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Routes
Hikes
United States
Connecticut

Northwest Hills Planning Region

Routes
Hikes
United States
Connecticut

Northwest Hills Planning Region

The best walks and hikes in Northwest Hills Planning Region

4.6

(102)

1,540

hikers

167

hikes

If you’ve ever tried planning hiking in Northwest Hills Planning Region, you know how quickly the sheer number of trails can feel overwhelming. It’s tough to tell which routes are genuinely worth your time and effort, and which are just filler. That’s where we come in. Our komoot community has walked, ridden, and reviewed these trails, creating a curated shortlist of the very best. We’re here to save you the guesswork and point you straight to the routes that deliver.

Last updated: May 11, 2026

5.0

(1)

37

hikers

#1.

Pine Knob Loop Trail

3.86km

01:20

210m

200m

The Pine Knob Loop Trail offers a dynamic hiking experience, winding through dense forests and over rugged, rocky terrain that keeps things interesting. You'll encounter steep inclines and descents, with…

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Easy

5.0

(2)

38

hikers

Step onto the Little Pond Boardwalk Trail for an easy 1.8-mile (2.9 km) hike that offers a unique perspective on a Connecticut wetland. This 43-minute route, with only 17 feet…

Easy
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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,…

Moderate

5.0

(3)

27

hikers

11.1km

04:06

450m

460m

The Macedonia Ridge Trail offers a dynamic hiking experience through Connecticut's rugged landscape, where you'll navigate a mix of hard rock terrain and serene wooded valleys. This moderate 6.9-mile (11.1…

Moderate

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…

Easy

5.0

(1)

19

hikers

The Burr Pond via Wolcott Trail (Blue Blaze) offers a delightful and accessible hike around the scenic Burr Pond in Torrington, Connecticut. You'll enjoy continuous views of the water as…

Easy

12

hikers

6.27km

01:45

130m

120m

The Whittemore Sanctuary offers a delightful escape into nature, winding through diverse woodlands, past tranquil streams, and alongside picturesque ponds. You'll enjoy expansive natural vistas and may even catch glimpses…

Easy

7

hikers

4.02km

01:22

200m

190m

The Black Rock Trail offers a delightful, easy hike through the forested hills of Black Rock State Park in Connecticut. You'll traverse wooded ledges under a canopy of pine, hemlock,…

Easy

5.0

(2)

7

hikers

The Kent Falls Red and Yellow Loop Trail offers an intimate experience with Connecticut's tallest waterfall, a truly impressive 250-foot cascade. This easy 0.8-mile (1.3 km) loop, with 249 feet…

Easy

5.0

(1)

5

hikers

The Mile of Ledges and Tory Den Trail offers a truly engaging hiking experience, winding through rugged terrain dotted with impressive rock formations and massive boulders. You'll spend much of…

Moderate
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Popular around Northwest Hills Planning Region

Hiking around Terryville

Hiking around Torrington

Hiking around Northwest Harwinton

Hiking around Pleasant Valley

Hiking in American Legion State Forest

Hiking in Peoples State Forest

Hiking around Bridgewater

Hiking around Canaan

Hiking around Oakville

Hiking around Winsted

Other adventures in Northwest Hills Planning Region

The Appalachian Trail — America's most iconic long-distance hike

Hiking Collection by

Jamie S.

Tips from the Community

J.D.
September 28, 2025, Old Mine Preserve

Interesting trails around the site of an old mining operation. Shepaug River views and an active distillery on site!

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Nice Lookout westwards

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0

To reach this point, you'll go through a heavily forested area with several viewpoints along the way. From here, you can enjoy one of these viewpoints, offering a scenic vista of the rolling hills of the Housatonic Meadows State Park.

1

0

Will
December 7, 2023, Burr Pond

This is a great local pond for swimming and picnicking. There are several trails that run parallel to the pond, making it an accessible hiking destination.

0

0

Scott
December 4, 2023, Tory's Den

In the woods of Burlington lies the impressive rock formation known as the "Tory Den," where British sympathizers once hid. This massive rock structure, with nooks, crannies, and a small escape hole, reveals its historical secrets amid blackened walls and rock ledges.

0

0

AverieOutside
December 3, 2023, Little Pond

Little Pond is a stop along the Little Pond Boardwalk Trail through the White Memorial Conservation Area. The area is known as a hot spot for birding and can be a good area for spotting wildlife.

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0

maniboyflex
November 26, 2023, Blackmans Hill

Blackmans Hill is a small forested 930 ft summit in Whittemore Sanctuary and has a bit of a view but is mostly obscured by trees. The hike there is an easy and modest incline, and it is possible to pass the summit on a loop around the Whittemore Sanctuary, which has many different trails crossing the park.

0

0

Can be slippery with leaves and water or ice. Take your time. Easier to climb up than slide down imho

1

0

Frequently Asked Questions

How many hiking trails are available in the Northwest Hills Planning Region?

The Northwest Hills Planning Region offers a wide array of hiking opportunities, with over 75 trails recorded on komoot. These trails cater to various skill levels, from easy walks to more challenging mountain ascents.

