4.8
(21)
263
hikers
29
hikes
Hiking around New Milford explores the varied landscapes of Litchfield County, characterized by the Housatonic River, rolling hills, and extensive forests. The terrain includes moderate hills, steep ridges, and valleys, offering diverse hiking experiences. This mix of natural features provides a range of hiking options, from gentle river walks to more moderate routes with elevation gain. The region features significant natural landmarks such as the Housatonic River Valley, Candlewood Mountain, and Lake Lillinonah.
Last updated: July 9, 2026
4.7
(3)
28
hikers
8.09km
02:17
180m
120m
The Steep Rock Loop offers a captivating journey through varied landscapes, starting with a gentle stroll alongside the tranquil Shepaug River. You'll soon find yourself ascending through peaceful pine woods, eventually reaching the Steep Rock Summit for expansive views over the "Clamshell" section of the valley. This moderate 5.0-mile (8.1 km) hike, with its 604 feet (184 metres) of elevation gain, provides a rich experience of Connecticut's natural beauty, typically taking about 2 hours and 16 minutes to complete.
Planning your visit to the Steep Rock Loop is straightforward, as it's a popular destination throughout the year, particularly during the scenic spring and autumn months. While specific parking information isn't detailed, arriving early is always a good strategy to ensure a spot at the trailhead. No permits or special access requirements are noted, making this a convenient and welcoming trail for spontaneous adventures.
What truly sets the Steep Rock Loop apart are its unique historical features, seamlessly integrated into the natural environment. You'll have the chance to walk through a hand-built 235-foot Historic Railroad Tunnel, cross a charming Suspension Bridge over the Shepaug River, and explore the ruins of the old Holiday House. These landmarks, combined with the panoramic vistas from Steep Rock Summit, offer a compelling blend of history and scenery that makes this route a standout among Steep Rock Preserve hiking routes.
4.6
(5)
24
hikers
5.60km
01:38
150m
150m
The Roxbury Mines trail offers a distinctive blend of natural beauty and historical intrigue as you wander through dense woodlands and past striking granite cliffs. You'll discover abandoned quarries and a small pond, with the path occasionally following old dirt roads. The varied terrain keeps things interesting, providing a dynamic experience for hikers of all levels.
Planning your visit to the Mine Hill Preserve is straightforward; the trail system is well-maintained and generally accessible. While the route is rated easy, you'll want sturdy hiking boots for the rocky sections. Aim for an earlier start to enjoy the peaceful atmosphere and ensure ample time to explore the historical points of interest along the way.
What truly sets Roxbury Mines apart is its rich past as a 19th-century iron-making complex, now a National Historic Landmark. As you hike the 3.5-mile (5.6 km) loop, which involves about 503 feet (153 metres) of climbing and takes roughly 1 hours and 38 minutes, you'll encounter fascinating remnants like blast furnaces and mine tunnels. These tunnels also serve as vital bat hibernacula, adding an ecological layer to this unique historical journey.

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3
hikers
1.93km
00:31
20m
20m
The New Milford Reservoir Loop offers a delightful and accessible escape into nature, winding through pleasant wooded areas with continuous picturesque water views of the reservoir. You'll encounter charming old stone walls and a mix of natural, unpaved surfaces, with boardwalks and bridges making for easy passage over any damp spots. It's a truly easy 1.2-mile (1.9 km) hike, perfect for a quick refresh.
This trail is consistently described as easy, with a minimal 71 feet (22 metres) of elevation gain, making it suitable for nearly all fitness levels. You can comfortably complete the loop in about 30 minutes, making it an ideal choice for a casual stroll, a family outing, or a quick dog walk. Parking is generally available at the trailhead, and it's a popular spot for a convenient outdoor escape.
What makes the New Milford Reservoir Loop stand out is its combination of gentle terrain, scenic beauty, and short distance, making it a favorite for those seeking a quick dose of nature in New Milford, Connecticut. It's particularly notable for its accessibility and dog-friendly policy, offering a peaceful natural setting right within the town.
1
hikers
2.79km
00:46
50m
50m
The Lillinonah Loop offers a delightful, easy hike through classic New England woodlands, providing picturesque views of Lake Lillinonah and the Housatonic River. You'll wander through diverse terrain, from soft forest paths to occasional rocky sections, all while enjoying the serene atmosphere. The route is a short 1.7 miles (2.8 km) with a modest 165 feet (50 metres) of elevation gain, making it an ideal choice for a quick, scenic escape that takes around 46 minutes to complete.
