The Ultimate Litchfield County Day Trip Guide for Hikers (Views, Waterfalls & Small Town Stops)

Tired of the crowded trails at Sleeping Giant or the traffic on I-95? Tucked into the quiet northwest corner of Connecticut is a cluster of towns that feel like a secret. I live here, I hike these trails every week, and this is exactly how you execute the perfect Litchfield County day trip without wasting hours driving in circles.

This area is packed with mountain overlooks, quiet forest trails, waterfalls, and classic small towns that feel straight out of a postcard. You can hike a mountain in the morning, grab coffee in a historic town center, and still have time to catch a sunset view before heading home.

Whether you're planning a weekend adventure, a scenic road trip, or just looking for new hiking spots, this guide covers some of the best day trips in Litchfield County for hikers.

Quick Guide: Best Litchfield County Day Trips for Hikers

If you're short on time, these are some of my favorite places to explore in northwest Connecticut.

Kent – waterfalls, Appalachian Trail views, and a great small-town food scene

Salisbury – home to Connecticut’s highest peak and beautiful" mountain views

Cornwall – classic New England scenery and quiet Appalachian Trail hikes

Norfolk – peaceful forests, fire tower views, and fewer crowds

Washington – charming villages, scenic preserves, and rolling countryside

Litchfield – historic town green and beautiful nearby trails

Sharon - quiet countryside, Appalachian Trail access, and scenic nature preserves

Barkhamsted - deep forests, reservoir views, and peaceful hikes in northwest Connecticut

Town	Best For	Hiking Highlights
Kent	Waterfalls + food stops	Kent Falls, Macedonia Brook, Appalachian Trail
Salisbury	Big mountain views	Bear Mountain, Lion’s Head
Cornwall	Scenic overlooks	Pine Knob, St. John’s Ledges
Norfolk	Quiet trails + fire tower views	Haystack Mountain, Dennis Hill
Washington	Scenic preserves	Steep Rock Preserve, Hidden Valley Preserve
Litchfield	Historic charm + nearby trails	Mount Tom, White Memorial
Sharon	Peaceful preserves + AT access	Sharon Land Trust, Appalachian Trail
Barkhamsted	Deep forests + river hikes	People’s State Forest, Tunxis State Forest

Litchfield County is one of the best areas in Connecticut for hiking day trips because each town offers something different, from waterfalls and mountain summits to quiet nature preserves and scenic river trails.

Litchfield County Hiking Day Trip Itinerary

If you're visiting northwest Connecticut for the first time, it's easy to combine several stops into one perfect day trip.

Here’s an example itinerary that includes one of the most popular hikes in the area along with a few classic small-town stops.

Morning

Start your day with a hike at Lion’s Head in Salisbury, one of the best viewpoints in Litchfield County. Hike the shorter 2.3 mile trail or 4.4 mile trail along the Appalachian.

Lunch

Head to Kent for lunch and coffee. The town has several great cafés and restaurants and is a popular stop for hikers exploring the area. I love the buffalo cauliflower at Kent Pizza Garden Kitchen & Bar.

Afternoon

Visit Kent Falls State Park for a short walk through a small, red covered bridge to one of the most beautiful waterfalls in Connecticut.

Sunset

Finish the day with sunset views from Mount Tom or Apple Hill (White Memorial).

This route keeps driving time short while giving you a mix of mountain views, waterfalls, and small-town charm.

Map of the Best Litchfield County Hiking Day Trips

Explore the Best Hiking Day Trips in Litchfield County

Kent, Connecticut: Waterfalls, Appalachian Trail Views & Great Food

Kent is one of the most popular day trips in Litchfield County, and for good reason. The town has a little bit of everything: scenic hikes, waterfalls, historic bridges, and some of the best restaurants in the area.

Best Hikes in Kent

Kent Falls State Park

One of the most famous waterfalls in Connecticut. A short trail climbs alongside a series of cascading falls with multiple viewing platforms.

Macedonia Brook State Park

A great spot for a more challenging hike. Trails like Cobble Mountain offer incredible views over the surrounding hills.

Bulls Bridge & Schaghticoke Ridge

A quieter Appalachian Trail section with a scenic suspension bridge over the Housatonic River.

After the Hike

Downtown Kent has several great spots for a post-hike stop.

Grab flavored coffee at 52 on Main, or sit down for a meal at Swyft, one of the best restaurants in the area.

👉 Planning a trip here? Read my ultimate hiker's guide to the best things to do in Kent, CT

Salisbury, Connecticut: Connecticut’s Highest Peak

If you’re looking for big views, Salisbury is the place to go.

This town sits right on the Massachusetts border and is home to Bear Mountain, the highest point in Connecticut.

Best Hikes in Salisbury

Bear Mountain

The summit offers one of the best views in the state, especially in fall when the surrounding hills turn color.

Lion’s Head

A shorter hike with a rock ledge overlook that’s incredibly popular at sunrise.

Race Mountain

An Appalachian Trail hike with sweeping ridgeline views stretching into Massachusetts and New York.

Local Stops

Salisbury has a relaxed small-town vibe with great local businesses.

After your hike, stop by Sweet William’s Coffee Shop & Bakery for coffee and pastries.

Cornwall, Connecticut: Classic New England Scenery

Cornwall feels like a postcard version of rural New England. Rolling hills, old farms, and quiet forest roads make it one of the most scenic towns in Litchfield County.

Best Hikes in Cornwall

Pine Knob Loop

A relatively short hike with beautiful views over the Housatonic River Valley.

Mohawk Mountain

One of the most dramatic viewpoints in Connecticut. The wide open views of rolling mountains facing both North and South.

Don’t Miss

While you're in Cornwall, take a few minutes to visit the West Cornwall Covered Bridge, one of the most photographed bridges in the state.

