4.5
(85)
2,095
riders
197
rides
Road cycling routes in Northwest Hills Planning Region traverse a diverse landscape characterized by rolling hills, dense forests, and scenic valleys. The region features varied topography, from gently rolling terrain to more challenging mountainous areas with significant elevation gains. Numerous lakes and rivers, including Lake Waramaug and the Housatonic River, provide picturesque backdrops for rides. This combination of natural features offers road cyclists a range of experiences, from leisurely spins to routes with serious climbs.
Last updated: April 24, 2026
58.0km
02:50
660m
660m
This 36.0-mile road cycling loop from Barkhamsted to Simsbury offers a moderate challenge with 2180 feet of elevation gain.
61
riders
19.9km
01:00
310m
310m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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2.0
(1)
35
riders
29.9km
01:36
180m
180m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
22
riders
50.4km
02:34
740m
740m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
21
riders
38.1km
01:47
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
17
riders
110km
05:10
1,330m
1,330m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
12
riders
48.0km
02:14
480m
480m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
12
riders
52.8km
02:27
580m
580m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
12
riders
29.0km
01:31
340m
340m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
6
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Northwest Hills Planning Region
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The Farmington River winds through the hills and valleys of northwestern Connecticut, offering a mix of serene landscapes and lively rapids. Known for its clear waters and rich history, the river has long been a favorite for kayaking, fly fishing, and tubing. It flows through quaint towns and dense woodlands, providing both a habitat for wildlife and a peaceful retreat for locals and visitors alike. With its roots in glacial melt and centuries of human use, the Farmington tells a quiet but powerful story of nature and community.
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This is a tiny but highly scenic little park. The roads that circumnavigate Lake Warmaug are partially shaded and go right up to the water's edge, and the views out across the water are especially beautiful in the autumn. There is also camping, hiking, and kayaking here, as well as a couple small beaches for swimming.
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The Naugatuck River, spanning 40.2 miles in Connecticut, flows through the Naugatuck River Valley southward, eventually joining with the Housatonic River at Derby before reaching Long Island Sound. From the bridge on Main Street, there are nice views of the river with rolling hills in the background.
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The Downtown Torrington Historic District is in the central downtown area. This area spans 56 acres, and has architecture from the mid-19th to early 20th centuries. Listed on the National Register of Historic Places in 1988, the main street offers a unique setting for biking, where visitors can admire the well-maintained old buildings and experience a journey through time.
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While biking around downtown Torrington, the Warner Theatre is a standout monument. It is a historic performing arts venue that has been an important part of the community since its opening in 1931. The interior is in Art Deco style, and over the years, it has evolved into a cultural hub, hosting everything from Broadway shows and concerts to dance recitals and film screenings.
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Stillwater Pond State Park, spanning 226 acres, is on the West Branch Naugatuck River. The pond is a great place to go fishing and boating and features a paved boat ramp. It's known for its gorgeous fall foliage, with the best views around mid-October.
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The Amos Baldwin House is a historic colonial house built around 1765. While riding by this area, take a peek from the street. It is one of the community's oldest and most important examples of colonial architecture. Recognized for its historical importance, the house was added to the National Register of Historic Places in 2016.
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Topsmead State Forest was once the summer house of Edith Morton Chase, first president of the Chase Brass and Copper Company. When she died in 1972, she left her land to the state. Today, the home, built in the late 1920s, is officially on the National Register of Historic Places.
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The Northwest Hills Planning Region offers a wide selection of road cycling routes, with over 190 routes available. These routes cater to various skill levels, from easy spins to challenging climbs.
Yes, the region features 15 easy road cycling routes perfect for beginners or those seeking a more relaxed ride. A great option is the Lake Waramaug State Park – Lake Waramaug loop from Marbledale, which is 12.4 miles (19.9 km) and takes about 53 minutes to complete, offering scenic lakefront views.
For experienced cyclists looking for a challenge, there are 23 difficult routes available. Consider the Topsmead State Forest – Amazing descent loop from Torrington, a demanding 111 km route with significant elevation gain, or the Stillwater Pond State Park – Naugatuck River loop from Torrington, which spans over 83 km and includes nearly 1000 meters of climbing.
Absolutely. The region is known for its beautiful lakes and rivers. Many routes, like the Lake Waramaug – Lake Waramaug State Park loop from Washington, circle picturesque water bodies such as Lake Waramaug. The Housatonic River also parallels many scenic routes, offering stunning views.
Road cycling in this region offers diverse scenery, from gently rolling hills and expansive forests to charming small towns and farmlands. You'll encounter picturesque valleys, historic architecture, and vibrant fall foliage if you visit in autumn. Routes often provide views of significant peaks like Bear Mountain (2,320 feet).
The area is highly rated by the komoot community, with an average score of 4.2 stars from over 10 reviews. Cyclists often praise the varied topography, from serene lake loops to routes with serious climbs, and the beautiful, often quiet, rural roads that wind through dense forests and past charming towns.
Yes, the region is dotted with interesting landmarks. You might pass by the historic Bulls Bridge, the impressive Seville Dam, or cycle near Lake Waramaug State Park. The region's charming towns like Litchfield, Kent, and Cornwall Bridge also offer pleasant stops.
Loop trails are a popular feature for road cycling in the region, allowing you to start and end in the same location. Many routes, such as the Barkhamsted to Simsbury loop or the Rudd Pond – Rail trail bridge loop from Centennial Watershed State Forest, are designed as loops, offering a complete cycling experience without retracing your path.
The Northwest Hills Planning Region is particularly stunning during the fall foliage season, when the countryside transforms into a vibrant tapestry of colors, making for incredibly scenic rides. Spring and summer also offer pleasant conditions with lush greenery, though summer can be warmer. The region's varied terrain is enjoyable across multiple seasons.
Many road cycling routes in the Northwest Hills Planning Region connect or pass through quaint villages and historic towns like Litchfield, Kent, and Cornwall Bridge. These towns often feature historic architecture and town greens, providing excellent opportunities for a break or to explore local charm. The Candy-O's Candy & Collectibles loop from Benton Hill Preserve is an example of a route that offers a mix of natural beauty and local points of interest.
Yes, the Northwest Hills Planning Region is characterized by its varied topography. You'll find routes that combine gently rolling sections with more challenging ascents. For instance, the Seville Dam – Booth Hill loop from New Hartford offers a moderate challenge with significant elevation changes, providing a dynamic riding experience.
The entire region is renowned for its scenic beauty. Routes around Lake Waramaug, such as the Lake Waramaug – Lake Warmaug State Park loop from Lake Waramaug State Park, offer continuous picturesque lake views. Additionally, many routes wind through heavily forested areas and along river valleys, providing stunning natural vistas, especially during the fall.


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