61
riders
7
rides
Gravel biking around Lakeside Woods offers diverse routes characterized by extensive unpaved segments and significant elevation changes. The region features varied terrain, including forest roads and challenging uphill sections. These routes often provide long distances and a sense of solitude for riders. The landscape is suitable for gravel bikes with appropriate tire setups.
Last updated: July 11, 2026
16
riders
126km
07:36
1,630m
1,630m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
13
riders
98.8km
05:33
1,110m
1,110m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5
riders
63.5km
03:52
820m
820m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
38.6km
02:36
730m
730m
Hard gravel ride. Very good fitness required. You may need to push your bike for some segments of this route.
2
riders
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 part of Upper Grassy Hill Road runs parallel to this small grass airstrip with its old hangar, where you might catch sight of a plane.
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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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There are 6 gravel bike routes documented in this guide for Lakeside Woods. These routes are generally characterized by extensive unpaved segments and significant elevation changes, offering a challenging experience for riders.
Gravel biking in Lakeside Woods features diverse terrain, including long forest roads, challenging uphill sections, and extensive unpaved segments. The region's landscape is well-suited for gravel bikes, often requiring appropriate tire setups for logging roads and varied surfaces.
The gravel bike routes currently featured in Lakeside Woods are primarily classified as difficult, with substantial elevation gain and long distances. There are no easy or moderate routes listed in this guide, making the area more suitable for experienced riders.
For a challenging ride, consider the River Trail – Tracy Road Gravel Route loop from New Milford, which is 78.5 miles long with significant elevation. Another demanding option is the River Trail – Bulls Bridge loop from New Milford, covering 70.1 miles with considerable climbing.
Yes, all the gravel routes in this guide are loop trails. For example, you can explore the Lake Waramaug State Park – River Trail loop from New Milford, a 39.5-mile route through diverse landscapes, or the Lake Waramaug State Park – Steep Rock Tunnel loop from Raven Rock Preserve, which is 34.7 miles long.
While riding, you might encounter scenic areas like Squantz Pond State Park or the tranquil waters of Squantz Pond. The River Trail itself offers picturesque views, and you can also pass through natural areas like Harrybrooke Park.
Given that all routes in this guide are classified as difficult and involve significant distances and elevation, Lakeside Woods may not be ideal for family-friendly gravel biking, especially with younger children or beginners. The trails are more suited for experienced riders seeking a challenging adventure.
General lakeside regions for gravel biking often offer diverse opportunities throughout the year. However, for challenging routes with unpaved segments and forest roads, spring and fall typically provide the most pleasant conditions with cooler temperatures and vibrant scenery. Winter riding might be possible but could involve snow or ice, while summer can be hot.
While all routes offer unique experiences, the Mine Hill Preserve – Natalie White Preserve loop from Reservoir Park could be considered a hidden gem. It's a slightly shorter (21.5 miles) but still difficult route that takes you through varied landscapes, offering a sense of solitude away from more frequented paths.
The guide focuses on the trails themselves, which often traverse long forest roads and unpaved segments, providing a sense of solitude. While specific cafe stops are not highlighted along these routes, larger towns or villages near the starting points, such as New Milford, would likely offer amenities for refreshments before or after your ride.


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