Norfolk, Connecticut: Quiet Trails & Fire Tower Views

Norfolk is often called “the Icebox of Connecticut” because it tends to be cooler than the rest of the state, but it’s also one of the most peaceful places to hike.

Best Hikes in Norfolk

Haystack Mountain State Park

A short hike leads to a stone fire tower with panoramic views of the surrounding hills.

Dennis Hill State Park

Another great viewpoint with a historic pavilion and wide scenic vistas.

Because Norfolk is a little more remote, these trails are often much quieter than other Litchfield County hikes.

Washington, Connecticut: Scenic Preserves & Rolling Countryside

Washington is known for its beautiful countryside, historic architecture, and quiet nature preserves.

Best Hikes in Washington

Hidden Valley Preserve

A network of peaceful forest trails with picture-worthy bridges overlooks above the Shepaug River.

Steep Rock Preserve

One of the most beautiful preserves in the area, featuring riverside trails, stone tunnels, and scenic viewpoints.

Explore the Town

After hiking, spend some time exploring Washington Depot and New Preston, which has several small shops and cafés.

Litchfield, Connecticut: Historic Charm & Nearby Trails

The town of Litchfield is known for its historic town green and classic New England architecture.

It’s also close to several beautiful hiking areas.

Best Hikes Near Litchfield

Mount Tom State Park

A relatively short hike leads to a stone tower with incredible views over Bantam Lake.

White Memorial Conservation Center

Miles of peaceful trails through forests, fields, and wetlands.

Sharon, Connecticut: Quiet Appalachian Trail Views

Sharon is one of the most peaceful towns in Litchfield County, and it’s a great place to go if you’re looking for less crowded hikes and classic northwest Connecticut scenery.

Located along the New York border, Sharon has access to several beautiful sections of the Appalachian Trail, along with scenic rural roads and historic farms.

Best Hikes in Sharon

Sharon Land Trust

The Sharon Land Trust protects several beautiful preserves throughout town with peaceful forest trails, open meadows, and quiet natural areas. These preserves are perfect for slower walks and nature exploration, and they offer a different experience than some of the more rugged mountain hikes nearby.

Appalachian Trail – Sharon Section

Several trailheads in Sharon give access to peaceful stretches of the Appalachian Trail with wooded paths, ridgelines, and seasonal viewpoints.

After the Hike

Stop in Sharon Center to explore the historic town green, or grab food nearby in Kent or Salisbury to round out your day trip.

Barkhamsted, Connecticut: Forest Hikes & Reservoir Views

Barkhamsted is a hidden gem in northwest Connecticut, especially if you enjoy quiet forest hikes and scenic water views.

Much of the town is surrounded by protected land, including the massive Barkhamsted Reservoir, which creates some of the most peaceful landscapes in the state.

Best Hikes in Barkhamsted

Tunxis Trail

This long-distance trail runs through Barkhamsted and offers beautiful wooded hiking with occasional viewpoints. It's a great option if you’re looking for a less crowded alternative to more popular Litchfield County hikes.

American Legion State Forest & Peoples State Forest

Great place for easy to moderate hikes through classic New England forest. Trails here are especially beautiful in fall foliage season.

Don’t Miss

If you're already exploring Barkhamsted, consider taking a scenic drive around Barkhamsted Reservoir, one of the most picturesque areas in northwest Connecticut.

Tips for Planning a Litchfield County Hiking Day Trip

If you’re planning a day of hiking in northwest Connecticut, a little preparation can make your trip much more enjoyable.

Start early

Popular hikes like Bear Mountain and Lion’s Head can get busy, especially during fall foliage season.

Combine hikes with town stops

One of the best parts of visiting Litchfield County is exploring the small towns between hikes.

Check trail conditions

Some trails can be muddy in spring or icy in winter, so it’s always a good idea to check conditions before heading out.

Respect nature preserves

Many trails in the area are protected by local land trusts. Staying on marked trails helps protect the landscape so others can enjoy it too.

Best Time of Year to Visit Litchfield County

Litchfield County is beautiful year-round, but each season offers something a little different.

Spring – waterfalls and wildflowers begin to appear

Summer – lush forests and long daylight hours for hiking

Fall – beautiful foliage and scenic drives

Winter – quiet trails and snowy landscapes

Fall is easily the most popular season, especially for leaf peeping, so expect more visitors during peak foliage weekends.

Why Litchfield County is Perfect for Hiking Day Trips

What makes Litchfield County special isn’t just the hikes themselves, it’s the combination of mountains, small towns, and scenic drives that makes every trip feel like an adventure.

You can climb a rocky summit in the morning, wander through a historic town in the afternoon, and finish the day watching the sunset from a quiet overlook.

If you enjoy exploring places that feel a little wild but still welcoming, Litchfield County is one of the best areas in Connecticut to spend a day outdoors.

More Connecticut Hiking Guides

If you're looking for more places to explore nearby, check out these guides:

• Easy and beautiful Litchfield County hikes

• Scenic Northwest Connecticut trails

• Short hikes with big views in New England

Frequently Asked Questions on Hiking in Litchfield County

What is the best town in Litchfield County for hiking?

Kent and Salisbury are two of the best towns for hiking in Litchfield County thanks to their proximity to Appalachian Trail sections, waterfalls, and scenic mountain viewpoints.

Are there good day trips in Litchfield County?

Yes. Many towns in Litchfield County are close together, making it easy to combine hiking, scenic drives, and small-town stops in one day.

What is the most scenic hike in Litchfield County?

Popular scenic hikes include Bear Mountain, Lion’s Head, St. John’s Ledges, and Haystack Mountain.

Planning a trip to northwest Connecticut? Save this guide so you can come back to it when you're exploring Litchfield County.