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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

4.7

(106)

1,627

hikers

175

hikes

Hiking in Northwest Hills Planning Region, located in Connecticut's Litchfield Hills, features an extensive network of trails across diverse landscapes. The region is characterized by rolling hills, significant peaks such as Bear Mountain, and expansive forests including Mount Washington State Forest. Hikers can explore scenic valleys, discover water features like the Barkhamsted Reservoir and Housatonic River, and traverse varied topography that includes both challenging climbs and gentler paths.

Best hiking trails in Northwest Hills Planning Region

  • The most popular hiking…

Last updated: April 26, 2026

5.0

(1)

37

hikers

#1.

Pine Knob Loop Trail

3.86km

01:20

210m

200m

Discover the Pine Knob Loop Trail, an easy hike that winds through forests of white pines and scrub oak. As you hike, you'll encounter rock ledges and the peaceful Hatch…

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Easy

5.0

(2)

38

hikers

Embark on an easy hike along the Little Pond Boardwalk Trail, a gentle route spanning 1.8 miles (2.9 km) with a minimal elevation gain of just 17 feet (5 metres).…

Easy
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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…

Moderate

5.0

(2)

27

hikers

11.1km

04:06

450m

460m

Embark on the Macedonia Ridge Trail for a moderate hiking challenge spanning 6.9 miles (11.1 km) with a significant elevation gain of 1491 feet (454 metres). This route, estimated to…

Moderate

4.6

(5)

24

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)…

Easy

5.0

(1)

19

hikers

Embark on an easy hike around Burr Pond via the Wolcott Trail (Blue Blaze), a pleasant loop covering 2.6 miles (4.2 km). You'll experience continuous scenic views of the 85-acre…

Easy

11

hikers

6.27km

01:45

130m

120m

Explore the Whittemore Sanctuary on an easy 3.9-mile (6.3 km) hike, designed to take you about 1 hour and 45 minutes. This route offers a gentle ascent of 418 feet…

Easy

6

hikers

4.02km

01:22

200m

190m

Embark on an easy hiking adventure along the Black Rock Trail, a route that guides you through the serene natural landscape of Black Rock State Park. This journey spans 2.5…

Easy

5.0

(2)

7

hikers

Embark on an easy hike along the Kent Falls Red and Yellow Loop Trail, a short 0.8 miles (1.3 km) route that takes about 27 minutes to complete. You will…

Easy

5.0

(1)

5

hikers

Embark on the Mile of Ledges and Tory Den Trail, a moderate hiking route spanning 4.4 miles (7.1 km) with an elevation gain of 357 feet (109 metres). You can…

Moderate
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Popular around Northwest Hills Planning Region

Hiking around Torrington

Hiking around Northwest Harwinton

Hiking around Pleasant Valley

Hiking in Nepaug State Forest

Hiking in American Legion State Forest

Hiking in Peoples State Forest

Hiking around Bridgewater

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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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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

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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.

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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.

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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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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.

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

1

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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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