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United States
Connecticut
Western Connecticut Planning Region

Riverside

The best road cycling routes around Riverside

4.5

(40)

1,500

riders

157

rides

Road cycling around Riverside features a landscape characterized by a network of reservoirs, lakes, and greenways. The terrain includes rolling hills and some flatter sections, offering varied elevation profiles for road cyclists. Routes often incorporate scenic water views and established park paths. The region provides a mix of natural and developed areas suitable for cycling.

Best road cycling routes around Riverside

  • The most popular road cycling route is Taconic Road – View of Rockwood Lake loop from Riverside, a…

Last updated: October 18, 2026

5.0

(1)

83

riders

#1.

Taconic Road – Putnam Lake loop from Cos Cob

58.0km

02:34

490m

490m

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

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Moderate

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

Moderate
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Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard

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

Moderate

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

Moderate
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Popular around Riverside

Hiking around Riverside

Cycling around Riverside

Running Trails around Riverside

Tips from the Community

Andrus
May 9, 2025, Grant Road

Great stretch of a well paved and quiet road. There is little to no shoulder though, so that might put off les experienced riders.

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The Bedford Oak is one of those rare living landmarks that quietly connects the past to the present. Estimated to be over 500 years old, this massive white oak has stood through centuries of change in Bedford, from Native American times to the Revolutionary War and beyond. Locals have always held it in high regard, and when development threatened its space in the 1970s, the community stepped up to save it. Thanks to their efforts, the tree and the land around it are now protected and cared for.

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The park is situated in a small valley that offers a steady climb up the road no matter which direction you choose.

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mtm05005
February 26, 2024, Cross River Bridge

As you pass over Cross River Bridge, you get a great view of the water below. The traffic is normally light, so you should be able to go slowly to enjoy the view. There is no shoulder on the road as it crosses the river, so it is not safe to stop while on the bridge.

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mtm05005
February 20, 2024, Brown Preserve

Brown Preserve is a beautiful, protected woodland that Stanwich Road runs through. It is a great section of shady road to ride through, especially on a hot summer's day.

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Jamie S.
February 19, 2024, Reservation Road

This lovely smooth, paved road goes through Ward Pound Ridge Reservation over rolling hills. This is an especially pretty road to ride in the fall as the leaves change from green to orange, yellow, and red.

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Alex
February 1, 2024, Taconic Road

The views from this fast flowing and good quality road are lovely. With trees and quiet fields around you will gain a feeling of inner peace cycling along it.

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Cross River Reservoir is a freshwater lake in scenic Westchester County. It is in a gorgeous forest setting, and when you cycle past it here on the Old Post Road Bridge, the views are simply stunning. As you look out over both sides of the bridge, there is nothing but tranquil water and a tree-lined shoreline. In the fall, the colors are stunning!

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Frequently Asked Questions

How many road cycling routes are available around Riverside?

There are over 10 road cycling routes around Riverside, offering a variety of experiences for different skill levels. The komoot community has explored 14 distinct routes in the area.

Are there easy road cycling routes suitable for beginners or families in Riverside?

Yes, Riverside offers several easy road cycling routes. For instance, the Binney Park – East Coast Greenway loop from Cos Cob is a relatively flat 9.0-mile (14.5 km) trail that takes about 39 minutes to complete, ideal for a relaxed ride. Another option is the East Coast Greenway – Binney Park loop from Riverside, which is 34.7 miles (55.9 km) and also considered easy.

Where can I find road cycling routes with significant elevation gain around Riverside?

For those seeking more challenging rides with elevation gain, Riverside's terrain includes rolling hills. Routes like the View of Rockwood Lake – Cross River Reservoir loop from Riverside feature significant climbs, with over 2,400 feet (745 m) of elevation gain over 52.5 miles (84.5 km). This route is rated as moderate due to its length and elevation.

What kind of scenery can I expect on road cycling routes in Riverside?

Road cycling routes around Riverside are characterized by scenic water views, including reservoirs and lakes, and established park paths. You'll often encounter a mix of natural and developed areas, with routes winding through greenways and offering glimpses of the region's varied landscape.

Are there any notable landmarks or attractions along the road cycling routes?

Yes, several routes pass by interesting landmarks and natural attractions. For example, the View of Rockwood Lake – St Mary's Church loop from Riverside offers views of Rockwood Lake and passes by St Mary's Church. You might also encounter sections of the East Coast Greenway, or pass near Greenwich Point Beach and Mianus River Natural Park on various routes.

What do other road cyclists enjoy most about road cycling in Riverside?

The road cycling experience in Riverside is highly rated by the komoot community, with an average score of 4.6 stars from over 25 reviews. Cyclists often praise the varied terrain, which includes reservoir loops, greenway paths, and rolling hills, providing options for different ability levels and scenic views.

Are there any loop trails for road cycling in Riverside?

Many of the road cycling routes in Riverside are designed as loops, allowing you to start and end at the same point. Examples include the popular View of Rockwood Lake – Cross River Reservoir loop from Riverside and the View of Rockwood Lake – St Mary's Church loop from Riverside, both offering circular journeys through the region.

What is the typical length of road cycling routes around Riverside?

The length of road cycling routes around Riverside varies significantly. You can find shorter routes like the Binney Park – East Coast Greenway loop from Cos Cob at 9.0 miles (14.5 km), up to longer, more challenging rides such as the View of Rockwood Lake – Cross River Reservoir loop from Riverside, which spans 52.5 miles (84.5 km).

Are there less crowded road cycling options in Riverside?

While some popular routes can see more traffic, exploring the full range of routes on komoot can help you find less crowded options. Routes that venture further from central areas or those with more significant elevation might offer a quieter experience. The region's network of greenways and reservoir loops provides ample space to explore.

What are some moderate road cycling routes in Riverside?

Riverside features several moderate road cycling routes that balance distance and elevation. The View of Rockwood Lake – St Mary's Church loop from Riverside is a moderate 34.6-mile (55.7 km) path with over 1,700 feet (528 m) of elevation gain. Another moderate option is the Taconic Road – Mianus River Reservoir loop from North Mianus, covering 21.9 miles (35.3 km) with over 1,100 feet (360 m) of ascent.

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