22
riders
4
rides
Gravel biking around Inglenook, Connecticut, offers routes through a landscape characterized by forested state parks, scenic river valleys, and well-maintained dirt roads. The region features the Housatonic River and areas like Squantz Pond State Park, providing varied terrain suitable for gravel cycling. These routes often include views of the river and pass through wooded areas, with some sections on unpaved surfaces. The topography includes rolling hills and some more challenging ascents, typical of the Connecticut countryside.
Last updated: May 15, 2026
13
riders
98.5km
05:31
1,110m
1,110m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
63.5km
03:52
820m
820m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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2
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
43.7km
02:50
790m
790m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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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The Mine Hill Preserve covers 360 acres and include the remnants of a 19th century iron making facility, which is now on the National Register of Historical Places. A series of signs along the paths give you the details of iron making process from mining the ore to processing steel.
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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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The Natalie White Preserve is one of many such preserves overseen by the Roxbury Land Trust. Though small there is a short trail leading to a hilltop that affords nice views of the areas and makes for a good picnic spot.
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With its spring in Massachusetts the Housatonic River flows for 149 miles to southern Connecticut into Long Island Sound. The Appalachian Trail follows the river from the covered wooden Bulls Bridge to Falls Village. The river is also a popular whitewater paddling destination with mostly Class I to Class III rapids.
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Explore the Rock Tunnel, a 235-foot passage from the Shepaug Valley Railroad (1872-1948). It's a blast to go under during your hike, giving you a taste of the area's cool railroad history.
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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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The gravel biking routes around Inglenook are generally categorized as 'difficult' on komoot, featuring significant distances and elevation gains. For instance, the shortest route, Steep Rock Tunnel โ Natalie White Preserve loop from New Milford, is still over 41 km with nearly 700 meters of ascent. While the region offers well-maintained dirt roads, the overall topography includes rolling hills and challenging ascents, making it more suitable for experienced gravel bikers.
The Inglenook region is rich in natural beauty. Many routes offer superb views of the Housatonic River. You can also expect to pass through forested state parkland, such as near Squantz Pond State Park and Squantz Pond itself. The River Trail is particularly noted for its scenic beauty, especially during autumn.
Yes, all the gravel biking routes highlighted in this guide are circular loops, designed to bring you back to your starting point. Examples include the challenging River Trail โ Tracy Road Gravel Route loop from New Milford and the Lake Waramaug State Park โ River Trail loop from New Milford, offering varied distances and terrain.
The Inglenook region is particularly scenic during autumn when the changing leaves enhance the routes, especially along the Housatonic River. While gravel biking is possible for much of the year, spring and fall generally offer the most pleasant temperatures and vibrant landscapes. Summer can be warm, and winter conditions might include snow or ice, making some trails less accessible.
While specific regulations for dogs on all gravel trails can vary, many state parks and public lands in Connecticut generally allow dogs on trails, often requiring them to be on a leash. It's always best to check the specific rules for areas like Squantz Pond State Park or Harrybrooke Park before you go.
Given that all routes in this guide are rated 'difficult' and involve significant distances and elevation, they may not be ideal for young children or families seeking very easy rides. However, sections of well-maintained dirt roads, like parts of the River Trail, might be suitable for older, more experienced children or shorter, adapted outings. For a full family experience, consider shorter, less strenuous sections or local park paths.
Many of the routes start from or pass through areas like New Milford, which typically offers public parking options. For routes that traverse state parks or specific trailheads, designated parking lots are usually available. For example, when exploring routes near Squantz Pond State Park, parking facilities within the park would be the most convenient.
While the main routes like the River Trail โ Bulls Bridge loop from New Milford are popular, the extensive network of dirt roads and trails in the region means you can often find quieter sections. Exploring routes that venture deeper into forested areas or away from major attractions might offer a more secluded experience. The guide features five distinct routes, providing options to spread out.
Komoot users frequently praise the scenic beauty of the Inglenook region, particularly the views along the Housatonic River and the experience of riding through forested state parks. The well-maintained dirt roads are also a highlight, offering a true gravel biking experience. The challenging nature of the routes is appreciated by those looking for a significant workout and adventure.
The routes often start or pass through towns like New Milford, where you can find various amenities including cafes, restaurants, and shops to refuel. While the trails themselves might not have direct stops, planning your ride to include a stop in one of the nearby communities is a common practice for gravel bikers in the region.
Winter in Inglenook can bring cold temperatures, snow, and ice, which can make some gravel trails challenging or impassable. While some dedicated riders might venture out, it's important to be prepared for adverse conditions, including potential closures or slippery surfaces. Always check local weather forecasts and trail conditions before planning a winter ride.
Public transport options directly to the trailheads in the more rural parts of Inglenook are limited. Most gravel bikers typically access these routes by car, often starting from towns like New Milford where parking is available. It's advisable to plan for personal transportation to reach the starting points of these trails.


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