68
riders
11
rides
If you've ever tried to plan gravel biking around Bridgewater, you know how overwhelming the options can be. Sifting through countless trails to find the ones genuinely worth your time and effort can feel like a full-time job. That's where we come in. Our komoot community has ridden, mapped, and reviewed these routes, so we've done the legwork to bring you a curated shortlist of the best gravel bike trails in the area.
Bridgewater's gravel biking scene is defined by…
Last updated: May 31, 2026
5.0
(1)
14
riders
50.8km
03:19
790m
790m
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
The River Trail – Bulls Bridge loop from New Milford offers a diverse and scenic gravel biking experience, weaving through rolling hills, dense woodlands, and picturesque river valleys. You'll navigate…

Sign up for free
5
riders
21.3km
01:20
340m
340m
If you're seeking a gravel biking adventure that combines historical intrigue with a solid workout, the Scenic route - Walker Brook Road – Steep Rock Tunnel loop from Roxbury delivers.…
11
riders
The Scenic route - Walker Brook Road – Steep Rock Tunnel loop from Shepaug Valley School offers a dynamic gravel biking experience through the picturesque Steep Rock Preserve. You'll navigate…
5
riders
63.5km
03:52
820m
820m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
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.
0
0
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.
0
0
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.
0
0
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.
1
0
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.
0
0
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.
0
0
fast moving is possible if you're running out of time ..or daylight. Like I did.
0
0
There are over 10 gravel bike trails around Bridgewater, offering a diverse range of experiences. Most of these routes are considered difficult, with a few moderate options available for those seeking a less strenuous ride.
Gravel bike trails in Bridgewater feature a varied landscape, including rolling hills, river valleys, and wooded sections. You'll encounter a mix of gravel roads, hardpack dirt paths, and quiet paved sections, providing a dynamic riding experience. Some routes, particularly in Bridgewater, Virginia, wind through picturesque farm country alongside the Dry River.
While many routes are challenging, there are options for less experienced riders. For example, the Scenic route - Walker Brook Road – Steep Rock Tunnel loop from Roxbury is a moderate 13.2-mile (21.3 km) trail that leads through wooded areas and past notable natural features, making it a good choice for those looking for a shorter, less demanding ride.
Many routes offer beautiful scenery, often following waterways and winding through natural areas. The Steep Rock Tunnel – Scenic route - Walker Brook Road loop from Roxbury is a popular choice, featuring significant elevation gain through varied and picturesque terrain. In Bridgewater, Virginia, routes often pass through charming farm country.
Yes, several routes pass by interesting points. For instance, the Steep Rock Tunnel – Scenic route - Walker Brook Road loop from Roxbury goes near the Steep Rock Tunnel. Other nearby attractions include Squantz Pond State Park and Harrybrooke Park. In Bridgewater, Virginia, you might even encounter friendly Mennonite cyclists and their horse-drawn buggies, adding a unique cultural element.
One of the longest and most challenging routes is the River Trail – Tracy Road Gravel Route loop from New Milford, which spans 78.5 miles (126.3 km) and features extensive elevation gain through riverine landscapes and diverse surfaces.
Absolutely. Many routes in the region are defined by river trails and follow waterways. The River Trail – Bulls Bridge loop from New Milford is a prime example, offering a challenging ride along riverine paths. In Bridgewater, Virginia, routes often run alongside the Dry River, with opportunities to enjoy the water, including a swimming hole known as 'the Slab'.
The komoot community frequently praises the diverse terrain and scenic beauty of the Bridgewater area. Riders often highlight the mix of state-maintained gravel roads and quiet paved sections, as well as the unique cultural encounters, such as seeing Mennonite families in horse-drawn buggies in the Virginia region.
Yes, many of the gravel biking routes around Bridgewater are designed as loops, allowing you to start and end at the same point. Examples include the Steep Rock Tunnel – Scenic route - Walker Brook Road loop from Roxbury and the River Trail – Tracy Road Gravel Route loop from New Milford.
Yes, the Lake Waramaug State Park – River Trail loop from New Milford is a challenging route that takes you near Lake Waramaug State Park. Additionally, the broader Bridgewater region (especially in New Jersey) offers numerous parks like Duke Island Park and Washington Valley Park, which feature trails suitable for biking.
For more details on the specific 'Bridgewater Gravel Ride' in Virginia, which is known for its picturesque farm country and minimal elevation change, you can visit the Harrisonburg Tourism website: visitharrisonburgva.com.


Browse the best Gravel rides in other regions.