Amber in New England | Updated: November 2025

Litchfield County is filled with so many beautiful trails, but when winter hits the northwest corner of Connecticut, it becomes covered in a blanket of snow, sometimes making trails less accessible and difficult to traverse.

If you are looking for an easier but still beautiful trail to hike this winter, one of these seven options is a great place to start. These are the classic New England winter scenes you've been dreaming of, without the major elevation gains. Once you are properly prepared, get out and explore!

Welcome to Litchfield County, CT

Litchfield County is a cozy winter paradise! Picture rolling hills, charming towns like Litchfield and Washington, and classic New England architecture. The towns have a warm vibe, and the trails offer over 200 miles of paths. As you stroll, you'll soak in the history and the peaceful winter scenes of snow-covered trees and lakes, like a storybook come to life.

Essential Winter Hike Prep

Even though these trails are rated easy, preparing for them requires a winter-specific approach. The key to an enjoyable winter hike is proper layering and traction.

Whether you're a seasoned hiker or just eager to explore nature's winter wonders, these Litchfield County hiking trails are ready and waiting for your adventure.

The 7 Best Easy Winter Hikes in Litchfield County

1. Little Pond Boardwalk Trail (Litchfield)

• The Vibe: A friendly lollipop trail that goes around Little Pond, part of the White Memorial Foundation in Litchfield.

• Why It's Easy: This trail is about $1.2$ miles long, mostly on an elevated boardwalk that barely gains elevation.

• Winter Scene: During the winter, the trail is quiet and peaceful. You can hear birds chirping as you make your way around the loop. A perfect spot to soak in the peaceful vibes.

• GPS Directions [GPS Link]

2. Topsmead State Forest (Northfield)

• The Vibe: A gem perfect for a laid-back winter hike or an easy stroll. It’s like a mini-adventure for nature lovers and history buffs alike.

• Why It's Easy: Spread across 16 acres, you can wander through the woods, chill by the pond, and check out the grounds of a beautiful English Tudor style house.

• Winter Scene: The historic grounds covered in snow offer fantastic photo opportunities.

• GPS Directions [GPS Link]

3. Kent Falls State Park (Kent)

• The Vibe: If you are looking for a dramatic winter waterfall without a long, difficult hike, this is the place.

• Why It's Easy: The crown jewel of the region, Kent Falls boasts a series of cascading waterfalls. Only a few steps from the parking lot, you can take in this scene.

• The Walk: The trail leads you up a set of stairs and paths, winding through wooded areas and providing a few viewing points. A must-see!

• GPS Directions [GPS Link]

4. Campbell Falls State Park (Norfolk/Southfield, MA)

• The Vibe: Nestled in the quiet corner of Connecticut and straddling the Massachusetts border, the $100$-foot waterfall is surrounded by lush forests, making for a calm and peaceful experience.

• Why It's Easy: The trail leading to the falls from the main parking area in Southfield, MA, is short but rewarding.

• Pro Tip: Be warned—in the winter this trail can be icy. To add some mileage, opt to park at the trailhead off Spaulding Road in Norfolk and hike in about $0.5$ miles to the falls.

• GPS Directions [GPS Link]

5. Orenaug Park (Woodbury)

• The Vibe: The perfect opportunity to visit a fire tower without putting in the miles.

• Why It's Easy: Park on Park Road by the pond and take the Fire Trail between the two stone pillars. This trail is easy and direct, making it about $1.1$ miles roundtrip.

• The Reward: Once at the end, you're greeted by a $520$ foot fire tower, where you get a $360$ degree view of Pomperaug Valley. You also hike to two other viewing points looking out over the town.

• GPS Directions [GPS Link]

6. Fox Brook Trail System (Goshen)

• The Vibe: An awesome, customizable adventure by the Goshen Land Trust.

• Why It's Easy: This is a three-part system of easy trails:

  • John Ross Trail: About $3.6$ miles out and back.

  • Richard Kobylenski Wildlife Area: Around $2$ miles out and back.

  • Fox Brook Preserve: A quick $0.7$-mile escape.

• Highlights: These trails will lead you through the woods, across a couple of bridges, and alongside the river—a perfect playground to spot wildlife.

• Pro Tip: Parking for Fox Brook Preserve is tight; it's better to kick off from Pie Hill Road or East Street South for a longer hike. Be careful crossing the busy Route $4$.

• GPS Directions [GPS Link]

7. Barbour Woods (Norfolk)

• The Vibe: A series of easy trails throughout the forest and meadows.

• Why It's Easy: With so many trails, you can create your own hike, making it as long or short as your heart desires. The main parking area is off of Lovers Lane.

• Highlights: Look for scenic areas like the old stone arch bridge and views of Haystack Mountain across the street.

• GPS Directions [GPS Link]

When you are trying to plan your next winter hike, remember: it's not about the distance; it's about taking it easy and having a good time outdoors! Hope you enjoy your next winter adventure in Litchfield County.

Leave me a comment and let me know which trail you have done before or which one you hope to hike next.