Holly Hill Trails and Maps

332 Reviews

Looking for the best trails around Holly Hill?

Find the top rated trails in Holly Hill, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.

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  • Length
Activities
Length
Surfaces
Type
22 Results
Activities
Length
Surfaces
Type

Cady Way Trail

6.5 mi
State: FL
Asphalt

Casselberry Greenway Trail

5 mi
State: FL
Asphalt

Cross Seminole Trail

22.8 mi
State: FL
Asphalt

Cross Volusia Trail

5.3 mi
State: FL
Concrete

East Central Regional Rail Trail

15 mi
State: FL
Asphalt, Concrete

Flagler Trail

14 mi
State: FL
Concrete, Dirt, Grass, Gravel, Sand

Halifax River Trail

5.9 mi
State: FL
Concrete

Kewannee Trail

1.7 mi
State: FL
Asphalt

Lehigh Greenway Rail Trail

6.6 mi
State: FL
Asphalt

Little Econ Greenway

8 mi
State: FL
Asphalt

Orlando Urban Trail

2.6 mi
State: FL
Asphalt, Concrete

Palatka Urban Trail

2 mi
State: FL
Asphalt

Ponce Inlet Trail

3.5 mi
State: FL
Concrete

Sanford Riverwalk

1 mi
State: FL
Asphalt

Seminole Wekiva Trail

14 mi
State: FL
Asphalt

Spring to Spring Trail

17 mi
State: FL
Asphalt

Sweetheart Trail

1.5 mi
State: FL
Concrete

Titusville Multi-Use Trail

1.9 mi
State: FL
Asphalt

Tomoka State Park Trail

2.1 mi
State: FL
Concrete
Accordion

US 92 Trail

2.6 mi
State: FL
Asphalt

West Orange Trail

22 mi
State: FL
Asphalt, Concrete, Dirt, Woodchips
Trail Image Trail Name States Length Surface Rating
The Cady Way Trail runs from the intersection of Aloma Avenue and Howell Branch Road/Hall Road (just east of Goldenrod Park in Goldenrod) west and south to Colonial Town Center (Fashion Square Mall)...
FL 6.5 mi Asphalt
Casselberry Greenway Trail (formerly known as Wirz Trail) is a 5-mile multi-use path zig-zagging through Casselberry, Florida, linking neighborhoods to schools, parks and shopping.  The first segment...
FL 5 mi Asphalt
Stretching from Orlando’s densely populated outskirts to the sleepy bedroom communities of Oviedo, Winter Springs, and Lake Mary, the Cross Seminole Trail provides crucial residential links in this...
FL 22.8 mi Asphalt
The Cross Volusia Trail will one day link the east and west sides of Volusia County, stretching 20 miles from Lake Beresford to the coastal city of New Smyrna Beach. Currently, it runs through the...
FL 5.3 mi Concrete
When complete, the East Central Regional Rail Trail will extend more than 50 miles between DeBary and Edgewater with another segment to Titusville. The trail will connect urban centers with the...
FL 15 mi Asphalt, Concrete
A rail-trail that's a bit wild and off the beaten path, the Flagler Trail runs for around fourteen miles through rural Seminole County, to the northwest of Orlando. Nearly the entirety of the trail is...
FL 14 mi Concrete, Dirt, Grass, Gravel, Sand
The Halifax River Trail (also known as the Halifax River Greenway) will one day stretch 11 miles from Port Orange to Ormond Beach on Florida’s northeast coast. It’s currently open in two segments...
FL 5.9 mi Concrete
Kewannee Trail is a charming, neighborhood trail in Maitland, Florida. More than just a recreation path, the trail is popular as a connective line from the neighborhood to several destinations...
FL 1.7 mi Asphalt
The Lehigh Trail is located in Flagler County on a former railroad corridor comprising 195 acres. The railroad spur once carried cement and other materials to and from the Lehigh Portland Cement Plant...
FL 6.6 mi Asphalt
The Little Econ Greenway trail is just one section of the Orlando area's many fine trails. features riverside recreation, picnicking, wildlife watching, and canoe trails. It also features a canal...
FL 8 mi Asphalt
Orlando Urban Trail offers a pleasant way for pedestrians and bicyclists to reach a number of recreational and cultural attractions in the city's northern neighborhoods. It winds by several lakes,...
FL 2.6 mi Asphalt, Concrete
The Palatka Urban Trail provides a safe bike-ped route over St. John’s River via Memorial Bridge. The trail is a connector between the Lake Butler-Palatka section and the Palatka-St. Augustine Trail....