What kind of landscapes can I expect to see while hiking in this region?

Hikers in the Northwest Hills Planning Region will encounter diverse landscapes, including rolling hills, significant peaks like Bear Mountain, and expansive forests such as Mount Washington State Forest. The region also features scenic valleys, clear streams, and picturesque water bodies like the Barkhamsted Reservoir, providing a dynamic outdoor experience.

Are there any easy or family-friendly hiking options in the Northwest Hills Planning Region?

Yes, the region offers numerous easy trails suitable for families. For instance, the Little Pond – Little Pond Boardwalk Trail loop from Litchfield Historic District is an easy option, covering just under 3 km. Another gentle choice is the Scenic Nature Pathway loop from New Preston, which is about 6.7 km long.

What do other hikers say about the trails in Northwest Hills Planning Region?

The trails in the Northwest Hills Planning Region are highly regarded by the komoot community, holding an average rating of 4.7 stars from over 45 reviews. Hikers frequently praise the well-maintained paths, the serene forest environments, and the rewarding views from higher elevations.

Are there any notable landmarks or natural features to look out for along the trails?

Yes, the region is rich with natural and historical landmarks. Hikers can explore features like Bear Mountain (2,320 feet), the highest peak in Connecticut, or visit scenic water bodies such as Lake Waramaug State Park and Little Pond. Other points of interest include the historic Bulls Bridge and the unique Steep Rock Tunnel.

Can I find trails with waterfalls in the Northwest Hills Planning Region?

Yes, the region features picturesque water features, including hidden waterfalls. Enders Brook Falls in Peoples State Forest is a notable example, enhancing the hiking experience with its natural beauty.

Are there any circular hiking routes available?

Many trails in the Northwest Hills Planning Region are designed as loops, offering varied scenery without retracing your steps. An example is the Bear Mountain (2,320 feet) – Sage's Ravine loop from Salisbury, which takes you through mountainous terrain and ravines.

What is the best time of year to go hiking in the Northwest Hills Planning Region?

The Northwest Hills Planning Region offers beautiful hiking experiences throughout the year. Spring brings lush greenery and blooming wildflowers, while autumn is particularly stunning with vibrant fall foliage. Summer provides shaded trails in the extensive forests, and winter offers opportunities for snowshoeing or quiet walks, though some trails may be more challenging.

Is there public transport or parking available near the trailheads?

While specific public transport options to all trailheads may be limited, many popular hiking areas in the Northwest Hills Planning Region, such as state parks and forests, typically offer designated parking facilities. It's advisable to check specific trail information for parking details before your visit.

Are there any trails that are part of the Appalachian Trail in this region?

Yes, a significant portion of the Appalachian Trail, approximately 47 miles, traverses the Northwest Hills Planning Region. This offers hikers the chance to experience a world-renowned long-distance trail within the local landscape.

What is the general difficulty level of hikes in the Northwest Hills Planning Region?

The region offers a good mix of difficulties. Out of 77 recorded tours, 35 are rated as easy, 36 as moderate, and 6 as difficult. This variety ensures that hikers of all experience levels can find suitable routes, from gentle strolls to challenging ascents with significant elevation changes.

Where can I find more detailed maps or information about the trails?

The Northwest Hills Council of Governments (NHCOG) has developed an interactive trails map for the region, which can be a useful resource for finding trails based on location, distance, difficulty, and allowed uses. You can also find more information on the Housatonic Heritage website.

Most popular routes in Northwest Hills Planning Region

Easy hikes in Northwest Hills Planning Region

Most popular attractions in Northwest Hills Planning Region

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Didn’t find what you were looking for?

Check out more Hikes throughout Northwest Hills Planning Region below and find the perfect route in your destination.

Pleasant ValleyAlgonquin State ForestNepaug State ForestGreat Mountain ForestMount Tom State ParkMacedonia Brook State ParkBurr Pond State ParkChimney PointRivertonThomastonPeoples State ForestMount Bushnell State Park Scenic ReserveCampbell Falls State Park ReserveSunny Brook State ParkPaugnut State ForestMattatuck State ForestAmerican Legion State ForestWoodbury CenterNew Hartford CenterFalls VillageWatertownStillwater Pond State ParkCornwallSharonPlatt Hill State ParkWyantenock State ForestLake Winfield Recreation AreaBethlehem VillageJohn A. Minetto State ParkHumaston Brook State ParkOakvilleNew PrestonNew MilfordCamp Columbia State ParkBantamLakevilleDennis Hill State ParkWest CornwallGaylordsvilleNorfolkAlgonquin State Forest, Kitchel PreserveHousatonic State Forest, Gold'S Pines BlockBridgewaterCanaanLake Waramaug State ParkTorringtonWinstedTerryvilleCornwall BridgeNorthwest HarwintonMount Riga State ParkLitchfieldBridgewater Recreation AreaAbove All State ParkHaystack Mountain State ParkLovers Leap State Park

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