The Best Hiking Trails in Fairfield County, CT – Scenic Walks & Outdoor Escapes

Fairfield County offers more than beautiful homes and vibrant communities—it’s also a haven for those who love the outdoors. Here, hiking isn’t just about exercise; it’s about lifestyle. From expansive preserves that invite quiet reflection to lakeside paths perfect for family outings, the county’s trails strike a balance between refined natural beauty and everyday adventure.

Whether you’re looking for a serene escape that feels worlds away or a weekend activity the whole family (and even the dog) can enjoy, Fairfield County delivers. These trails combine accessibility with scenery, history, and a touch of luxury in the way only Connecticut’s landscape can.

1. Lucius Pond Ordway Devil’s Den Preserve (Weston & Redding)

Spanning 1,746 acres, this Nature Conservancy preserve is Fairfield County’s largest and most-trafficked (around 40,000 visits annually). With over 20 miles of trails winding through rich forests, rocky outcrops, and rare wildflowers—and habitats for bobcats, wood ducks, and pileated woodpeckers—it’s a perfect blend of serenity and wilderness immersion. Trail maps are available at the Pent Road entrance.

2. Aspetuck Valley Trail (Easton, Redding, Newtown)

This 5.9-mile Blue-Blazed trail follows the tranquil Aspetuck River, revealing scenic boggy landscapes, stone walls, and modest elevation changes. It threads through both Centennial Watershed State Forest and Aspetuck Land Trust land, offering a peaceful escape that's maintained by dedicated conservation partners.

3. Paugussett Trail (Shelton & Monroe)

A 13–14 mile Blue-Blazed hiking system that traverses Indian Well State Park, Webb Mountain Park, and serene greenways. Along the way, hikers encounter waterfalls, forested ridges, and even stair-assisted climbs. It’s ideal for longer explorations with a mix of gentle and moderate terrain.

4. Zoar Trail (Newtown – Sandy Hook area)

This 6.5-mile loop traces the border of Paugussett State Forest’s lower block. It skirts the shores of Lake Zoar and loops through dense, quiet woodland. Moderate in difficulty and rich in seasonal beauty, it’s a graceful choice for those seeking an intimate connection to nature.

5. Lillinonah Trail (Newtown)

Another Blue-Blazed gem, this 5.9-mile loop circles through Paugussett State Forest’s upper block. Expect elevated views over Lake Lillinonah, historic stone fences, a landmark “Great Oak,” and even a maple sugaring demonstration in season.

6. Lake Mohegan Loop & Fairfield Open Space Trails (Fairfield)

Tucked into the town, the 170-acre Lake Mohegan offers mixed-use trails, woodland, a small beach, and opportunities for nature observation and picnicking. It’s perfect for an easy, beautifully maintained local hike. Additionally, Fairfield itself manages over 1,250 acres of open space—including Brett Woods, Grace Richardson, and Hoyden’s Hill—with updated trail maps available for contemporary adventurers.

7. Norwalk River Valley Trail

This is the longest continuous trail in the county—30 miles stretching through Norwalk, Danbury, Wilton, Ridgefield, and Redding. Featuring paved and natural segments, it offers stroller-friendly pathways, scenic river views, and serves both casual walkers and seasoned hikers.

8. Huntington State Park (Redding/Bethel)

A local favorite—highlighted by outdoor enthusiasts as a “beautiful” setting featuring miles of trails, ponds, and rock formations. It's accessible, scenic, and offers a rustic charm for equestrians, dogs (leashed), and hikers alike.

Why These Trails Stand Out

Each trail offers something uniquely Connecticutan, balancing easy access with scenic tranquility—all fitting within an elevated lifestyle:

• Luxury meets heritage: Trails like Devil’s Den and Aspetuck Valley provide solitude and refined natural beauty.

• Versatility for all experiences: Whether you prefer lakeside strolls, extended forest wanderings, or family-friendly paved paths, there's a trail for every preference.

• Local stewardship: Many routes, especially Blue-Blazed ones, are cared for by conservation groups like the CFPA or Aspetuck Land Trust—highlighting both environmental and experiential value.

Final Thoughts

Hiking in Fairfield County is more than a pastime—it’s part of what makes living here so special. From peaceful lakeside loops to expansive woodland preserves, each trail offers its own way to slow down, connect, and enjoy the natural beauty that surrounds us. For some, it’s a weekend adventure with kids in tow. For others, it’s a wellness routine or a way to unwind after a busy day.

This blend of accessibility, scenery, and lifestyle is exactly what makes Fairfield County such a sought-after place to call home. Whether you’re considering a move, exploring a new neighborhood, or simply looking for your next outdoor escape, these trails are a reminder of the balance between nature and community that defines the area.