  Shop an Antique Mecca

While you can find antique shops throughout the region, no town in the Litchfield Hills is more associated with antiques than Woodbury.  Literally dozens of shops dot the town center, and if you are interested in antique shopping, the more prominent shops like Mill House Antiques and Country Loft Antiques are definitely worth a stop for furniture and collectibles from the 17th and 18th centuries.

If you’re either not headed for Woodbury or it’s not enough to satisfy your antiquing desires, there are shops throughout the region with New Preston and Kent offering shoppers with a variety of options.

Hopkins Vineyard

Hopkins Vineyard

10. Go Wine Tasting on the Connecticut Wine Trail

While the wine industry in Connecticut may not be incredibly well known outside the state, wineries are popping up throughout Connecticut, and it is one of the fastest growing wine regions in the country.

Established in 1992, the Connecticut Wine Trail had 5 founding member wineries and has now expanded to more than 25 wineries across the state.  The Litchfield Hills are fortunate to have seven recognized wineries within its borders

Check out this map for all locations.  You can't go wrong on the trail, but both Hopkins Vineyard and Haight-Brown Vineyards make a great first stop.


Other things to do in the Litchfield Hills

Blueberries at Ellsworth Farm

Blueberries at Ellsworth Farm

The Housatonic near Cornwall Bridge

The Housatonic near Cornwall Bridge

  • Visit America’s Oldest Continually Operating Amusement Park at Lake Compounce

  • Pick Apples and Berries at a Local Farm

  • Ski at Mohawk Mountain

  • Camp at Lake Waramaug State Park

  • Ride a Snow Tube at Woodbury

  • Go Horseback Riding at Lee’s Riding Stables

  • Watch Road Racing at Lime Rock Speedway

  • Experience the Festivity of the Bethlehem Christmas Festival

  • Fly Fish the Housatonic

Church of Christ, Norfolk

Church of Christ, Norfolk

best towns in the Litchfield hills

The villages and towns of the Litchfield Hills have New England charm in abundance, and they should be a central focus of your time in the region.  Whether you're looking for antique shops, collections of restaurants, or historical churches, these towns have you covered.

While each town does have is unique in a way, you'll find that essential character almost everywhere you go.  Choose the towns that you go to based on your own preferences, but don't panic if you're not hitting ever single town.  No matter how many you hit, you will experience the New England way of life.

Sachem Farmhouse B&B, Warren

Sachem Farmhouse B&B, Warren

Where to stay in the Litchfield hills

You're not going to find any chain hotels here.  What you will find is a collection of inns and cozy bed and breakfasts that dot the pastoral landscape.  You won't find many budget options, but there are plenty of reasonable, mid-priced charming places to satisfy your needs and enhance your experience if you're not yet ready for the spectachular luxury resorts.

If you can't find what you need within the realm of traditional lodging, there is a good selection of vacation rentals to choose from to give you a bit more nuanced perspective.

If you're interested to hear our perspective on traditional lodging vs. vacation rentals, please check this out.

Poutine at the Kingsley Tavern, Kent

Poutine at the Kingsley Tavern, Kent

Where to Eat in the Litchfield Hills

As you might imagine, eating's good in this affluent corner of Connecticut.  Fine dining options outweigh cheap eats throughout the region, but there should be options to suit everyone.

New Milford, Litchfield, and Kent have the highest concentration of restaurants, but you can find something good in almost every town or village.

Getting to/around the Litchfield Hills

While theoretically possible to experience via mass transit, a car is necessary to get the best out of the Litchfield Hills.  I-84 runs along the southern border and is the primary mode that most visitors access the region. 

If you're coming from NYC or anywhere else to the South and West, you'll come up Hwy. 7 from Danbury, and New Milford will be your gateway.  From Boston and the major population centers to the East, Woodbury will likely be the first town you encounter via Hwy. 6.  There are a few ways in from the North and Northwest.

Once you're here, Hwy. 7 in the West, Hwy. 44 in the North, and Hwy. 202 through the middle will likely be your most heavily travelled thoroughfares, but there are numerous other ways to get where you need to go.  The good news is that almost every route you take will have a scenic beauty that made you glad you came.

St. Bridget's Church, Cornwall Bridge

St. Bridget's Church, Cornwall Bridge