Holliston Horseback Riding Trails and Maps

966 Reviews

Looking for the best Horseback Riding trails around Holliston?

Find the top rated horseback riding trails in Holliston, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
24 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

54.6 mi
State: CT
Ballast, Dirt, Gravel

Arkwright Riverwalk

0.8 mi
State: RI
Dirt, Woodchips

Barker Road Trail

0.9 mi
State: MA
Dirt, Grass

Bridle Trail

3 mi
State: MA
Dirt, Sand

Cheshire Rail Trail (Cheshire Branch Rail Trail)

32.9 mi
State: NH
Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Derry Rail Trail

3.6 mi
State: NH
Asphalt

Grand Trunk Trail

6.2 mi
State: MA
Crushed Stone, Dirt, Gravel

Granite Town Rail-Trail

3 mi
State: NH
Ballast, Cinder, Dirt, Grass, Gravel, Sand

Haggetts Rail Trail

2 mi
State: MA
Crushed Stone

Jay McLaren Memorial Trail

2 mi
State: MA
Dirt, Grass, Gravel

Marblehead Rail-Trail

4 mi
State: MA
Asphalt, Dirt, Gravel, Sand

Martin H. Burns Wildlife Management Area Trail

3.4 mi
State: MA
Dirt, Gravel, Sand

Mason Railroad Trail

6.7 mi
State: NH
Ballast, Gravel, Sand

Mass Central Rail Trail

38 mi
State: MA
Crushed Stone, Dirt, Grass

Monadnock Recreational Rail Trail

7.5 mi
State: NH
Asphalt, Gravel

Moosup Valley State Park Trail

5.8 mi
State: CT
Ballast, Crushed Stone, Dirt, Grass, Gravel, Sand

Nashua River Rail Trail

12.3 mi
State: MA, NH
Asphalt

Phoenix Bike Trail

4 mi
State: MA
Asphalt
Accordion

Southern New England Trunkline Trail

21 mi
State: MA
Asphalt, Ballast, Crushed Stone

Topsfield Linear Common and Wenham Rail-Trail

4.9 mi
State: MA
Crushed Stone, Dirt

Washington Secondary Bike Path

19.2 mi
State: RI
Asphalt

Windham Rail Trail

4.3 mi
State: NH
Asphalt
Trail Image Trail Name States Length Surface Rating
The Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...
CT 54.6 mi Ballast, Dirt, Gravel
The Arkwright Riverwalk, founded on a former rail bed purchased from Penn Central Railroad, is located in Coventry, a rural central Rhode Island town that was built around textile mills. The one-mile...
RI 0.8 mi Dirt, Woodchips
Barker Road Trail begins on the town line between North Andover and Boxford in northern Massachusetts, not far from the New Hampshire border. From there, the pathway continues through dense woodlands...
MA 0.9 mi Dirt, Grass
The Blackstone River and Canal Heritage State Park recalls the role of canals in transporting raw materials and manufactured goods between emerging industrial centers. Walk along restored sections of...
MA 3.5 mi Dirt
The abandoned rail bed is predominantly owned by the Town of Marshfield. Sections of the abandoned rail bed are open to the public and actively used for recreational uses such as walking, running,...
MA 3 mi Dirt, Sand
Formerly comprising two separate segments—one running northward from Keene to Walpole, and the other running southward from Keene to Fitzwilliam—the Cheshire Rail Trail now runs a continuous 32.9...
NH 32.9 mi Asphalt, Ballast, Cinder, Dirt, Gravel, Sand
This exquisitely maintained trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. The trail will eventually be part of the Granite State Rail Trail,...
NH 3.6 mi Asphalt
Grand Trunk Trail is part of a larger trail network, the Titanic Rail Trail, which will stretch more than 60 miles through south-central Massachusetts and the northeastern corner of Connecticut along...
MA 6.2 mi Crushed Stone, Dirt, Gravel
Mile 0.0 - DPW Garage  Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...
NH 3 mi Ballast, Cinder, Dirt, Grass, Gravel, Sand
The Haggetts Rail Trail is a short, but sweet unpaved trail located on the periphery of Haggetts Pond, the local reservoir for the nearby town of Andover. Built on part of the former line of the...
MA 2 mi Crushed Stone
Nestled in the woodlands on the northern end of Merrimac in the far northeastern corner of Massachusetts, lies the beautiful Jay McLaren Memorial Trail. The town, once known as West Amesbury, had a...
MA 2 mi Dirt, Grass, Gravel
Shaped like a Y, this 4.1-mile rail-trail connects Marblehead, Salem and Swampscott. From the trail junction in quaint Marblehead, one branch meanders through conservation areas and past harbor...
MA 4 mi Asphalt, Dirt, Gravel, Sand
The rail-trail through the Martin H. Burns Wildlife Management Area begins at the Massachusetts Bay Transportation Authority (MBTA) commuter rail station near downtown Newburyport, a coastal...
