Trail Overview

This 6.4-mile point-to-point dirt road connects Clermont and Winter Garden, winding through rolling hills, agricultural farms, and open fields. The well-graded dirt route features minimal elevation changes and sharp 90-degree turns as it circumvents local properties. The trail is highly manageable for high-clearance vehicles, crossover SUVs, and light trucks. Heavy rain can turn the dry, dusty surface into slick mud, causing deep ruts and washboarding. Optional dirt spurs connect to Lake Needham for additional scenic views.

Photos of 5 Mile Road Winter Garden - Clermont

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Difficulty

This is a very easy dirt road that can be handled by most vehicles. It becomes muddy when wet, and not suitable for low clearance sedans.

Technical Rating

keiffer schoeppler

Sep 17, 2026

2026 Jeep Wrangler Rubicon X

Obstructed

Its basically a co struction site now. The 1st part off 27 is sand and some puddles but it quickly runs out onto a new street which if you follow the path runs you into wellness way. I would t bother with this.

David Ives

Apr 10, 2026

Temporarily Closed

Closed GatePosted Sign

John M

Dec 07, 2025

2024 Nissan Titan

Open

Muddy/WetWashboard

Was washboarded for about 60% of trial. Had a small mud hole my daughter loved. Road was a clay like and a little slippery in areas. Second half now has a subdivision to the west going in and round that section there is some trash and a few burn piles of pallets. Towards 27 someone decided todo doughnuts and rutted it pretty good.

Nathan Mitchell

Oct 14, 2025

Open

jose chacon

Sep 21, 2025

Open

Normal

Good day weather, excellent view. Easy terrain or rout.

Dan Van

Aug 23, 2025

Open

NormalMuddy/Wet

Fun trail with a good amount of 2 foot mud holes and a couple of 90° turns. Unfortunately, housing developments are now starting to dot most of the landscape, and they come up right to the road. You can almost smell the countdown to when this will become a paved intersection. Do it now or forever hold your peace. Pro tip.: come around sunset or sunrise.

Dominic James

Aug 19, 2025

2018 Toyota 4Runner

Open

NormalMuddy/Wet

Francisco Medina

Aug 12, 2025

2021 Toyota 4Runner

Open

Normal

Nice easy ride with a few spots of standing water and mud.

Angel Vega

Aug 02, 2025

Open

DustyMuddy/Wet

Jacob Santiago

Jul 13, 2025

Open

NormalDusty

David Speller

Jul 08, 2025

2025 Jeep Wrangler

Open

Normal

Easy ride

Christopher consentino

Jun 09, 2025

2015 RAM 1500

Open

Normal

Howard Kim

May 02, 2025

2023 Jeep Gladiator

Open

NormalWashboard

Wanted to drive it during sundown as I had heard it’s great. Super easy drive. Some pockets of sugar sand and washboard areas from track vehicles. Many parts were beautiful to drive past, then you start to see pockets of development and heavy earth movers revealing what the area will change to eventually. I’d say if you haven’t done it yet go before it all gets developed. I recommend the Sunset, I stopped at a high point and just enjoyed the view and chilled after work. ^^v

Jon W

Dec 15, 2024

Open

Layne Smith

Nov 20, 2024

Open

Normal

Open, mostly well maintained dry dirt road. Mostly agricultural land, but rapidly being encroached with housing developments. North end is flooded as reported earlier. Would have waded through if not by myself, but open gates through the adjacent new housing developments got me back to pavement.

5 Mile Road Winter Garden - Clermont Trail can be accessed by the following ride types:

Single Track
50 Inch
60 Inch
High Clearance
Full Width

Access Description

The road is open to the public and does not require any permits or fees. Parts of the surrounding area are experiencing rapid residential development, so drivers should respect private property boundaries along the agricultural fields. The road is shared with runners, cyclists, and local farm machinery, so exercising caution and maintaining a low speed is recommended.