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Tuesday, August 30, 2022

Weekender's Guide: Northwest Connecticut/The Litchfield Hills

When I lived in Utah, I had a hard time describing Connecticut to people. It's sandwiched between New York, Massachusetts, and Rhode Island but it truly has its own identity. The shoreline shifts from a suburb of New York to an extension of Rhode Island. The central area (especially around the Connecticut River) is quaint and iconic, filled with old towns and historic homes. The northeast corner has been dubbed the "quiet corner" and it's known for exactly that.

But the northwest corner is my favorite part of the state. It's known for rolling hills, sleepy towns, and boarding schools that resemble college campuses. This tiny corner is where you can find old covered bridges, quiet country stores, and old romantic inns. The Housatonic River snakes through the area and Route 7 offers a scenic drive of fly fishermen and summer sunbathers. Once you leave the river, you can follow 50 miles of the famous Appalachian Trail and hike to the state's highest point. It's a gem year round but my favorite time is fall. The bugs are gone, the leaves are turning, the apple orchards are open, and bonfire season is in full swing. It's an area I keep coming back to, for a day hike any time of year or an overnight excursion in the summer. 

View of the Housatonic River from the covered bridge

Hiking in Macedonia State Park

The area we call "The Litchfield Hills" consists of 21 communities: Barkhamsted, Burlington, Canaan, Colebrook, Cornwall, Goshen, Hartland, Harwinton, Kent, Litchfield, Morris, New Hartford, Norfolk, North Canaan, Roxbury, Salisbury, Sharon, Torrington, Warren, Washington, and Winchester. 


Disover Litchfield Hills has an awesome interactive map if you want to see what exactly is around while exploring. If you want a little more direct guidance, here is my suggested "weekend itinerary". Follow it loosely and in true Katie Wanders fashion, make it yours. Keep scrolling down to see a list of suggested hikes, favorite places, and some worthy stops while visiting this little slice of paradise. 

White Memorial Conservation Center

Weekend Itinerary 


Head up the northwest corner of Connecticut. Stop through Cornwall, make a stop at the cutest general store, and see the historic covered bridge with the view of fly fishermen enjoying the sunshine on the Housatonic River. If you have time in the evening, plan a short hike (Pine Knob Loop is a great option). 

Housatonic River

Pine Knob Loop Hike


Plan a morning hike (a hike along the famous Appalachian Trail is a great option while visiting this area). Head to Goshen and check out Thorncrest Farm and Milk House Chocolates. Meet the dairy cows and grab some chocolates for the road. If you have kids in the group (or young at heart), stop at Action Wildlife (Goshen) to pet the goats, and feed a few Zebras along with other exotic animals. For dinner, head down to Kent and check out the town, have an amazing craft beer at Kent Falls Brewing, stop to see the waterfall at Kent Falls State Park, and grab dinner at Fife' n Drum (pet-friendly outside). 

Lover's Leap State Park


Start the morning at White Memorial Conservation Area. Enjoy a hike around the boardwalk and take in the scenery. Head to Litchfield and grab a meal at Village Restaurant (great food with a casual vibe right off the town green). Keep the party going and head to Arethusa Farm Dairy for some of their famously good ice cream. If you have time, stop in Washington for a quick hike through Hidden Valley Preserve to the Henry David Thoreau Footbridge

White Memorial Conservation Center

Macedonia Brook State Park

Here are some hikes, activities, and places to eat if you want to "mix and match" your adventure up in the northwest corner.


Pine Knob Loop (Sharon): 2.6 miles 
Rand's View (Canaan): 5.5 miles
Bear Mountain (Salisbury) (tallest peak): 6 miles 
Backpacking along the AT - 10-mile River Shelter (Kent): 6 miles 
Macedonia Brook Loop (Kent): 6.5 miles
Round Mountain (Salisbury)- tri-state hike: 5.4 miles
Mohawk State Forest (Goshen): Scenic drive up the mountain to the summit with small hikes as you go. 
White Memorial Conservation Area (Litchfield): 1.5-4 miles
Meeker Trail Loop Macricostas Preserve (Washington): 1/2 to 2 miles 4.5 miles 

Bull's Bridge


Averill Farm (Washington Depot): a tenth-generation farm and is the perfect place to go apple picking in October. You can also find pumpkins, mums, cider and cider donuts on the property.
Kent Falls Brewing Company (Kent): fantastic working farm brewery
Arethusa Farm Dairy (Litchfield): full fledge dairy farm known for their icecream
Kent Falls State Park: gorgeous state park with a waterfall and picnic areas
Thorncrest Farms and Milk House Chocolates (Goshen): Quaint dairy farm known for their chocolate - great spot for the kids to see the dairy cows
Macedonia Brook State Park (Kent): Scenic state park with a winding brook, camping, and awesome hiking
Lovers Leap State Park (New Milford): Small state park known for its scenic wrought iron truss bridge.  
West Cornwall Covered Bridge (West Cornwall): 1 of 3 covered bridges in Connecticut
Bull Bridge Kent: 1 of 3 covered bridges in Connecticut
Housatonic Anglers (Cornwall): half-day or full-day fishing trips on the Housatonic River and tributaries. Newbie? You can also take fly fishing lessons. 
Clarke Outdoors (Sharon): Kayak, canoe and raft rentals. You can also partake in a 10-mile trip from Falls Village to Housatonic Meadows State Park. 
Haight-Brown Vineyard (Litchfield): Connecticut's first winery - visit for tastings, tours, and special events 
Windfield Morgan Farm (Litchfield): Trail rides and pony rides 
Lime Rock Park (Salisbury): Road Racing at Lime Rock Speedway

Cornwall Country Market


The Village (Litchfield): Pub grub and contemporary American food. Fairly priced and something for everyone. 
West Street Grill (Litchfield): Upscale new American right on the green. 
Winvian (Morris): Fine dining on the farm 
Mayflower Grille (Washington): Romantic upscale restaurant at the famous Mayflower Inn & Spa. 
Good News Cafe (Woodbury): Farm-to-table cuisine  
Kingsley Tavern (Kent): Elevated pub grub 
Fine 'n Drum (Kent): Straightforward food in a nice setting - outdoor seating downtown Kent

Macricostas Preserve

Hidden Valley Preserve

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