FL 2 mi Asphalt
The Palatka-to-St. Augustine State Trail currently runs through the communities of Armstrong, Elkton, and Vermont Heights in northeastern Florida. Much of the route follows State Route 207, hence its...
FL 18 mi Asphalt
The Ponce Inlet Trail stretches down Florida's eastern seashore from the southern outskirts of Daytona Beach to the small coastal town of Ponce Inlet. The trail begins at Major Street and follows S....
FL 3.5 mi Concrete
The Sanford Riverwalk Trail follows the shoreline of Lake Monroe in Sanford, FL, north of Orlando. The riverwalk extends from US 17-92 to Mellonville Avenue and is one of the most scenic paved trails...
FL 1 mi Asphalt
Running along the former line of the Orange Belt Railway, the Seminole-Wekiva Trail offers a peaceful alternative to the busy streets of Altamonte Springs. This popular, well-marked, 14-mile route is...
FL 14 mi Asphalt
If you're traveling to central Florida, you won't want to miss the Spring to Spring Trail, which connects a number of small, friendly towns between Orlando and Daytona Beach, as well as many of the...
FL 17 mi Asphalt
The Sweetheart Trail offers a paved route nestled between Beach Street and the Halifax River in Daytona Beach. It's named after a yacht owned by Charles Grover Burgoyne, a successful businessman who...
FL 1.5 mi Concrete
The Titusville Multi-Use Trail, also known as the Wuesthoff Trail, is a short and pleasant paved path located in the southern outskirts of the city of Titusville. The trail runs through Wuesthoff Park...
FL 1.9 mi Asphalt
Tomoka State Park Trail offers a short, paved route through the park in northeastern Florida's Ormond Beach (just north of Daytona Beach). The easy-to-ride trail runs through the woods alongside Beach...
FL 2.1 mi Concrete
Accordion
The US 92 Trail travels across northern DeLand, closely following the north side of the highway known locally as International Speedway Boulevard because it passes the famous racetrack at Daytona...
FL 2.6 mi Asphalt
Connecting small communities and suburban neighborhoods, the 22-mile West Orange Trail is one of Florida's most popular rail-trails, thanks to its reputation and proximity to metro Orlando. Fifteen...
FL 22 mi Asphalt, Concrete, Dirt, Woodchips

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Trails by activity

East Central Regional Rail Trail

FL - 15 miles

When complete, the East Central Regional Rail Trail will extend more than 50 miles between DeBary and Edgewater with another segment to Titusville. The trail will connect urban centers with the...

Ponce Inlet Trail

FL - 3.5 miles

The Ponce Inlet Trail stretches down Florida's eastern seashore from the southern outskirts of Daytona Beach to the small coastal town of Ponce Inlet. The trail begins at Major Street and follows S....

Tomoka State Park Trail

FL - 2.1 miles

Tomoka State Park Trail offers a short, paved route through the park in northeastern Florida's Ormond Beach (just north of Daytona Beach). The easy-to-ride trail runs through the woods alongside Beach...

Titusville Multi-Use Trail

FL - 1.9 miles

The Titusville Multi-Use Trail, also known as the Wuesthoff Trail, is a short and pleasant paved path located in the southern outskirts of the city of Titusville. The trail runs through Wuesthoff Park...

Accordion

Cross Seminole Trail

FL - 22.8 miles

Stretching from Orlando’s densely populated outskirts to the sleepy bedroom communities of Oviedo, Winter Springs, and Lake Mary, the Cross Seminole Trail provides crucial residential links in this...

Orlando Urban Trail

FL - 2.6 miles

Orlando Urban Trail offers a pleasant way for pedestrians and bicyclists to reach a number of recreational and cultural attractions in the city's northern neighborhoods. It winds by several lakes,...

Spring to Spring Trail

FL - 17 miles

If you're traveling to central Florida, you won't want to miss the Spring to Spring Trail, which connects a number of small, friendly towns between Orlando and Daytona Beach, as well as many of the...

