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Western Connecticut Planning Region

Taylor Corners

The best walks and hikes around Taylor Corners

By Fede from komoot

·

Updated June 1, 2026

If you've ever tried to plan hiking around Taylor Corners, you know how overwhelming the options can be. It’s tough to tell which routes are genuinely worth your time and effort, and which are just filler. We get it – you want to hit the trails that offer the best views, the most rewarding climbs, or simply a peaceful escape. That's exactly why we put this guide together.

Our komoot community has explored, mapped, and reviewed countless routes here, so consider this your curated shortcut. We've sifted through the data to bring you a shortlist of trails that are truly worth your legs, saving you the guesswork. Hiking around Taylor Corners means exploring a beautiful mix of woodlands and freshwater lakes, with varied terrain that ranges from gentle strolls to more challenging climbs. You'll find everything from easy, family-friendly paths to moderate routes that offer a good workout, all within the scenic landscape of New Fairfield, Connecticut.

If you only do one hike, make it the Pootatuck State Forest Loop. At 4.1 miles (6.6 km) with 665 feet (203 m) of climb, it's our most popular moderate route and a fantastic introduction to the area's diverse woodlands. For a different feel, the Pine Hill to Squantz Pond Loop, at 4.3 miles (6.9 km) and 711 feet (217 m) of elevation gain, is a top favorite for its rewarding views of Squantz Pond. Ready to explore? Dive into these routes and discover why more than 40 hikers have already used komoot to experience Taylor Corners.

If you only do 3 of these routes

  1. 1

    Pootatuck State Forest Loop
  2. 2

    Cranberry Mountain Trail
  3. 3

    Bear Mountain via Red, White, and Yellow Trails Loop

Compare these routes at a glance

Trail

Distance

Elevation

Difficulty

Pootatuck State Forest Loop

6.55 km

200 m

Moderate

Cranberry Mountain Trail

5.87 km

100 m

Easy

Bear Mountain via Red, White, and Yellow Trails Loop

3.21 km

70 m

Easy

Pine Hill to Squantz Pond Loop

6.92 km

220 m

Moderate

Farringtons Woods Trail

1.76 km

20 m

Easy

Michael Ciaiola Conservation Area Trail

8.59 km

330 m

Moderate

Boggs Pond Red Trail Loop

1.90 km

30 m

Easy

Sweetcake Mountain White Trail

1.03 km

70 m

Easy

Squantz Pond Trail

3.76 km

60 m

Easy

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1.

Pootatuck State Forest Loop

6.55km

02:01

200m

240m

The Pootatuck State Forest Loop offers a tranquil escape into a landscape of rugged, wooded slopes and fascinating rock formations. As you hike, you'll traverse shaded paths, old charcoal-wagon roads, and wider fire roads, eventually reaching a stunning rock outcrop with panoramic views of Squantz Pond and Candlewood Lake. Keep an eye out for seasonal streams and waterfalls, especially after rain, adding to the picturesque scenery.

This moderate 4.1-mile (6.6 km) loop, with 666 feet (203 metres) of elevation gain, typically takes around 2 hours. While manageable for those with good fitness, be ready for some short, steep descents and sustained ascents. Sturdy shoes are recommended for the uneven and rocky terrain, ensuring a comfortable and safe experience on the Pootatuck State Forest trails.

Beyond the scenic overlooks, the Pootatuck State Forest is rich in history, with trails that include paths built by the Civilian Conservation Corps in the 1930s. The forest boasts a diverse ecosystem of oak, maple, and birch trees, and its name, an Algonquian term meaning "river of the falls," hints at the natural features you might encounter. It's a peaceful alternative to more crowded areas, perfect for wildlife spotting.

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2.

Cranberry Mountain Trail

5.87km

01:37

100m

90m

The Cranberry Mountain Trail offers a delightful and varied hiking experience, winding through lush forests and crossing serene streams before opening up to panoramic views of the Hudson Valley. This easy 3.6-mile (5.9 km) loop, with a gentle 323 feet (99 metres) of elevation gain, is perfect for a quick escape into nature, providing rewarding vistas without a demanding climb. You'll find smooth forest paths transitioning to some rocky sections, making for an engaging journey.

