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Road cycling routes around Brentwood traverse a landscape characterized by agricultural lands, orchards, and rolling hills. The region offers a variety of terrain, from paved paths to routes with notable elevation gains. Cyclists can explore areas featuring farmlands and vineyards, providing a scenic backdrop for rides. The network includes options for various fitness levels, from easy loops to more challenging ascents.
Last updated: July 2, 2026
24
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
18
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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12
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
12
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
14
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Towering 155 feet above the valley, the Double Arch Bridge gives you a commanding view over the surrounding landscape. It was constructed in 1994 and received the Presidential Award for Design Excellence in 1995.
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River Park Trail is a trail that follows the Little Harpeth River, and it is a great multi-use trail for bikers and hikers in the area to enjoy. It can get busy here in the summer, and for good reason, the green area that it passes through is picturesque.
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The Boiling Springs Trail (also referred to as the Ravenwood Trail) is part of the greater Brentwood Parks Trail System. This paved path is popular for cycling, running, and walking and is easy to follow. It connects to a few other trails and parks and is a popular option for those commuting through this part of town.
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Marcella Vivrette Smith Park, formerly Ravenswood Farm and home to the Ravenswood Mansion, opened in 2014. There are over six miles of trails through forests and fields, passing the historic Ravenswood Mansion from 1825. This hilly area is a great spot for a hike. Keep your eyes open here for deer and wild turkeys, which are common. The trails are usually uncrowded, and it's a nice area to get out and grab some solitude.
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Also known as Fewkes Group Archaeological Site, Boiling Springs Mounds is a Native American Archaeological Site. Between 1000-1450, two different pre-American groups used to live in the region, in different periods with different traditions. These mounds in the area were used for burials and others for ceremonies; there are five mounds in total. The site is named in honor of Dr. J. Walter Fewkes, the Chief of the Bureau of American Ethnology, who has studied the site.
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Also known as Fewkes Group Archaeological Site, Boiling Springs Mounds is a Native American Archaeological Site. Between 1000-1450, two different pre-American groups used to live in the region, in different periods with different traditions. These mounds in the area were used for burials and others for ceremonies; there are five mounds in total. The site is named in honor of Dr. J. Walter Fewkes, the Chief of the Bureau of American Ethnology, who has studied the site.
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You have to use your imagination a bit to see it now, but this area was the home a settlement of the Mississippian Culture from roughly 900-1450 AD. The most prominent remains are the two large earthen mounds that once dominated the landscape along the banks of the Harpeth River.
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Old Town is an archaeological site in Williamson County, Tennessee near Franklin. The site includes the remnants of a Native American village and a mound complex of the Mississippian culture and is listed on the National Register of Historic Places (NRHP) as Old Town Archaeological Site
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There are over 20 road cycling routes around Brentwood, offering a diverse range of experiences for cyclists. These routes are highly rated by the komoot community, with an average score of 4.5 stars from over 4 reviews.
Road cycling routes around Brentwood traverse a landscape characterized by agricultural lands, orchards, and rolling hills. You'll find a variety of terrain, from paved paths through scenic farmlands and vineyards to routes with notable elevation gains, particularly in areas like the Clayton Ranch loop mentioned in regional research.
Yes, Brentwood offers road cycling routes for various fitness levels. You can find easy loops, moderate paths, and more challenging ascents. For instance, there are 6 easy routes, 15 moderate routes, and 1 difficult route available, ensuring options for everyone from casual riders to experienced cyclists.
For those seeking a longer and more challenging ride, consider the Old Town archaeological site – Old Town Bridge loop from Brentwood High School. This moderate route spans approximately 38.8 miles (62.4 km) and features over 1750 feet (533 m) of elevation gain, taking around 3 hours and 15 minutes to complete.
Yes, if you're looking for an easier and shorter ride, the Boiling Springs Mounds – Boiling Springs Mounds loop from Ravenwood High School is a good option. This moderate route is about 17.4 miles (28 km) long with around 490 feet (150 m) of elevation gain, typically completed in about 2 hours and 30 minutes.
Many routes pass through Brentwood's rich agricultural lands, featuring expansive farmlands, orchards, and vineyards. You might also encounter regional preserves and parks like Round Valley Regional Preserve or Marsh Creek Regional Trail. Specific highlights include the Old Town archaeological site, which is part of some routes, and the Bridge of the Harpeth River Greenway.
While many road cycling routes are designed for experienced riders, Brentwood's extensive greenway trail system offers multi-use paths that are ideal for families. These paved trails connect various parks and neighborhoods, providing a safer and more scenic environment away from traffic, suitable for all ages.
The region's pleasant climate generally makes road cycling enjoyable for much of the year. Spring and fall offer comfortable temperatures and beautiful scenery, especially when orchards are in bloom or during the harvest season. Summer can be warm, so early morning or late afternoon rides are often preferred.
Yes, many of the road cycling routes around Brentwood are designed as loops, allowing you to start and end at the same point. Examples include the popular Boiling Springs Mounds – Marcella Vivrette Smith Park loop from Owl Creek Park and the Old Town Bridge – Old Town archaeological site loop from Brentwood High School.
Many routes start near public parks or schools, which often provide parking facilities. For example, routes like the Boiling Springs Mounds – Marcella Vivrette Smith Park loop begins from Owl Creek Park, and others from Brentwood High School, where parking may be available. It's advisable to check specific starting points for parking details.
The area is highly rated by the komoot community, with an average score of 4.5 stars. Reviewers often praise the scenic agricultural lands, the variety of terrain from gentle farmlands to rolling hills, and the well-maintained roads that offer a pleasant cycling experience. The diverse route options catering to different skill levels are also frequently highlighted.
While specific café stops are not detailed for every route, Brentwood and its surrounding towns like Oakley and Discovery Bay offer various amenities. Cycling groups in the region often incorporate stops into their rides, and you'll find local cafes, pubs, and farm stands, especially during harvest season, in the towns and villages you pass through.


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