Looking for the best trails around Monticello?

Explore the best rated trails in Monticello, FL. Whether you're looking for an easy walking trail or a bike trail like the Miccosukee Greenway and Goose Pond Trail. With more than 15 trails covering 102 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

Four Freedoms Trail

Trail needs some love

November, 2022 by vc2019

Good route except for .5 mile near traffic. The trail needs to be cleaned off and add warnings about bumpy pavement.

Tallahassee-St. Marks Historic Railroad State Trail

A flat out and back

September, 2022 by robert.richter89

I began my ride at the North Trailhead in Tallahassee and ended almost 16 miles at the southern terminus in St. Marks. It was a very hot Labor Day but the trail is almost entirely shaded which provided relief from the sun. The trail is entirely paved, completely flat and well marked. There a few cracks in places that might give you a shake but won't cause you to pop a tire. There are many very small road crossing but I can count on one hand how many cars I encountered on them. The one or two larger road crossings were also very quiet. There are many shaded benches to rest and there are about three or four bathrooms along the trail but I can't comment on their condition.

My only complaint is the lack of scenery, its mostly flanked by small homes, brush and runs next to a residential street for the majority of the trail. St. Marks is a great little place to get something to eat along the river and enjoy a much deserved rest.

Tom White Linear Park

Good trail from downtown. A number of stops through town. Trail gets rough near the airport, southern end of trail - not good to go fast on road bikes; tree roots lifting the blacktop. Scenic, relaxing ride.

July, 2022 by rlago49

Good trail from downtown. A number of stops through town. Trail gets rough near the airport, southern end of trail - not good to go fast on road bikes; tree roots lifting the blacktop. Scenic, relaxing ride.


Miccosukee Greenway

A Gem!

July, 2022 by doubled3

Two of us rode on July 16th, 2022. This was our 2nd foray but this time we started at the parking lot on Fleischman Road. A wide packed gravel trail that is just hilly enough. There are a few open areas but 90-95 percent of the trail is shaded. We logged 14.8 miles on our out and back ride and did not go on any side trails - yet. Available toilet facilities were clean and in good repair. We look forward to riding here on our next visit. Do not depend on water fountains as anything can happen at any time. Bring plenty of water if it's summer. The temp when we returned to the car was 100 degrees F in the open parking lot. The shade on most of the trail made it comfortable to ride.

Four Freedoms Trail

Good Potential but Poorly Maintained

May, 2022 by bobsteele

Rode in March 2022 and could not enjoy the ride because of all the limbs and twigs on the trail. Many stops to clear the way. Trail has good potential but because of the unknown condition at the time, I would check before using.

Four Freedoms Trail

enjoyable over all.

March, 2022 by cyclingtom2014

Rode 8 miles out from Madison and back. Lots of tree debris and some really bumpy spots. Had to concentrate on riding. We weren’t bothered at all by the road noise and thought the variety of scenery and the elevation changes kept it interesting.

Four Freedoms Trail

recent repairs

February, 2022 by skyesdad

Went for a 16 mile run (8 out and back) from Madison while wife rode bike. The paved path was recently cleared of debris and several bumps from tree roots had been repaired with new asphalt. Not the most exciting of trails but it gets you off of the roads and offers some shade.

Miccosukee Greenway

A Wonderful surprise

February, 2022 by 3iqdwkdqe7

Great fun trail. Short up and downs. Crushed stone surface. The erosion control berms were fun. Had 34 & 38 mm tires. Trail under I-10 is the roughest. Total out & back - 14 miles.

Tom White Linear Park

Nice trail for beginners.

February, 2022 by scox2647

The trail is great and mostly in good shape except for the short stretch by the airport, tree roots are pushing up the pavement. Lots of shade along the way, water fountain and benches. We had a great ride!

Tallahassee-St. Marks Historic Railroad State Trail

Worth a Visit

February, 2022 by acewickwire

Jan 2022: Parked and started from the St. Marks end of trail and rode to Wakulla (crossing highway 267). Nice wide paved path with some cracking in the surface making for some less than smooth travel. Not severe but enough to give a bit of roughness. As with most rail-to-trails, lots of straight and fairly flat travel. Did see a few deer along through the woods, lots of woods to the sides. A few others trail users were out but was an early morning and coolish temps. Did see one informational panel along trailside. Plenty of rest stop places with benches and a couple nice looking restrooms. When a bit warmer day would ride further.

Tallahassee-St. Marks Historic Railroad State Trail

Great Beginner Trails

December, 2021 by iseanachai

It was a nice cool Saturday morning. The trails were in great shape. They wind through tall pines and fields of brush. Very nice trails for beginner mountain biking. I would suggest you bring a map as it is easy to get lost as I did. The trails are well worn but do have some sandy areas. The west connector is red clay and runs faster than the other trails. This connector also has some mild hills. It was my first go on these trails but would highly recommend. I will return with my wife in tow for the next go around. Enjoy

Tallahassee-St. Marks Historic Railroad State Trail

fabulous Fall bike ride

November, 2021 by mem9622

We went to the south end of the trail to start our ride. We parked right across from the trail head on the Saint Marks river There’s a little parking lot there that is free during the day but not at night. There are a couple cute little restaurants in the town with outdoor seating and it’s fun to just ride around and look at the old Florida way of life. There are also several parks with restrooms along the water going north and a mini bike trail. Once you start off on the trail, you can go all the way to Tallahassee or do any portion. The trail is very well kept with very little buckling or tree route intrusions etc. it’s all a very nice asphalt trail surface. Mostly it’s shady with an occasional sun break. Lots of little Florida houses and old boats and trees to enjoy along the route. It’s pretty straight so you can go fast or slow. We went on a Thursday and there was very little traffic. It’s much less traveled than the north end of the trail but the whole trail is really really nice. We’ve done the north and the south end. It’s worse a bike ride it’s worth a car ride from Tallahassee down to this trail head

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