Planning your visit is straightforward, as the trail is easily accessible from major population centers and features ample parking at the trailhead. While it's an easy route, sturdy hiking boots are advisable for comfort on varied terrain. The best time to hike is during spring for wildflowers or fall for vibrant foliage, though it's generally enjoyable year-round.

This trail stands out for its well-maintained system, thanks to the USDA Forest Service, ensuring a pleasant experience for all. It's an ideal choice for families or beginner hikers looking for a scenic outing that takes approximately 1 hour and 36 minutes. The route provides excellent opportunities for wildlife observation and offers some of the best viewpoints in the Cranberry Mountain area.

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3.

Bear Mountain via Red, White, and Yellow Trails Loop

3.21km

00:54

70m

70m

The Bear Mountain via Red, White, and Yellow Trails Loop offers a delightful and accessible hike through the scenic Bear Mountain Reservation. You'll experience a mix of paved paths and gentle woodland trails, providing a refreshing escape into nature. It's an ideal route for those seeking a tranquil walk with forest views, perfect for a quick outdoor break.

This easy 2.0-mile (3.2 km) loop involves a modest 218 feet (66 metres) of elevation gain and can be completed in about 54 minutes. It's a great choice for a relaxed outing, suitable for all ages and fitness levels. Plan to arrive early for parking, especially on busy days, to ensure a smooth start to your adventure.

Bear Mountain State Park is a significant area, known for its natural beauty and accessibility from urban centers. This particular loop provides a taste of the park's charm without the strenuous effort of its more challenging routes. It's a fantastic way to enjoy the fresh air and forest environment, making it a popular choice for a short, rewarding hike.

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5.

Farringtons Woods Trail

1.76km

00:28

20m

20m

Step into the tranquil embrace of Farringtons Woods Trail, an easy 1.1-mile (1.8 km) hike that winds through a lush green forest near the New York-Connecticut border. This short route, with only 54 feet (16 metres) of elevation gain, offers a quick 28-minute escape into nature, featuring beautiful views of Sanford Pond and even an amazing waterfall. You'll enjoy the peaceful atmosphere created by tall trees and dense underbrush, with sunlight filtering through the canopy.

While the specific 1.1-mile loop is easy, the broader Farrington Woods area is a multi-use park with varying trail difficulties, so be mindful of other users like mountain bikers. Signage can be limited, so it's wise to bring a map or use a navigation app to ensure you stay on your intended path. Visiting during off-peak hours is recommended for a quieter experience and better parking availability.

Beyond the natural beauty, the trail system holds historical intrigue with old ruins scattered throughout, including the site of the former Putnam Rod & Gun Club. This blend of natural scenery and historical elements makes Farrington Woods a unique destination within the Western Connecticut Planning Region, offering more than just a simple walk in the woods.

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6.

Michael Ciaiola Conservation Area Trail

8.59km

02:43

330m

330m

The Michael Ciaiola Conservation Area Trail offers a wonderfully diverse hiking experience, winding through a mixed hardwood forest that feels both serene and alive. You'll navigate gently rolling hills and some rocky sections, but the reward is a journey past stunning waterfalls, including the great gorge waterfall, and numerous cascades along the stream. This moderate 5.3 miles (8.6 km) route involves 1072 feet (327 metres) of elevation gain and typically takes around 2 hours and 43 minutes to complete, making it an ideal choice for those seeking natural beauty without an all-day commitment.

When planning your visit, remember that conditions can vary; expect muddy or icy patches in winter and be prepared for ticks during warmer months. Dogs are permitted on a leash, and you'll find parking available at the Great Hollow and Michael Ciaiola parking areas. Spring is particularly lovely for wildflowers, but the area offers excellent birdwatching opportunities throughout the year.