West Orange Trail

FL - 22 miles

Connecting small communities and suburban neighborhoods, the 22-mile West Orange Trail is one of Florida's most popular rail-trails, thanks to its reputation and proximity to metro Orlando. Fifteen...

Halifax River Trail

FL - 5.9 miles

The Halifax River Trail (also known as the Halifax River Greenway) will one day stretch 11 miles from Port Orange to Ormond Beach on Florida’s northeast coast. It’s currently open in two segments...

Kewannee Trail

FL - 1.7 miles

Kewannee Trail is a charming, neighborhood trail in Maitland, Florida. More than just a recreation path, the trail is popular as a connective line from the neighborhood to several destinations...

Seminole Wekiva Trail

FL - 14 miles

Running along the former line of the Orange Belt Railway, the Seminole-Wekiva Trail offers a peaceful alternative to the busy streets of Altamonte Springs. This popular, well-marked, 14-mile route is...

Little Econ Greenway

FL - 8 miles

The Little Econ Greenway trail is just one section of the Orlando area's many fine trails. features riverside recreation, picnicking, wildlife watching, and canoe trails. It also features a canal...

Cady Way Trail

FL - 6.5 miles

The Cady Way Trail runs from the intersection of Aloma Avenue and Howell Branch Road/Hall Road (just east of Goldenrod Park in Goldenrod) west and south to Colonial Town Center (Fashion Square Mall)...

Cross Volusia Trail

FL - 5.3 miles

The Cross Volusia Trail will one day link the east and west sides of Volusia County, stretching 20 miles from Lake Beresford to the coastal city of New Smyrna Beach. Currently, it runs through the...

Palatka Urban Trail

FL - 2 miles

The Palatka Urban Trail provides a safe bike-ped route over St. John’s River via Memorial Bridge. The trail is a connector between the Lake Butler-Palatka section and the Palatka-St. Augustine Trail....

Sweetheart Trail

FL - 1.5 miles

The Sweetheart Trail offers a paved route nestled between Beach Street and the Halifax River in Daytona Beach. It's named after a yacht owned by Charles Grover Burgoyne, a successful businessman who...

Casselberry Greenway Trail

FL - 5 miles

Casselberry Greenway Trail (formerly known as Wirz Trail) is a 5-mile multi-use path zig-zagging through Casselberry, Florida, linking neighborhoods to schools, parks and shopping.  The first segment...

Palatka-to-St. Augustine State Trail

FL - 18 miles

The Palatka-to-St. Augustine State Trail currently runs through the communities of Armstrong, Elkton, and Vermont Heights in northeastern Florida. Much of the route follows State Route 207, hence its...

US 92 Trail

FL - 2.6 miles

The US 92 Trail travels across northern DeLand, closely following the north side of the highway known locally as International Speedway Boulevard because it passes the famous racetrack at Daytona...

Lehigh Greenway Rail Trail

FL - 6.6 miles

The Lehigh Trail is located in Flagler County on a former railroad corridor comprising 195 acres. The railroad spur once carried cement and other materials to and from the Lehigh Portland Cement Plant...

Casselberry Greenway Trail

FL - 5 miles

Casselberry Greenway Trail (formerly known as Wirz Trail) is a 5-mile multi-use path zig-zagging through Casselberry, Florida, linking neighborhoods to schools, parks and shopping.  The first segment...

Tomoka State Park Trail

FL - 2.1 miles

Tomoka State Park Trail offers a short, paved route through the park in northeastern Florida's Ormond Beach (just north of Daytona Beach). The easy-to-ride trail runs through the woods alongside Beach...

US 92 Trail

FL - 2.6 miles

The US 92 Trail travels across northern DeLand, closely following the north side of the highway known locally as International Speedway Boulevard because it passes the famous racetrack at Daytona...

Sanford Riverwalk

FL - 1 miles

The Sanford Riverwalk Trail follows the shoreline of Lake Monroe in Sanford, FL, north of Orlando. The riverwalk extends from US 17-92 to Mellonville Avenue and is one of the most scenic paved trails...

Accordion

Palatka-to-St. Augustine State Trail

FL - 18 miles

The Palatka-to-St. Augustine State Trail currently runs through the communities of Armstrong, Elkton, and Vermont Heights in northeastern Florida. Much of the route follows State Route 207, hence its...