MA 3.4 mi Dirt, Gravel, Sand
The Mason Railroad Trail runs for nearly 7 miles from near the New Hampshire–Massachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...
NH 6.7 mi Ballast, Gravel, Sand
A 104-mile rail line was shattered by hurricane in 1938. Today, the corridor is being developed as the Mass Central Rail Trail to be enjoyed by bicyclists, walkers, joggers, and cross-country skiers....
MA 38 mi Crushed Stone, Dirt, Grass
The Monadnock Recreational Rail Trail is a great example of a repurposed rail route that provides safe commuting opportunities while also allowing trail users to escape into forest environments for...
NH 7.5 mi Asphalt, Gravel
This 5.8-mile trail is part of the planned East Coast Greenway, an off-road path that will eventually run from Calais, Maine, to Key West, Florida. The Moosup Valley State Park Trail will connect with...
CT 5.8 mi Ballast, Crushed Stone, Dirt, Grass, Gravel, Sand
The Nashua River Rail Trail is a beautiful and peaceful rural trail extending through the Massachusetts communities of Ayer, Groton, Pepperell and Dunstable. The trail continues into New Hampshire...
MA, NH 12.3 mi Asphalt
Opened in 1999, the Phoenix Bike Trail packs a surprising diversity in its 3.5 miles, passing through woodlands, salt marshes, farms and commercial and residential areas. Tree-lined for much of its...
MA 4 mi Asphalt
Crossing through wooded areas and featuring magnificent wetland vistas, the Rockingham Recreational Rail Trail (Fremont Branch) offers an 18.3-mile trail adventure from Epping to Windham. The northern...
NH 18.3 mi Dirt, Sand
Accordion
The Southern New England Trunk Line Trail (aka the "SNETT") was designated as a National Recreation Trail in 1994. It is built upon a segment of the former right-of-way of the New Haven Railroad's...
MA 21 mi Asphalt, Ballast, Crushed Stone
The trail begins in the small town of Boxford, about 25 miles north of Boston. For just shy of 5 miles, the hard-packed stone-dust pathway follows a former rail bed through Topsfield, meandering...
MA 4.9 mi Crushed Stone, Dirt
The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...
RI 19.2 mi Asphalt
The Windham Rail Trail passes through the woodsy periphery of Windham in southern New Hampshire, but it sits in the heart of the future cross-state Granite State Rail Trail. Its connections to the...
NH 4.3 mi Asphalt

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Trails by activity

Marblehead Rail-Trail

MA - 4 miles

Shaped like a Y, this 4.1-mile rail-trail connects Marblehead, Salem and Swampscott. From the trail junction in quaint Marblehead, one branch meanders through conservation areas and past harbor...

Derry Rail Trail

NH - 3.6 miles

This exquisitely maintained trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. The trail will eventually be part of the Granite State Rail Trail,...

Topsfield Linear Common and Wenham Rail-Trail

MA - 4.9 miles

The trail begins in the small town of Boxford, about 25 miles north of Boston. For just shy of 5 miles, the hard-packed stone-dust pathway follows a former rail bed through Topsfield, meandering...

Granite Town Rail-Trail

NH - 3 miles

Mile 0.0 - DPW Garage  Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...

Accordion

Washington Secondary Bike Path

RI - 19.2 miles

The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...

Nashua River Rail Trail

MA,NH - 12.3 miles

The Nashua River Rail Trail is a beautiful and peaceful rural trail extending through the Massachusetts communities of Ayer, Groton, Pepperell and Dunstable. The trail continues into New Hampshire...

Phoenix Bike Trail

MA - 4 miles

Opened in 1999, the Phoenix Bike Trail packs a surprising diversity in its 3.5 miles, passing through woodlands, salt marshes, farms and commercial and residential areas. Tree-lined for much of its...

Windham Rail Trail

NH - 4.3 miles

The Windham Rail Trail passes through the woodsy periphery of Windham in southern New Hampshire, but it sits in the heart of the future cross-state Granite State Rail Trail. Its connections to the...

Haggetts Rail Trail

MA - 2 miles

The Haggetts Rail Trail is a short, but sweet unpaved trail located on the periphery of Haggetts Pond, the local reservoir for the nearby town of Andover. Built on part of the former line of the...