This 800-900 acre conservation area is a haven for wildlife, encompassing forests, wetlands, and streams, including a portion of the Great Swamp, one of New York's largest freshwater wetlands. You might spot deer, turkey, bobcats, or various songbirds. The interconnected trail system allows you to tailor your hike, from flatter, family-friendly paths to more challenging, steeper sections, ensuring there's something for every preference.

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7.

Boggs Pond Red Trail Loop

1.90km

00:31

30m

30m

The Boggs Pond Red Trail Loop offers a truly pleasant and accessible hiking experience, perfect for when you need a quick dose of nature. As you walk, the path hugs the serene waters of Boggs Pond, providing continuous peaceful views. The terrain is generally flat or gently rolling, making it an easy 1.2-mile (1.9 km) loop that feels refreshing and calm.

Planning your visit to this easy trail is straightforward, as it is located in Richter Park in Danbury, Connecticut. You will find parking available at the park, making trailhead access simple. With an estimated duration of just 31 minutes and only 101 feet (31 metres) of elevation gain, it is an ideal choice for a spontaneous outing any time of day.

This trail stands out as a fantastic option for a relaxing stroll, especially for families or anyone looking for a low-impact walk. Its primary appeal lies in its tranquil waterside setting and easy accessibility, providing a quiet natural escape within the Danbury area without requiring significant time or effort.

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8.

Sweetcake Mountain White Trail

1.03km

00:21

70m

20m

Wander through the serene deciduous forests of Sweetcake Mountain Lake Preserve on the Sweetcake Mountain White Trail, where the path gently rises and falls. You'll encounter charming rock outcroppings before reaching the true reward: a sweeping panoramic vista of Candlewood Lake from the summit. It's a tranquil escape, perfect for soaking in the natural beauty of New Fairfield woods on an easy 0.6-mile (1.0 km) route with 221 feet (67 metres) of elevation gain, taking about 20 minutes.

Planning your visit to the Sweetcake Mountain White Trail is straightforward, as it's located in a quiet neighborhood with accessible parking. This easy trail is suitable for families and is dog-friendly, making it a great choice for a quick outing. Consider visiting in the morning for the most peaceful experience, though it's enjoyable any time of day.

Beyond the scenic views, the preserve holds a special significance with the "Fox Family Memorial," an inscribed bedrock outcrop honoring Dorothea and Charles Fox, whose family donated the land for public enjoyment. This adds a layer of local history to your hike, complementing the diverse open deciduous forest, dense mountain laurel understory, and hemlock stands you'll pass through.

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9.

Squantz Pond Trail

3.76km

01:02

60m

60m

The Squantz Pond Trail offers a compact, mountain-like hiking experience within Squantz Pond State Park, delivering diverse terrain and stunning water views. This easy 2.3 miles (3.8 km) route, with 209 feet (64 metres) of elevation gain, takes about 1 hours and 2 minutes to complete, but don't let the easy rating fool you entirely; sections are surprisingly rugged with rocky paths, steep slopes, and even some rock scrambles. You'll be treated to expansive views of Squantz Pond and even Candlewood Lake from various rock outcrops, making it a rewarding outing for its length.

Planning your visit is straightforward, with the trail accessible within Squantz Pond State Park. While specific parking details aren't provided, arriving earlier in the day is always a good strategy, especially during popular times. Autumn is particularly recommended for the vibrant fall foliage reflecting on the pond, creating a picturesque backdrop for your hike. Be aware of general park signage and conditions, especially near the water's edge.

This trail is part of a larger system that connects to the adjacent Pootatuck State Forest, offering options for longer explorations if you're feeling ambitious. Along the route, you'll encounter interesting geological features and the historic Council Rock, a massive boulder once used by the Schaghticoke Tribe for gatherings. The blend of natural beauty, varied terrain, and historical context makes the Squantz Pond Trail a unique and engaging hike in Western Connecticut.

