Westchester Trails and Maps

300 Reviews

Looking for the best trails around Westchester?

Explore the best rated trails in Westchester, FL, whether you're looking for an easy walking trail or a bike trail like the Underline and Limestone Trail . With more than 40 trails covering 325 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Old Cutler Trail

Great for Long Runs

November, 2023 by mvxgn69w9j

If you are training for a marathon, this is one of the best long run trails. It’s clearly split so there isn’t ever really any traffic, it’s shaded about 80-90% of the time, and the views are lovely. People actually say “hello” versus on the beach where I usually run, people look at you like you’re nuts. Parking at the north entrance is easy, 2 hours free from 8am to 10am. Downsides: There weren’t any restrooms or water fountains anywhere. If you are running anything over 6 miles, bring a hydration vest and make sure that you don’t have to use the bathroom

Kitty Roedel Bicycle Path

best trail near me. no cars

November, 2023 by cubavera02

Great trail. No cars. Lots of nature

Turnpike Trail

easy to ride trail

September, 2023 by eremkinv

It goes straight, along side canal. Can’t say it’s picturesque, but for an easy ride works great.


Biscayne-Everglades Greenway

Quiet, nice trail

July, 2023 by alvarado_clara

Nice straight trail by a canal . You can see ducks , birds and fish. It cross some roads but it cars respect the bike cross . Only 2 not great things :1- no close by parking ,2- No shade so come prepared

Florida Keys Overseas Heritage Trail

Bucket list challenge ride for serious, experienced riders.

June, 2023 by dingels75

Heading south from the cold a buddy and I did the 105 miles from Key Largo to Key West in February 2021 splitting the distance at a hotel on Marathon. As mentioned by others, portions had a lot of sidewalks, driveways and store commercial entrances so we had to ride very alert and defensive at all times. There were some long portions on paths and on less-travelled parallel roads where we could relax. Some bridges had dedicated bike lanes but most bridges had a fairly wide shoulder. We used very high lumen, effective white strobes front and rear to give us the best chance of drivers spotting us from a distance. My opinion is that an effective white strobe on the front is mandatory with all of the road crossings. Seven-mile bridge has a 8-10' shoulder so personally it really didn't feel that unsafe but that's a personal decision. We had a blast and hauled you-know-what, it's not for the inexperienced, unprepared or faint of heart. There is plenty of debris to avoid on the shoulder and between the two of us we had 3 flats over two days. We expected that so I suggest carrying two tubes per person and have the ability to change your own flats. We had two non-riding buddies driving our support vehicle and scoping out Tiki Bars for the evening. Due to traffic there is some level of danger involved so take every possible precaution and ride as defensive and safe as possible. We both have Varia radar taillights so we know when vehicles are approaching from behind, they're worth their weight in gold.
We view our Florida Keys ride as an epic experience and one more thing checked off our bucket list.

Florida Keys Overseas Heritage Trail

Some Sections are Good Short Rides

May, 2023 by jallen1804

We rode some sections but avoided the parts of the trail that did not seem safe. Parts of the trail are littered. The trail surface in some parts is in bad shape. But... riding over the water was pretty awesome.

Shark Valley Tram Road

Nature ride

May, 2023 by eguydjr

Arrow straight for 7 miles along a canal, watch for the wild life. Route back has curves but nothing crazy. Great ride, but bring water, No shade .

Florida Keys Overseas Heritage Trail

Enjoyable ride in parts but not for the faint of heart

April, 2023 by kmprechtel

We are in our early 60's and have biked several trails in recent years. We chose the Heritage Trail (Key Largo to Key West) to bike with another couple of who had never biked long distance and point to point with gear. We thought this would be a good trail since it was relatively short in distance and flat. As has been stated in other reviews, parts of the trail were well-maintained, the scenery was beautiful and we had some of the best meals/drinks ever on vacation. HOWEVER, if Florida wants this to be a tourist attraction, much trail work needs to be done. Some sections were littered with trash and road gravel and several pedestrian/cyclist bridges were closed, necessitating crossing to the next key alongside cars and trucks. This trail gave new meaning to "switchbacks" and crossing US1 was often challenging--a few designated crosswalks/caution lights would have been nice (take notes from Sanibel). The most harrowing was south of Cudjoe Key where we shared the road for about 4 miles. There was very little signage in spots and the trail would just end. Our friends opted to take a shuttle across 7 mile bridge due to safety concerns which were valid. We observed speeders who "passed" other cars and came dangerously close to us. Generally most drivers were respectful of cyclists; there was just a lot of traffic. While parts of the trail were great, overall we would not recommend to a novice rider or a low risk taker. Riding sections that are cyclist friendly are recommended until Florida Parks can make significant improvements for a safe and enjoyable thru ride.

Ludlam Drive Trail


April, 2023 by graviator

This is a peaceful trail in the middle of busy surrounding, much like Virginia Gardens itself. It’s lit at night. Surrounded by nice neighborhoods.

Central Trail (FL)

Better walking trail

March, 2023 by downeydc

Narrow asphalt path with lots of walkers. Not sure where 2.2 miles came from. Even up and back was only 1.4. I did notice a patch south of the dog park as I was leaving.

Rickenbacker Trail

Great ride!

February, 2023 by walker923

This is a great ride! Maybe not for everyone— you have a wide, smooth, bright green lane to yourself, but it is adjacent to a busy roadway. That’s plenty good for me. The state park at the end of the trail is very nice, and no traffic there.

Robbins Vista View Trail

better if better described

February, 2023 by vbergerg_tl

This is not a trail, it is a route around some nice parks connected by sidewalks along local roads, some quieter than others. TrailLink map is not especially helpful, it doesn’t even mention that the section along Orange Road and that canal actually starts and ends much further than mapped for the Robbin’s Vista View Trail and is nicer than many of the other street/sidewalk loops shown. A turn by turn with street names is badly needed. I’m

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