Blackstone River and Canal Heritage State Park Trail

MA - 3.5 miles

The Blackstone River and Canal Heritage State Park recalls the role of canals in transporting raw materials and manufactured goods between emerging industrial centers. Walk along restored sections of...

Barker Road Trail

MA - 0.9 miles

Barker Road Trail begins on the town line between North Andover and Boxford in northern Massachusetts, not far from the New Hampshire border. From there, the pathway continues through dense woodlands...

Bridle Trail

MA - 3 miles

The abandoned rail bed is predominantly owned by the Town of Marshfield. Sections of the abandoned rail bed are open to the public and actively used for recreational uses such as walking, running,...

Rockingham Recreational Rail Trail (Fremont Branch)

NH - 18.3 miles

Crossing through wooded areas and featuring magnificent wetland vistas, the Rockingham Recreational Rail Trail (Fremont Branch) offers an 18.3-mile trail adventure from Epping to Windham. The northern...

Accordion

Windham Rail Trail

NH - 4.3 miles

The Windham Rail Trail passes through the woodsy periphery of Windham in southern New Hampshire, but it sits in the heart of the future cross-state Granite State Rail Trail. Its connections to the...

Marblehead Rail-Trail

MA - 4 miles

Shaped like a Y, this 4.1-mile rail-trail connects Marblehead, Salem and Swampscott. From the trail junction in quaint Marblehead, one branch meanders through conservation areas and past harbor...

Air Line State Park Trail

CT - 54.6 miles

The Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...

Cheshire Rail Trail (Cheshire Branch Rail Trail)

NH - 32.9 miles

Formerly comprising two separate segments—one running northward from Keene to Walpole, and the other running southward from Keene to Fitzwilliam—the Cheshire Rail Trail now runs a continuous 32.9...

Washington Secondary Bike Path

RI - 19.2 miles

The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...

Jay McLaren Memorial Trail

MA - 2 miles

Nestled in the woodlands on the northern end of Merrimac in the far northeastern corner of Massachusetts, lies the beautiful Jay McLaren Memorial Trail. The town, once known as West Amesbury, had a...

Grand Trunk Trail

MA - 6.2 miles

Grand Trunk Trail is part of a larger trail network, the Titanic Rail Trail, which will stretch more than 60 miles through south-central Massachusetts and the northeastern corner of Connecticut along...

Derry Rail Trail

NH - 3.6 miles

This exquisitely maintained trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. The trail will eventually be part of the Granite State Rail Trail,...

Arkwright Riverwalk

RI - 0.8 miles

The Arkwright Riverwalk, founded on a former rail bed purchased from Penn Central Railroad, is located in Coventry, a rural central Rhode Island town that was built around textile mills. The one-mile...

Mason Railroad Trail

NH - 6.7 miles

The Mason Railroad Trail runs for nearly 7 miles from near the New Hampshire–Massachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...

Nashua River Rail Trail

MA,NH - 12.3 miles

The Nashua River Rail Trail is a beautiful and peaceful rural trail extending through the Massachusetts communities of Ayer, Groton, Pepperell and Dunstable. The trail continues into New Hampshire...

Granite Town Rail-Trail

NH - 3 miles

Mile 0.0 - DPW Garage  Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...

Southern New England Trunkline Trail

MA - 21 miles

The Southern New England Trunk Line Trail (aka the "SNETT") was designated as a National Recreation Trail in 1994. It is built upon a segment of the former right-of-way of the New Haven Railroad's...

Topsfield Linear Common and Wenham Rail-Trail

MA - 4.9 miles

The trail begins in the small town of Boxford, about 25 miles north of Boston. For just shy of 5 miles, the hard-packed stone-dust pathway follows a former rail bed through Topsfield, meandering...

Phoenix Bike Trail

MA - 4 miles

Opened in 1999, the Phoenix Bike Trail packs a surprising diversity in its 3.5 miles, passing through woodlands, salt marshes, farms and commercial and residential areas. Tree-lined for much of its...

Mass Central Rail Trail

MA - 38 miles

A 104-mile rail line was shattered by hurricane in 1938. Today, the corridor is being developed as the Mass Central Rail Trail to be enjoyed by bicyclists, walkers, joggers, and cross-country skiers....

Nashua River Rail Trail

MA,NH - 12.3 miles

The Nashua River Rail Trail is a beautiful and peaceful rural trail extending through the Massachusetts communities of Ayer, Groton, Pepperell and Dunstable. The trail continues into New Hampshire...

