The best walks and hikes around New Milford
4.8
(20)
259
hikers
30
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.
Best hiking trails around New Milford
- The most popular hiking route is Steep Rock Loop, a 5.0 miles (8.1 km) trail that takes 2 hours 17 minutes to complete. This moderate hike features a mix of woodland paths and some elevation change, including views of the Shepaug River.
- Another top favourite among local hikers is Roxbury Mines, an easy 3.5 miles (5.6 km) path. This route explores a historic preserve, passing by old quarry and furnace ruins.
- Local hikers also love the Housatonic River Trail, a 6.2 miles (10.0 km) trail leading through riverside scenery, often completed in about 2 hours 34 minutes.
- Hiking around New Milford is defined by riverside paths, dense woodlands, and rolling hills. The trail network offers accessible options for different ability levels, from level greenways to routes with more varied terrain.
- The routes in New Milford are highly rated by the komoot community with an average score of 4.8 stars from more than 20 reviews. More than 250 hikers have used komoot to explore New Milford's varied terrain.
Last updated: May 13, 2026
4.7
(3)
27
hikers
8.09km
02:17
180m
120m
Embark on the Steep Rock Loop, a moderate hiking route that guides you through varied landscapes and offers rewarding views. You will follow the tranquil Shepaug River, enjoying serene waterside scenery before the trail ascends through dense pine woods. This 5.0-mile (8.1 km) journey involves a climb of 604 feet (184 metres) and typically takes around 2 hours and 16 minutes to complete.
To begin your hike, head to the Steep Rock Preserve in Washington, Connecticut. Parking is usually available directly at the trailhead, making access straightforward for visitors. Be aware that the final 0.4 miles to the summit can be quite steep, so plan your energy accordingly. This trail is a great option for a half-day outing when you are looking for a solid workout with scenic rewards.
The route is known for blending natural beauty with historical elements. As you hike, you will reach the Steep Rock Summit, which provides panoramic views over the Clamshell section of the Shepaug River Valley. The trail also features unique points of interest, including a historic railroad tunnel and a picturesque suspension bridge, adding layers of discovery to your outdoor experience.
4.6
(5)
23
hikers
5.60km
01:38
150m
150m
Embark on an easy hike through the Roxbury Mines, a 3.5-mile (5.6 km) route that takes approximately 1 hour and 38 minutes to complete. You'll gain 503 feet (153 metres) in elevation as you explore scenic woodlands and a diverse landscape. The trail offers a unique blend of natural beauty, featuring rocky outcroppings and views of the Shepaug River, alongside fascinating historical remnants. Keep an eye out for the old roasting ovens and abandoned quarries that dot the path, providing a glimpse into the area's past.
Planning your visit to Roxbury Mines is straightforward. The trail is generally well-maintained and clearly marked, making navigation simple for hikers of all experience levels. You can typically find parking available at the Mine Hill Preserve, which serves as the trailhead. While the route is considered easy, some sections might have loose rocks, so wearing sturdy hiking boots is a good idea to ensure a comfortable and safe journey.
This trail is notable for its rich history, as the Mine Hill Preserve is a National Historic Landmark. As you hike, you'll encounter remnants of a 19th-century iron-making complex, including a blast furnace, which adds a unique historical dimension to your outdoor adventure. The varied terrain, combining natural features with these historical sites, makes Roxbury Mines a distinctive and engaging experience in the region.
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3
hikers
1.93km
00:31
20m
20m
Enjoy an easy 1.2-mile hike around the New Milford Reservoir, offering scenic water views and charming old stone walls in just 30 minutes.
1
hikers
2.79km
00:46
50m
50m
Hike the easy 1.7-mile Lillinonah Loop in Sunny Valley Preserve, offering scenic views of Lake Lillinonah and diverse forest terrain.
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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Tips from the Community
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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Frequently Asked Questions
Are there any easy, family-friendly hikes in the New Milford area?
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.
Can I bring my dog on the hiking trails near New Milford?
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.
What are some popular places to hike around New Milford?
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.
Are there any trails with scenic viewpoints or overlooks?
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'.
What is the best time of year to hike in the New Milford region?
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.
Are there any challenging hikes available near New Milford?
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.
I'm interested in history. Are there any hikes that feature historic ruins?
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.
Do any of the hiking trails have waterfalls?
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.
How many hiking trails are there around New Milford?
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.
What do other hikers think of the trails in New Milford?
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.
Are there any circular or loop hikes available?
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.
Are there fees for parking or entering the parks?
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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