5.0
(1)
49
riders
9
rides
Gravel biking around Underhill Flats offers a diverse landscape for riders. The region features a mix of rural roads, agricultural areas, and forested sections, with routes often traversing past orchards, farms, and local landmarks. While named "Flats," the terrain includes rolling hills and moderate ascents, providing varied challenges for gravel cyclists. The area's network of trails connects different communities and natural features, making it suitable for exploring on a gravel bike.
Last updated: May 29, 2026
5.0
(1)
6
riders
46.8km
02:55
750m
750m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
21.2km
01:25
430m
430m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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4
riders
37.7km
02:16
520m
520m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
39.0km
02:18
400m
400m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
24.3km
01:30
370m
370m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Great way to get up the Notch and avoid most of Route 107
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Beautiful Gorge along the route. As tempting as it may be to go in for a swim, don’t, many people have met their end swimming in this gorge.
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Partially maintained Class IV road, totally rideable! Allows you to connect Osgood Hill Road to Cambridge Road. Ride from Fairfax to Essex on Gravel and avoid route 128
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Great country store just across the Westford Green. Decent sandwiches and cold drinks!
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The Grist Mill Covered Bridge, which is also known as the Scott Covered Bridge, the Bryant Covered Bridge, or the Canyon Covered Bridge, spans the Brewster River near the beautiful Brewster River Gorge and falls. This bridge is one of a small number of surviving Burr arch truss bridges in the state and was built in the 19th century. In 1974 it was listed on the National Register of Historic Places. There is a nice overlook for the Brewster Falls not far from here, down a short trail if you wanted to leave your bikes and go on a short walk.
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The West Farm Trail is located within the Brewster Uplands and loops through the woods northeast of the gorge, past farmlands that are still in use. There are several trails that connect to The Alden Bryan Trail, which parallels the river, and the Brewster Pond Loop, allowing you to lengthen your hike if you choose. Please note that two farms and associated fields on the property are not open to public recreation; they are working farms so please be respectful as you hike around here.
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From the main parking area, you must walk back on the road and through the Grist Mill Covered Bridge. Also known as the Scott Covered Bridge, the Bryant Covered Bridge,or the Canyon Covered Bridge, this bridge is one of a small number of surviving Burr arch truss bridges in the state and was built in the 19th century. In 1974 it was listed on the National Register of Historic Places.
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Historical covered bridge that was built in 1938. Currently, there is a concrete bridge to cross Brown's River, but the covered bridge has been preserved for visitors to see in its original form.
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Underhill Flats offers a varied landscape for gravel biking, characterized by a mix of rural roads, agricultural areas, and forested sections. While the name suggests flat terrain, you'll encounter rolling hills and moderate ascents, providing diverse challenges. Routes often traverse past orchards, farms, and local landmarks, connecting different communities and natural features.
Yes, several routes are suitable for those looking for a more moderate experience. For instance, the Chapin Orchard – Brookside Cemetery loop from Essex is a moderate 19.9-mile trail that explores rural landscapes. Another good option is the West Farm Trail – Grist Mill Bridge loop from Valley Dream Farm, a moderate 15.1-mile trail through agricultural areas.
For experienced gravel bikers seeking a challenge, the Union Bank Cambridge loop from Stevensville is a difficult 29.0-mile path. This longer route features significant elevation gain and traverses varied terrain between communities, offering a more demanding ride.
Yes, many of the gravel bike trails in Underhill Flats are designed as loops, allowing you to start and finish in the same location. Examples include the Chapin Orchard – Brookside Cemetery loop from Essex, the Union Bank Cambridge loop from Stevensville, and the Underhill Pond loop from Underhill.
The routes often pass by local landmarks and natural features. You might encounter orchards, farms, and historic sites like the Grist Mill Bridge on the West Farm Trail loop. The region also features attractions such as Mount Mansfield Summit and the unique rock formation Cantilever Rock, which are accessible nearby.
While specific viewpoints directly on every gravel route aren't detailed, the region is known for scenic vistas. You can find notable viewpoints like Mansfield's Lower Lip in the broader area, offering panoramic views that might be incorporated into or accessed from some of the longer rides.
The best time for gravel biking in Underhill Flats is typically from late spring through early autumn (May to October). During these months, the weather is generally mild, and the trails are less likely to be muddy or covered in snow, providing optimal riding conditions. Always check local weather forecasts before heading out.
The gravel routes in Underhill Flats often connect different communities and traverse agricultural areas. While specific cafes aren't listed for every route, riding through towns like Essex or Cambridge (as featured in the Union Bank Cambridge loop) will likely provide opportunities to find local eateries or stores for refreshments.
The duration varies depending on the route and your pace. Moderate trails like the Chapin Orchard – Brookside Cemetery loop (19.9 miles) can take around 1 hour 47 minutes. Longer, more difficult routes such as the Union Bank Cambridge loop (29.0 miles) might require over 2 hours 50 minutes to complete.
The gravel biking routes in Underhill Flats are highly rated by the komoot community, with an average score of 5.0 stars from 5 reviews. Riders often praise the diverse terrain, the mix of rural roads and forested sections, and the scenic beauty of the agricultural landscapes and local landmarks.
Yes, the West Farm Trail – Grist Mill Bridge loop from Valley Dream Farm is a notable route that leads through agricultural areas and past a historic mill bridge, offering a glimpse into the region's past. Another route, the Church Converted into a Home loop from Large Rock, passes by an interesting repurposed building.


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