Grand Trunk Trail

MA - 6.2 miles

Grand Trunk Trail is part of a larger trail network, the Titanic Rail Trail, which will stretch more than 60 miles through south-central Massachusetts and the northeastern corner of Connecticut along...

Haggetts Rail Trail

MA - 2 miles

The Haggetts Rail Trail is a short, but sweet unpaved trail located on the periphery of Haggetts Pond, the local reservoir for the nearby town of Andover. Built on part of the former line of the...

Derry Rail Trail

NH - 3.6 miles

This exquisitely maintained trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. The trail will eventually be part of the Granite State Rail Trail,...

Accordion

Rockingham Recreational Rail Trail (Fremont Branch)

NH - 18.3 miles

Crossing through wooded areas and featuring magnificent wetland vistas, the Rockingham Recreational Rail Trail (Fremont Branch) offers an 18.3-mile trail adventure from Epping to Windham. The northern...

Moosup Valley State Park Trail

CT - 5.8 miles

This 5.8-mile trail is part of the planned East Coast Greenway, an off-road path that will eventually run from Calais, Maine, to Key West, Florida. The Moosup Valley State Park Trail will connect with...

Bridle Trail

MA - 3 miles

The abandoned rail bed is predominantly owned by the Town of Marshfield. Sections of the abandoned rail bed are open to the public and actively used for recreational uses such as walking, running,...

Granite Town Rail-Trail

NH - 3 miles

Mile 0.0 - DPW Garage  Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...

Monadnock Recreational Rail Trail

NH - 7.5 miles

The Monadnock Recreational Rail Trail is a great example of a repurposed rail route that provides safe commuting opportunities while also allowing trail users to escape into forest environments for...

Mason Railroad Trail

NH - 6.7 miles

The Mason Railroad Trail runs for nearly 7 miles from near the New Hampshire–Massachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...

Martin H. Burns Wildlife Management Area Trail

MA - 3.4 miles

The rail-trail through the Martin H. Burns Wildlife Management Area begins at the Massachusetts Bay Transportation Authority (MBTA) commuter rail station near downtown Newburyport, a coastal...

Air Line State Park Trail

CT - 54.6 miles

The Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...

Jay McLaren Memorial Trail

MA - 2 miles

Nestled in the woodlands on the northern end of Merrimac in the far northeastern corner of Massachusetts, lies the beautiful Jay McLaren Memorial Trail. The town, once known as West Amesbury, had a...

Blackstone River and Canal Heritage State Park Trail

MA - 3.5 miles

The Blackstone River and Canal Heritage State Park recalls the role of canals in transporting raw materials and manufactured goods between emerging industrial centers. Walk along restored sections of...

Washington Secondary Bike Path

RI - 19.2 miles

The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...

Arkwright Riverwalk

RI - 0.8 miles

The Arkwright Riverwalk, founded on a former rail bed purchased from Penn Central Railroad, is located in Coventry, a rural central Rhode Island town that was built around textile mills. The one-mile...

Marblehead Rail-Trail

MA - 4 miles

Shaped like a Y, this 4.1-mile rail-trail connects Marblehead, Salem and Swampscott. From the trail junction in quaint Marblehead, one branch meanders through conservation areas and past harbor...

Cheshire Rail Trail (Cheshire Branch Rail Trail)

NH - 32.9 miles

Formerly comprising two separate segments—one running northward from Keene to Walpole, and the other running southward from Keene to Fitzwilliam—the Cheshire Rail Trail now runs a continuous 32.9...

Barker Road Trail

MA - 0.9 miles

Barker Road Trail begins on the town line between North Andover and Boxford in northern Massachusetts, not far from the New Hampshire border. From there, the pathway continues through dense woodlands...

Topsfield Linear Common and Wenham Rail-Trail

MA - 4.9 miles

The trail begins in the small town of Boxford, about 25 miles north of Boston. For just shy of 5 miles, the hard-packed stone-dust pathway follows a former rail bed through Topsfield, meandering...

Recent Trail Reviews

Burrillville Bike Path

Peaceful, relaxing!

May, 2018 by jimalix54

Yes, the trail is short, but it's very near my home and so great for daily exercise. I'm just beginning to ride my recumbent trike in a serious way, and so I do 3-4 laps every day. It's quiet, peaceful, and very well-maintained.

Upper Charles Trail

Great walking trail

May, 2018 by vito709

Today was the fourth time I walked this trail from holliston walked 2.5 miles and back.

Very easy walking the packed stone and dust pavement. I walk the Henry Hudson trail in NJ nearly every day 5 miles and both these trails provide some of the most interesting sites.