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Tips from the Community

Sue
June 18, 2025, Bear Mountain Reservation

Bear Mountain Reservation spans 140 acres, with fantastic hiking trails and scenic overlooks. The red trail loops through woods and open fields, while the orange trail leads to stunning views of Candlewood Lake. There are picnic tables and beautiful wildflowers, especially in the spring, and is an ideal spot for birdwatching. While you're here, you may spot a few hawks and even a golden eagle if you're lucky.

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Frequently Asked Questions

How many hiking trails are available around Taylor Corners?

Taylor Corners offers a selection of over 10 hiking routes, catering to various skill levels. You'll find a mix of easy and moderate trails, providing diverse options for exploring the natural beauty of the New Fairfield area.

Are there easy hiking trails suitable for beginners or families in Taylor Corners?

Yes, Taylor Corners has several easy trails perfect for beginners or families. For instance, the Cranberry Mountain Trail is an easy option, offering a pleasant walk through the local landscape. Another short and accessible choice is the Farringtons Woods Trail.

What kind of natural features or attractions can I expect to see on hikes near Taylor Corners?

Hiking around Taylor Corners often brings you close to beautiful natural features. Many trails offer views of lakes like Squantz Pond, which is part of the larger Squantz Pond State Park. You might also encounter serene woodlands and diverse wildlife. Specific highlights include Squantz Pond State Park and Parks Pond and Picnic Site.

Are there any circular hiking routes in the Taylor Corners area?

Yes, you can find circular routes that allow you to start and end at the same point. A popular loop is the Pootatuck State Forest Loop, which takes you through varied terrain. Another excellent option is the Pine Hill to Squantz Pond Loop, offering scenic views of the pond.

Are hiking trails around Taylor Corners dog-friendly?

Many trails in the Taylor Corners region, particularly within state parks and preserves like Pootatuck State Forest and Great Hollow Nature Preserve, are generally dog-friendly. However, it's always recommended to check specific park regulations or trail signage for the most current rules regarding pets, and to keep dogs on a leash.

Are there any hiking trails with waterfalls near Taylor Corners?

While specific waterfall trails within Taylor Corners itself are not highlighted, the broader region within a 50-mile radius is known to have approximately 19 waterfall hiking trails. These range from easy to moderate difficulty, and many are dog-friendly, offering opportunities to discover scenic cascades.

What do other hikers say about the trails in Taylor Corners?

The hiking routes in Taylor Corners are highly regarded by the komoot community, boasting an average rating of 5.0 stars. Hikers often praise the diverse terrain, the peaceful atmosphere of the woodlands, and the scenic views, especially around Squantz Pond.

What is the best season for hiking in Taylor Corners?

The Taylor Corners area offers beautiful hiking experiences throughout the year. Spring brings lush greenery, while summer is ideal for combining hikes with water activities at nearby lakes. Fall is particularly stunning, with vibrant foliage creating spectacular scenic views. Even winter hiking can be rewarding, especially in Pootatuck State Forest, though trail conditions should be checked.

Are there any longer, more challenging hikes available?

For those seeking a longer and moderately challenging experience, the Michael Ciaiola Conservation Area Trail is a good option. This 5.3-mile route leads through a conservation area, providing a more extended exploration of the local landscape.

Where can I find parking for hiking trails in Taylor Corners?

Parking is generally available at the access points for state parks and nature preserves in the Taylor Corners area. For example, Squantz Pond State Park and Pootatuck State Forest typically have designated parking areas for visitors. It's advisable to check specific trailheads or park websites for detailed parking information before your visit.

Can I combine hiking with other outdoor activities in Taylor Corners?

Absolutely! Taylor Corners is an excellent base for combining hiking with other outdoor pursuits. Squantz Pond State Park offers opportunities for swimming, fishing, kayaking, and picnicking. Ball Pond is also ideal for fishing, kayaking, and paddleboarding in its clear, non-motorized waters, making it a tranquil spot to relax after a hike.

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