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Routes
Gravel rides
United States
Connecticut

Western Connecticut Planning Region

Routes
Gravel rides
United States
Connecticut

Western Connecticut Planning Region

The best gravel rides in Western Connecticut Planning Region

5.0

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145

riders

31

rides

Gravel biking in Western Connecticut Planning Region offers diverse landscapes characterized by rolling hills, tranquil lakes, and extensive forested areas. The region features a network of routes that combine paved roads with unpaved paths, dirt roads, and former rail trails. This varied terrain provides both challenging climbs and more leisurely rides through scenic countryside.

Best gravel bike trails in Western Connecticut Planning Region

  • The most popular gravel bike trail is Cross River reservoir dam – Cross River Reservoir loop from…

Last updated: April 30, 2026

20

riders

#1.

Cross River reservoir dam – Cross River Reservoir loop from Mianus River Gorge Preserve

51.0km

03:38

700m

700m

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

Easy gravel ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Popular around Western Connecticut Planning Region

Gravel biking around Lakeside Woods

Gravel biking around Sherman

Gravel biking around Sail Harbor

Gravel biking around Stamford

Gravel biking in Mianus River State Park Scenic Reserve

Gravel biking around Sandy Hook

Gravel biking around Bogus Hill

Gravel biking in Pootatuck State Forest

Gravel biking around Candlewood Lake Club

Gravel biking around Inglenook

Other adventures in Western Connecticut Planning Region

East Coast Greenway — An unforgettable ride along the Atlantic Seaboard

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Tips from the Community

Andrus
May 9, 2025, The Bedford Oak

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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This well-maintained dirt road is great for biking, especially int he autumn when the fall leaves transform the trail. The road takes you right up to the water with excellent views of the Housatonic River.

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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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Sal J. Prezioso Mountain Lakes Park is Westchester’s northernmost county park and spans 1,082 acres of rugged landscape and native hardwood forest. With five lakes and a stunning overlook, the park is a premier destination for outdoor activities including hiking, camping, and fishing, and ice skating, snow-shoeing, and cross-country skiing in the winter. During summer, the park hosts Camp Morty, offering a traditional camp experience for underprivileged children in Westchester. It is also a popular spot for weddings and other events with a spacious lodge and dining hall. The park is open year-round, from dawn to dusk and leashed dogs are allowed. While a county park pass is not required, camping fees apply. Most of the trails here are for hiking, but the main road (Mountain Lakes Camp Road, which turns into a gravel road named Pine Lake Road) through the park is a popular, challenging climb through this scenic area.

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You can't ride bikes on the trails, but a nice spot for lunch (byo) when rambling in the CT/NY liminal zone. Lock your bike (or drive there) for a short but sweet hike.

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Already climbing from Brookfarm Rd East. Gravel sector maxes at about 10%. Careful on the decent on the other side...

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This is a wonderful, quiet stretch of road. It winds through woodlands, and you will occasionally pass some beautiful houses.

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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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Frequently Asked Questions

How many gravel bike trails are available in the Western Connecticut Planning Region?

There are over 30 gravel bike trails mapped in the Western Connecticut Planning Region on komoot, offering a wide range of experiences from easy scenic rides to challenging multi-hour adventures. The region's diverse landscape, with its rolling hills and forested areas, provides varied terrain for all skill levels.

Are there gravel bike trails suitable for beginners in Western Connecticut?

Yes, beginners can find suitable gravel bike trails. For an easier ride, consider the Old Mine Park – Pequonnock Valley Greenway loop from Botsford. This 16.8-mile route follows the Pequonnock Valley Greenway, offering varied surfaces and scenic river views without significant elevation gain.

Where can I find challenging gravel routes in Western Connecticut?

For advanced riders seeking a challenge, the region offers several difficult routes. The River Trail – Tracy Road Gravel Route loop from New Milford is a demanding 78.5-mile trail with over 5,300 feet of elevation gain. Other challenging options include the 'Redding Rumble' in Fairfield County, known for its significant elevation changes.

Are there any family-friendly gravel bike routes in the area?

While specific family-friendly routes are not detailed in the guide, many multi-use trails and rail trails in the region are suitable for families. The Larkin State Park Trail, for example, is a 10.3-mile linear trail with varying surfaces that follows an old railroad bed, providing a relatively flat and accessible option for a family outing.

What kind of scenery can I expect on gravel bike trails in Western Connecticut?

Gravel biking in Western Connecticut offers a mix of picturesque landscapes. You'll encounter rolling hills, tranquil lakes like Lake Waramaug, scenic rivers such as the Housatonic, and extensive forested areas. Routes often pass through charming small towns and offer views of reservoirs like the Cross River Reservoir.

Are there any trails that feature waterfalls or other natural landmarks?

Yes, the region is home to notable natural features. Kent Falls State Park, for instance, boasts a picturesque 250-foot waterfall with a short trail alongside it, making it a beautiful spot to visit. While not directly on a gravel route, it's a significant landmark in the area. For more natural beauty, explore highlights like the View of Saugatuck Reservoir.

Are there loop gravel bike trails available?

Many gravel routes in Western Connecticut are designed as loops, allowing you to start and end at the same point. Examples include the Housatonic River – Bulls Bridge loop from Wingdale, a 33.9-mile route, and the Cross River Reservoir – Cross River reservoir dam loop from Mianus River Gorge Preserve, which covers 38.2 miles.

What do other gravel bikers enjoy the most about gravel biking in Western Connecticut Planning Region?

The area is highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the diverse terrain, from quiet woodlands to scenic river valleys, and the opportunity to explore charming rural landscapes on routes that combine paved and unpaved sections.

What is the best season for gravel biking in Western Connecticut?

The Western Connecticut Planning Region offers enjoyable gravel biking throughout much of the year. Spring and fall provide pleasant temperatures and beautiful foliage, while summer can be great for early morning or late afternoon rides. Always check local weather conditions, especially for trail conditions after rain or during winter.

Are there any dog-friendly gravel trails in Western Connecticut?

Many state parks and multi-use trails in Western Connecticut allow dogs on leash. For example, the White Memorial Conservation Center permits bicycles and dogs on designated gravel roads and trails. It's always best to check specific park or trail regulations before heading out with your canine companion.

Are there any attractions or points of interest near the gravel trails?

Yes, the region is rich in attractions. You can find beautiful lakes like South Norwalk Reservoir and Squantz Pond State Park. The Connecticut Gold Coast also offers scenic views. Many routes pass through or near charming towns, providing opportunities to explore local shops or grab a bite.

How long do gravel biking routes typically take in this region?

Route durations vary significantly based on distance and difficulty. For example, the Cross River reservoir dam – Cross River Reservoir loop from Mianus River Gorge Preserve, a 31.7-mile difficult trail, typically takes about 3 hours 38 minutes. Shorter, easier routes might take an hour or two, while longer, more challenging ones like the River Trail – Bulls Bridge loop from New Milford (70.1 miles) can take over 8 hours.

Most popular routes in Western Connecticut Planning Region

Hiking in Western Connecticut Planning Region

Most popular attractions in Western Connecticut Planning Region

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Didn’t find what you were looking for?

Check out more Gravel rides throughout Western Connecticut Planning Region below and find the perfect route in your destination.

Paugussett State ForestPootatuck State ForestCandlewood Lake ClubSandy HookShermanInglenookSail HarborStamfordLakeside WoodsMianus River State Park Scenic ReserveBogus Hill

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