Spring to Spring Trail

FL - 17 miles

If you're traveling to central Florida, you won't want to miss the Spring to Spring Trail, which connects a number of small, friendly towns between Orlando and Daytona Beach, as well as many of the...

Seminole Wekiva Trail

FL - 14 miles

Running along the former line of the Orange Belt Railway, the Seminole-Wekiva Trail offers a peaceful alternative to the busy streets of Altamonte Springs. This popular, well-marked, 14-mile route is...

East Central Regional Rail Trail

FL - 15 miles

When complete, the East Central Regional Rail Trail will extend more than 50 miles between DeBary and Edgewater with another segment to Titusville. The trail will connect urban centers with the...

Lehigh Greenway Rail Trail

FL - 6.6 miles

The Lehigh Trail is located in Flagler County on a former railroad corridor comprising 195 acres. The railroad spur once carried cement and other materials to and from the Lehigh Portland Cement Plant...

Cross Seminole Trail

FL - 22.8 miles

Stretching from Orlando’s densely populated outskirts to the sleepy bedroom communities of Oviedo, Winter Springs, and Lake Mary, the Cross Seminole Trail provides crucial residential links in this...

Orlando Urban Trail

FL - 2.6 miles

Orlando Urban Trail offers a pleasant way for pedestrians and bicyclists to reach a number of recreational and cultural attractions in the city's northern neighborhoods. It winds by several lakes,...

West Orange Trail

FL - 22 miles

Connecting small communities and suburban neighborhoods, the 22-mile West Orange Trail is one of Florida's most popular rail-trails, thanks to its reputation and proximity to metro Orlando. Fifteen...

Titusville Multi-Use Trail

FL - 1.9 miles

The Titusville Multi-Use Trail, also known as the Wuesthoff Trail, is a short and pleasant paved path located in the southern outskirts of the city of Titusville. The trail runs through Wuesthoff Park...

Little Econ Greenway

FL - 8 miles

The Little Econ Greenway trail is just one section of the Orlando area's many fine trails. features riverside recreation, picnicking, wildlife watching, and canoe trails. It also features a canal...

Flagler Trail

FL - 14 miles

A rail-trail that's a bit wild and off the beaten path, the Flagler Trail runs for around fourteen miles through rural Seminole County, to the northwest of Orlando. Nearly the entirety of the trail is...

Ponce Inlet Trail

FL - 3.5 miles

The Ponce Inlet Trail stretches down Florida's eastern seashore from the southern outskirts of Daytona Beach to the small coastal town of Ponce Inlet. The trail begins at Major Street and follows S....

Sweetheart Trail

FL - 1.5 miles

The Sweetheart Trail offers a paved route nestled between Beach Street and the Halifax River in Daytona Beach. It's named after a yacht owned by Charles Grover Burgoyne, a successful businessman who...

Cross Volusia Trail

FL - 5.3 miles

The Cross Volusia Trail will one day link the east and west sides of Volusia County, stretching 20 miles from Lake Beresford to the coastal city of New Smyrna Beach. Currently, it runs through the...

Halifax River Trail

FL - 5.9 miles

The Halifax River Trail (also known as the Halifax River Greenway) will one day stretch 11 miles from Port Orange to Ormond Beach on Florida’s northeast coast. It’s currently open in two segments...

Palatka Urban Trail

FL - 2 miles

The Palatka Urban Trail provides a safe bike-ped route over St. John’s River via Memorial Bridge. The trail is a connector between the Lake Butler-Palatka section and the Palatka-St. Augustine Trail....

Cady Way Trail

FL - 6.5 miles

The Cady Way Trail runs from the intersection of Aloma Avenue and Howell Branch Road/Hall Road (just east of Goldenrod Park in Goldenrod) west and south to Colonial Town Center (Fashion Square Mall)...

Seminole Wekiva Trail

FL - 14 miles

Running along the former line of the Orange Belt Railway, the Seminole-Wekiva Trail offers a peaceful alternative to the busy streets of Altamonte Springs. This popular, well-marked, 14-mile route is...

East Central Regional Rail Trail

FL - 15 miles

When complete, the East Central Regional Rail Trail will extend more than 50 miles between DeBary and Edgewater with another segment to Titusville. The trail will connect urban centers with the...

