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MTB trails
United States
Maine
Cumberland County

Oak Hill

The best MTB trails around Oak Hill

5.0

(6)

155

riders

13

rides

Mountain biking around Oak Hill offers diverse terrain, from flowing singletrack to packed gravel fire roads. The landscape features varied elevation changes, including significant climbs and descents, alongside scenic river paths and forested areas. Riders can explore a mix of technical sections, boardwalk bridges, and open trails, often within natural forest settings. This region provides a range of mountain bike routes suitable for different skill levels.

Best mountain bike trails around Oak Hill

  • The most popular mountain bike trail is…

Last updated: September 4, 2026

10

riders

#1.

Winnick Woods Greenbelt Trails – Winnick Woods loop from South Portland

30.1km

02:13

200m

200m

Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.

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Moderate

Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.

Easy
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6

riders

Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.

Easy

5.0

(3)

8

riders

Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.

Easy

Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.

Moderate
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Tips from the Community

Lisa
May 30, 2025, Cross Hill Trails

You'll find several miles of trails here, blending seamlessly into the trails of Winnick Woods, just to the north. If you're walking, watch out for fast-moving mountain bikers on some of the Winnick Woods trails.

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Lisa
May 30, 2025, Winnick Woods

This 71-acre parcel of woodland was donated to the township of Cape Elizabeth. It's a popular spot for walking, jogging and biking, and contains a 1.7-mile multi-use loop trail. There are also some trails that were purpose-built for mountain biking, so watch out for fast-moving bikers on those.

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DiPietros Market is a South Portland classic. It is a great place to stop for a break during a long ride for a sandwich or cold drink.

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Hans
August 28, 2024, Scarborough Marsh

Very large salt marsh. Great for bird watching

Translated by Google

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Hubert Trapp
August 26, 2024, Jewell Falls

The 'Jewel Falls' is a natural waterfall in Portland's 'Fore River Sanctuary'. The waterfall is located on the 'Portland Trails' network in the nature reserve. At the end of May 2024, the water will only flow as a trickle over the rocks down into the wetland. https://www.newenglandwaterfalls.com/me-jewellfalls.html

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Anette
February 15, 2024, Jewell Falls

The picturesque Jewell Falls, with its two main steps and small cascades, are the only natural waterfalls in Portland. They are accessible through the Portland Trail System trails, and you'll quickly forget that you're in the city.

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mtm05005
February 14, 2024, Back Cove Trail

The Back Cove Trail is one of the oldest and most popular trails in Portland. As the name suggests, it encircles Back Cove.

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Looking east there are wonderful views out into nature and the expansive Saco River. Looking west on the other hand and it's a look back into the industrial history of the area. Mills line both river banks, designated as the Biddeford–Saco Mills Historic District.

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Frequently Asked Questions

How many mountain bike trails are available in Oak Hill?

Oak Hill offers a diverse network of over 15 mountain bike trails. These routes cater to various skill levels, from easy loops to more challenging singletrack.

What kind of terrain can I expect on mountain bike trails in Oak Hill?

The terrain in Oak Hill is quite varied. You'll find flowing singletrack, packed gravel fire roads, and doubletrack. Some areas feature tight and twisty climbs, boardwalk bridges, and even water crossings, while others offer significant elevation changes and forested paths. For example, trails in the Wisconsin area feature scenic routes along the Menomonee River, while Hanover offers a mix of beginner-friendly ski trails and advanced singletrack.

Are there easy mountain bike trails suitable for beginners in Oak Hill?

Yes, Oak Hill has several easy mountain bike trails perfect for beginners. For instance, the Winnick Woods Greenbelt Trails – Winnick Woods loop from Dow's Woods Nature Preserve is an accessible 7.2-mile path. The Morganton, North Carolina area is also developing a significant trail system with 5 miles of beginner-friendly trails, expanding to 9 miles soon.

Are there any challenging mountain bike trails in Oak Hill?

Yes, for riders seeking a challenge, Oak Hill offers moderate trails with varied terrain and elevation gain. The Winnick Woods Greenbelt Trails – Winnick Woods loop from South Portland is a 18.7-mile moderate trail with notable elevation. The Hanover area also includes more advanced singletrack options like Crystal Ridge, Junji, and Flow, with a total vertical of 753 feet.

Can I find mountain bike trails that are loop routes in Oak Hill?

Absolutely. Many of the mountain bike trails in Oak Hill are designed as loops, providing a convenient way to explore the area. Examples include the Back Cove Trail – Canco Woods loop from Portland and the Jewell Falls loop from Portland.

What natural features or attractions can I see along the mountain bike trails in Oak Hill?

Oak Hill's trails often pass by scenic natural features and attractions. You might encounter river paths, forested areas, and even boardwalk bridges. In the Littleton, Massachusetts area, notable natural attractions include Outlook Rock and Tophet Chasm. Near Portland, you can explore highlights like East End Beach, the Back Cove Trail, and Deering Oaks Park.

Are there any scenic viewpoints on the mountain bike trails in Oak Hill?

Yes, several Oak Hill locations offer scenic viewpoints. For example, the Loudon area features trails with significant elevation gain, such as Tower Trail, which provides vistas of the surrounding natural beauty. You can also enjoy Views of Casco Bay from certain points near the trails.

What do other mountain bikers enjoy most about mountain biking in Oak Hill?

The mountain biking experience in Oak Hill is highly rated by the komoot community, with an average score of 5.0 stars. Riders often praise the diverse terrain, from flowing singletrack to varied elevation changes, and the natural forest settings that define the region. The network offers options for different ability levels, making it enjoyable for many.

Are there mountain bike trails that pass by waterfalls in Oak Hill?

Yes, you can find trails that lead to waterfalls. The Stroudwater Trail – Jewell Falls loop from Fore River Sanctuary is an easy route that includes the scenic Jewell Falls.

What is the best time of year to go mountain biking in Oak Hill?

Oak Hill offers varied conditions depending on the season and specific location. Generally, spring through fall provides the most favorable weather for mountain biking. Some areas, like Hanover, might have trails that are also used for skiing, suggesting a distinct winter season. It's always a good idea to check local trail conditions before heading out.

Is public transport available to access mountain bike trails in Oak Hill?

While specific public transport options vary by the exact Oak Hill location, many trail systems are designed with accessibility in mind. For trails around urban centers like Portland, public transport might be an option to get closer to trailheads. It's recommended to check local transit schedules for the specific area you plan to visit.

Are there any places to explore near the mountain bike trails in Oak Hill?

Yes, there are several interesting places to explore near the mountain bike trails. You can visit landmarks like Portland Head Light at Fort Williams Park or enjoy the vibrant atmosphere of Portland Harbor. For more natural exploration, consider Robinson Woods or the South Portland Greenbelt.

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