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Routes
Road cycling routes
United States
Connecticut

Northwest Hills Planning Region

The best road cycling routes in Northwest Hills Planning Region

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.

Best road cycling routes in…

Last updated: April 24, 2026

#1.

Barkhamsted to Simsbury loop

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.

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Moderate

61

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Popular around Northwest Hills Planning Region

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Hiking Collection by

Jamie S.

Tips from the Community

oliviakellis
May 18, 2025, Farmington River

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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Alex
February 27, 2024, Naugatuck River

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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Alex
February 27, 2024, The Warner Theatre

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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Alex
February 27, 2024, Amos Baldwin House

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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Alex
February 25, 2024, Topsmead State Forest

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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Frequently Asked Questions

How many road cycling routes are available in the Northwest Hills Planning Region?

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.

Are there easy road cycling routes suitable for beginners in the Northwest Hills Planning Region?

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.

Where can I find more challenging or long-distance road cycling routes in the Northwest Hills Planning Region?

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.

Are there road cycling routes that feature lakes or rivers in the Northwest Hills Planning Region?

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.

What kind of scenery can I expect on road cycling routes in the Northwest Hills Planning Region?

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).

What do other road cyclists enjoy most about road cycling in the Northwest Hills Planning Region?

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.

Are there any specific landmarks or attractions I can see along road cycling routes?

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.

Are there many loop trails for road cycling in the Northwest Hills Planning Region?

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.

What is the best time of year for road biking in the Northwest Hills Planning Region?

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.

Are there road cycling routes that pass through or near charming towns?

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.

Can I find routes that offer a mix of terrain, from flat sections to hills?

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.

Are there any routes that are particularly known for their scenic beauty or viewpoints?

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.

Most popular routes in Northwest Hills Planning Region

Hiking 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 Road cycling routes 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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