Sweetheart Trail

FL - 1.5 miles

The Sweetheart Trail offers a paved route nestled between Beach Street and the Halifax River in Daytona Beach. It's named after a yacht owned by Charles Grover Burgoyne, a successful businessman who...

Accordion

Tomoka State Park Trail

FL - 2.1 miles

Tomoka State Park Trail offers a short, paved route through the park in northeastern Florida's Ormond Beach (just north of Daytona Beach). The easy-to-ride trail runs through the woods alongside Beach...

Flagler Trail

FL - 14 miles

A rail-trail that's a bit wild and off the beaten path, the Flagler Trail runs for around fourteen miles through rural Seminole County, to the northwest of Orlando. Nearly the entirety of the trail is...

Halifax River Trail

FL - 5.9 miles

The Halifax River Trail (also known as the Halifax River Greenway) will one day stretch 11 miles from Port Orange to Ormond Beach on Florida’s northeast coast. It’s currently open in two segments...

Titusville Multi-Use Trail

FL - 1.9 miles

The Titusville Multi-Use Trail, also known as the Wuesthoff Trail, is a short and pleasant paved path located in the southern outskirts of the city of Titusville. The trail runs through Wuesthoff Park...

Cross Volusia Trail

FL - 5.3 miles

The Cross Volusia Trail will one day link the east and west sides of Volusia County, stretching 20 miles from Lake Beresford to the coastal city of New Smyrna Beach. Currently, it runs through the...

Ponce Inlet Trail

FL - 3.5 miles

The Ponce Inlet Trail stretches down Florida's eastern seashore from the southern outskirts of Daytona Beach to the small coastal town of Ponce Inlet. The trail begins at Major Street and follows S....

Palatka Urban Trail

FL - 2 miles

The Palatka Urban Trail provides a safe bike-ped route over St. John’s River via Memorial Bridge. The trail is a connector between the Lake Butler-Palatka section and the Palatka-St. Augustine Trail....

Kewannee Trail

FL - 1.7 miles

Kewannee Trail is a charming, neighborhood trail in Maitland, Florida. More than just a recreation path, the trail is popular as a connective line from the neighborhood to several destinations...

Spring to Spring Trail

FL - 17 miles

If you're traveling to central Florida, you won't want to miss the Spring to Spring Trail, which connects a number of small, friendly towns between Orlando and Daytona Beach, as well as many of the...

US 92 Trail

FL - 2.6 miles

The US 92 Trail travels across northern DeLand, closely following the north side of the highway known locally as International Speedway Boulevard because it passes the famous racetrack at Daytona...

Casselberry Greenway Trail

FL - 5 miles

Casselberry Greenway Trail (formerly known as Wirz Trail) is a 5-mile multi-use path zig-zagging through Casselberry, Florida, linking neighborhoods to schools, parks and shopping.  The first segment...

Little Econ Greenway

FL - 8 miles

The Little Econ Greenway trail is just one section of the Orlando area's many fine trails. features riverside recreation, picnicking, wildlife watching, and canoe trails. It also features a canal...

Sanford Riverwalk

FL - 1 miles

The Sanford Riverwalk Trail follows the shoreline of Lake Monroe in Sanford, FL, north of Orlando. The riverwalk extends from US 17-92 to Mellonville Avenue and is one of the most scenic paved trails...

West Orange Trail

FL - 22 miles

Connecting small communities and suburban neighborhoods, the 22-mile West Orange Trail is one of Florida's most popular rail-trails, thanks to its reputation and proximity to metro Orlando. Fifteen...

Lehigh Greenway Rail Trail

FL - 6.6 miles

The Lehigh Trail is located in Flagler County on a former railroad corridor comprising 195 acres. The railroad spur once carried cement and other materials to and from the Lehigh Portland Cement Plant...

Cross Seminole Trail

FL - 22.8 miles

Stretching from Orlando’s densely populated outskirts to the sleepy bedroom communities of Oviedo, Winter Springs, and Lake Mary, the Cross Seminole Trail provides crucial residential links in this...