Planning your visit is simple, with convenient parking options available off Echo Valley Road and Hanover Road. While the trail is generally accessible, it's worth noting that some areas have historically seen temporary closures to protect nesting bald eagles, particularly in the spring. For a peaceful experience, aim to start your hike earlier in the morning or later in the afternoon to avoid any potential crowds.
Beyond the natural beauty, the Lillinonah Loop is rich with interesting features, including remnants of old stone walls that speak to the area's history. You might also observe active maple sugaring operations near the Echo Valley Road parking lot, with their distinctive blue tubes collecting sap. The trail's designation as a "scenic trail" by the Connecticut Department of Environment Protection highlights its unique charm and natural appeal.
9.98km
02:34
50m
50m
Hike the moderate 6.2-mile Housatonic River Trail, enjoying river views and diverse wildlife over 162 feet of elevation gain.
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Interesting trails around the site of an old mining operation. Shepaug River views and an active distillery on site!
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This well-maintained dirt road is great for biking, especially int he autumn when the fall leaves transform the trail. The road takes you right up to the water with excellent views of the Housatonic River.
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Yes, the region has several great options for families. The Still River Greenway is a very accessible choice, offering a relatively flat path along the river. Another excellent option is the Squantz Pond State Park loop, which provides a gentle walk with lovely water views.
Many trails in the area are dog-friendly, but it's always best to check the specific regulations for each park. Lover's Leap State Park and Hidden Valley Preserve are known to be popular spots for people hiking with their dogs. Please keep your dog on a leash and clean up after them to help keep the trails enjoyable for everyone.
Locals and visitors enjoy a variety of spots. Lover's Leap State Park is a highly regarded favorite, known for its historic bridge and scenic river views. For a quieter experience with well-maintained trails through woodlands, Hidden Valley Preserve is an excellent choice. The New Milford River Trail offers a pleasant, accessible walk right along the Housatonic River.
Absolutely. For dramatic views over the Housatonic River gorge, the trails at Lover's Leap State Park leading to the main rock formation are a must-see. For a more challenging hike with rewarding vistas, the Housatonic Range Trail on Candlewood Mountain offers several scenic overlooks of the river valley, including at 'Suicide Ledges'.
Hiking is possible year-round, but autumn is particularly spectacular when the fall foliage is at its peak, creating stunning landscapes. Spring offers pleasant temperatures and blooming wildflowers, while summer is great for enjoying the lush green forests, though it can be humid. Winter hiking can be beautiful, but be prepared for snow and ice on the trails.
Yes, for those seeking a more strenuous trek, the Housatonic Range Trail provides a rugged 6.2-mile path along Candlewood Mountain. It features significant elevation changes and unique rock formations like the 'Corkscrew'. The trails at Sunny Valley Preserve, particularly the one up Wolf Pit Mountain, also offer a more challenging hike with rewarding seasonal views.
Yes, several trails explore the region's past. The Mine Hill Preserve – Quarry Bridge loop from Roxbury is a fantastic choice, taking you past the well-preserved ruins of a 19th-century quarry and iron furnace. Lover's Leap State Park also contains the ruins of the old Silex factory and the Hurd estate, adding a historical element to your hike.
While the area is better known for its river views and rolling hills than for large waterfalls, you can find smaller cascades and beautiful water features. The trails in Hidden Valley Preserve follow the Shepaug River and feature lovely rapids and small drops, especially after rainfall. The brooks and streams within Sunny Valley Preserve also create scenic water features along the paths.
There are over 10 designated hiking routes in the immediate New Milford area available on komoot. These range from easy riverside greenways to moderate woodland loops, offering plenty of options to explore the Litchfield County landscape.
The trails around New Milford are highly rated by the komoot community, with an average score of 4.8 stars. Hikers often praise the region's beautiful riverside scenery, the well-maintained paths through quiet woodlands, and the interesting mix of natural beauty and local history.
Yes, many of the best hikes in the area are loops, allowing you to enjoy a varied journey without retracing your steps. The Williams Park loop is a great example of an easy circular walk. For a more moderate option, the Rock tunnel loop from Washington offers a varied circuit through the woods.
Most local preserves and trails, such as Sunny Valley Preserve and the New Milford River Trail, offer free access and parking. However, some state parks like Lover's Leap State Park may charge a parking or entrance fee, particularly during the peak season (weekends and holidays). It's always a good idea to check the specific park's website for the most current fee information before you go.


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