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Road cycling routes
United States
Connecticut
Western Connecticut Planning Region

Inglenook

The best road cycling routes around Inglenook

4.5

(2)

148

riders

20

rides

Road cycling around Inglenook features a landscape characterized by numerous lakes and a series of rolling to steep hills. The terrain includes varied elevations, offering challenging climbs and descents across its network of roads. This region provides a mix of moderate and difficult road cycling routes, often looping around natural water bodies and through hilly areas.

Best road cycling routes around Inglenook

  • The most popular road cycling route is Maybrook Trailway – Whaley Lake loop from Putnam Lake, a…

Last updated: October 29, 2026

8

riders

#1.

Squantz Pond – Squantz Pond loop from Candlewood Mountain

56.5km

02:50

790m

790m

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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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

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

Hard
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Tips from the Community

Zachary
September 3, 2024, Lake Waramaug State Park

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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Matthew
February 20, 2024, Disbrow Pond

Disbrow Pond is a small body of water just off the side of Sawmill Road. You get a pretty great view from the bridge crossing over the water, but you can hop off the bike and go down next to the water if you pull into the entrance on the north side of the reservoir.

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Jamie S.
February 20, 2024, Squantz Pond

Squantz Pond is a 288-acre lake in Fairfield County, Connecticut on the town line of Sherman and New Fairfield. As you ride on CT-39, you get fantastic views over this large body of water.

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Jamie S.
February 14, 2024, Squantz Pond

Squantz Pond is a 288-acre lake in Fairfield County, Connecticut on the town line of Sherman and New Fairfield. As you ride on CT-39, you get fantastic views over this large body of water.

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This small lake-side park comes equipped with picnic benches and plenty of trees to provide shade on a summers day. A great spot to take a break.

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This is one of three old covered wooden bridges spanning over the Housatonic River. While the one at Cornwall is still intact, the original Old Covered Bridge in Sheffield was destroyed by fire and had to be rebuilt.

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Opportunity to have a decent meal along this route. Friendly folks refill water and it has a proper washroom as well. In general Kent is a good stop to refill or rest before heading further as supply station might become sparse.

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Cemetery at the beginning of the decent. Watch out, there is a sharp turn in the middle of the segment.

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Frequently Asked Questions

What kind of terrain can I expect when road cycling around Inglenook?

Road cycling around Inglenook is characterized by a landscape with numerous lakes and a series of rolling to steep hills. You'll encounter varied elevations, offering a mix of challenging climbs and descents across its network of roads, often looping around natural water bodies and through hilly areas.

How many road cycling routes are available in the Inglenook area?

There are 18 road cycling routes available around Inglenook. These routes offer a range of difficulties, from moderate to difficult, ensuring options for different ability levels.

Are there any easy road cycling routes for beginners or families in Inglenook?

Yes, Inglenook offers 2 easy road cycling routes, which are suitable for beginners or those looking for a more relaxed ride. These routes provide a gentle introduction to the area's scenic beauty without overly challenging terrain.

What are some of the more challenging road cycling routes in Inglenook?

For experienced cyclists seeking a challenge, Inglenook features 3 difficult road cycling routes. One notable option is the Lake Warmaug State Park – Lake Waramaug loop from New Milford, which covers 55.6 miles with over 5,300 feet of elevation gain.

What attractions or natural features can I see along the road cycling routes in Inglenook?

While cycling around Inglenook, you can explore several natural attractions. Highlights include Squantz Pond State Park and Squantz Pond itself, offering scenic lake views. You might also encounter the River Trail and the tranquil Harrybrooke Park.

What do other road cyclists think about the routes in Inglenook?

The road cycling routes in Inglenook are highly rated by the komoot community, with an average score of 4.0 stars. Cyclists often appreciate the varied terrain, including lake loops and challenging climbs, which provide a diverse and engaging riding experience.

Are there any long-distance road cycling loops around Inglenook?

Yes, there are several long-distance loops. For example, the Squantz Pond – Bulls Bridge loop from New Fairfield is a difficult 54.7-mile route with over 3,300 feet of elevation gain, offering a substantial ride through the region.

What is the best time of year to go road cycling in Inglenook?

Given the region's characteristics of lakes and hilly terrain, spring and fall generally offer the most pleasant conditions for road cycling in Inglenook. Temperatures are milder, and the natural scenery is vibrant, whether with spring blossoms or autumn foliage. Summer can be warm, and winter may bring colder temperatures and potential for icy conditions on some roads.

Are there any routes that combine lake views with significant elevation changes?

Absolutely. Many routes in Inglenook are defined by lake loops and hilly terrain. The Squantz Pond – Squantz Pond loop from Candlewood Mountain is a moderate 35.1-mile path that features significant elevation gain while circling Squantz Pond, offering both scenic views and a good workout.

Where can I find parking for road cycling routes in Inglenook?

While specific parking locations for each route are best checked on individual komoot tour pages, areas near popular attractions like Squantz Pond State Park often provide designated parking facilities suitable for accessing nearby cycling routes.

Can I find cafes or places to stop for refreshments along the road cycling routes?

The region around Inglenook, with its mix of natural areas and local communities, likely offers opportunities for refreshments. For instance, the Fife 'n Drum Restaurant & Inn loop from Sherman suggests that routes may pass through or near towns with amenities like restaurants and inns, where you can find cafes or places to refuel.

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