Recent Trail Reviews

Cady Way Trail

Hardly Worth it

January, 2018 by buffettbike

My wife and I rode the trail round trip on January 20, 2018. We started at the fashion Square Mall. Construction (no doubt temporary) has destroyed the trail start and parking lot near the post office. We had to ride around the block and intercept the trail where it intersects Maguire. No big deal, but an annoyance nonetheless. The only worthwhile aspect of the next segment of the trail was the the fact that you could connect to a very nice trail that runs around Lake Baldwin and passes the community's downtown area as you circle the lake. The rest of the trail itself up to the big bridge overpass is quite forgettable. From the big overpass to the end of the trail is not even worth riding. Near the end of the trail there is an overlook at Perch Lake. The overlook was populated with a bunch of seedy looking people, although they seemed not to pay any attention to us on bikes. This trail gets one star for just there actually being a trail there and the other star for the access to the Lake Baldwin trail.

West Orange Trail

Winter Garden Trail Portion

January, 2018 by vidman10

An earlier review suggest that the Winter Garden portion of the trail prevented 5 stars. Sad, as the small town has an excellent historic museum, interesting train museum, excellent and tasty restaurants. Slow down, stop and smell the roses. Biking is not only an adventure, it is meant to be enjoyed as well.

East Central Regional Rail Trail

lots of construction now happening

December, 2017 by mikemonett

Yesterday, December 4th, 2017, I investigated the progress on this extensive forked trail, which may be totally finished as early as next year. East from Enterprise, it now ends at Maytown and Guise Roads east of Osteen. The gap between there and Gobbler's Lodge Road/Maytown Road is funded for construction in 2018. From Gobbler's Lodge east to Lake Harney Road along Maytown, construction is just starting. From Lake Harney Road clear up to the trailhead and parking in Edgewater (near Cow Lick and Route 442), construction is advancing, with many miles already asphalt. The other fork, going southeast into Titusville, I will check on soon.

Accordion

Sweetheart Trail

Short Flat Trail

November, 2017 by ourtrooper

It was nice and clean. Some parts are dog friendly. The board walks are wide and runnable. There were some homeless people camping around the area. But is very flat, so we ran the Hwy 92 Bridge over and back to add a hill.

West Orange Trail

west Orange bike trail

November, 2017 by ittybritty

Wonderful paved trail through neighborhoods, nature, & historic old small towns. Lots to do on trail and offers more than others. Would ride again !

Cross Seminole Trail

Wish it connected to Wekiva Trail @ I-4

November, 2017 by clairemonet2008

There are many busy intersections. It’s not as shady as Wekiva Trail either, so I can’t go as far with my dog.

Little Econ Greenway

Fun dirt/sand trail

October, 2017 by rstotts37

Trail difficulty is intermediate, but if you just want to take it easy, you can stick to the wide service trails. Definitely would recommend as it has great scenery with some wildlife.

Flagler Trail

flooded

October, 2017 by julie.tausch

this trail could've been fun but it was flooded in the section where we tried to enter. Maybe we'll have better luck next time!

West Orange Trail

Trail perfect!

September, 2017 by ken.kentner

The trail is beautiful! Great for all types of riders. Family friendly to serious riders. Short or long rides the trail is the perfect place for exercise. I love the casual rides with my family. Also, love the long rides on my road bike for serious but fun workouts. Beautiful scenery to enjoy all throughout trail. One of the best bike trails in the region.

East Central Regional Rail Trail

Great Ride

June, 2017 by knitwitti

6/24/17-We started the ride in Osteen where parking was ample and bonus-there was a restroom!!! The ride was great, mostly shaded with beautiful trees and great scenery. We rode 12 miles then went to breakfast at the Osteen Diner-a perfect Saturday morning! Highly recommend no matter what level of rider you are.

East Central Regional Rail Trail

The Trail is Longer

May, 2017 by garybear62

This trail does not end at Draa Road in Titusville. If you keep following the path, you'll cross over Garden Street, on an old train bridge (I believe), and ends up at Boggs Gases on Main Street in Old Downtown Titusville. The city has even created huge bike lanes through old town for cyclists. The lanes are as wide as car lanes!

East Central Regional Rail Trail

Hugh Error

April, 2017 by chmielewski2008

The length of the trailer is less than 5 miles not 15. Otherwise it's a beautiful trail the stretch the legs along with the tires on your bike for a brief distance.

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