When visiting my family here this provides me a great walk. Wonderful

Cheshire Rail Trail (Cheshire Branch Rail Trail)

North End - Walpole trail head

May, 2018 by ryoung_tl

Clear sunny day in May. Excellent conditions with sunshine and a gentle breeze to keep away the bugs. No ticks encountered. Walked 3.5 miles from the Blackjack Crossing trailhead.

Trail is in great shape although the first .25 mile (going north to the very end from the parking area at the end of Blackjack Crossing) is overgrown and a bit muddy. The first .25 mile stretch going south is the same, but then the surface is very good with crushed rock. There are muddy spots as you pass through the deep cut areas, but other wise, excellent. We walked but mountain bikes would fare very well. Road bikes NOT recommended.

Accordion

Upper Charles Trail

A great long trail in very good condition

May, 2018 by davidbornstein302

Rode the trail this morning (a Wednesday). Very light and friendly walkers with few bikers. Trail is in very good condition -- both the gravel portion in Holliston and the paved portion in Milford. Plenty of benches to pull over and rest if you want...but the trail is about as flat as you get so the riding is easy. Will return many times.

Blackstone River Greenway (MA)

Trash

May, 2018 by jruggieri6568

I’ve been walking the millbury Worcester trail since it opened. It’s so sad what’s become of it. Loaded with trash and broken glass. The trail is now under construction to include a center and lengthening the trail! Why bother if it’s not going to be maintained.

Air Line State Park Trail

Flooded trail

April, 2018 by blueskye

After heavy rain on April 16th, the trail along the Willimantic River is temporarily flooded and impassable,

Washington Secondary Bike Path

hard to find

April, 2018 by fourperch

Hard to find and not well maintained

Fred Lippitt Woonasquatucket River Greenway

The western half of the trail is an easy ride, suitable for kids.

April, 2018 by laurastark

We started our ride in Riverside Park, which has a parking lot, a great playground, and river overlooks. Heading west from there, it's a pleasant trail experience, mostly lined with trees and wildflowers.

Putnam River Trail

Great trail for many purposes

April, 2018 by fencinggirl93

I have used this trail for many purposes. First off, I love finding dog parks and having one right on this trail is a great asset. While it is not my favorite, and dogs being there is rather hit or miss most days, it is still functional for what it is and my dog enjoys going there before or after our walks. There are also a few places where the dogs can access the water if they are into swimming.

Second, it is a pleasant walking trail that is both scenic and urban. It leads from the dog park, follows the river, and into downtown Putnam where lots of shops, restaurants, and more await. As a dog trainer, I highly recommend the trail because you get all kinds of training done in one location (dog on dog greeting, urban walking, trail walking, and socialization with all kinds of people and places).

Also, I recently took up Inline Skating, and this trail is perfect for it! It is smooth all the way, and while there are a couple hills, they aren't very hard to go up or down. I couldn't be happier with my skating experience here.

Lastly there is always a lot of available parking at various points along the trail: at the dog park, near two river access points, near picnic areas, near a band stand, and of course in downtown Putnam itself. It is so convenient! I love this trail and visit it often.

Quinebaug River Trail

Quinebaug River Trail behind Delta Rubber Segment

March, 2018 by mbenitez_tl

It's a fantastic trail. I went after a snowstorm a few days after and to my surprise the trail itself was nice and clean, snow cleared! It runs along the Quinebaug River and it is a very peaceful place for a walk. I have not completed this trail seeing how we just started walking but will look forwarded to completing this trail. Great place for a bike ride, Walk, Run, skate, strollers. All paved once you get to the trail.

Neponset River Greenway

really hope for some expasion

January, 2018 by graftderf

as i live in this area and bike often as possible to reduce my carbon footprint, i like the newponset riverway but i feel its lacking one trail that could be very beneficial, its an unofficial hidden trail running parallel to President golf course that connects Harriet street to Granite street, currently its very rocky and borderline dangerous but im sure its public access road?..? anyway just my 2cents

i had a vision of a foot/bike bridge over to the Newponset river greenway from that unofficial trail would really sweeten the biking commute from east milton to greenway...oh the possibilities

Bay Colony Rail Trail

Map error

December, 2017 by 23rock

This is a delightful section of trail. But, the map does not match the description. The map only shows a piece between Fisher St. and Charles River St. in Needham. But, the trail (as per the description) extends from the Needham / Dover town line at the Charles River, west of Fisher Road, to just west of High Rock St. I particularly like the railroad cross bucks at the street crossings, which have been changed to read "rail trail crossing" and the crosswalk painting which has the cross bars longer to look line cross ties.

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