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Hikes
United States
Maine
Cumberland County

Oak Hill

The best walks and hikes around Oak Hill

4.4

(20)

603

hikers

81

hikes

Hiking around Oak Hill offers diverse landscapes, characterized by woodlands, open meadows, and proximity to water features including ponds and coastal areas. The region features varied terrain, from gentle paths to routes with slight elevation changes. These natural features provide opportunities for wildlife observation and scenic appreciation. The area's trail network includes paths suitable for various fitness levels.

Best hiking trails around Oak Hill

  • The most popular hiking route is Winnick Woods Long Loop, a 3.7 miles (5.9 km)…

Last updated: June 29, 2026

6

hikers

#1.

Winnick Woods Long Loop

5.94km

01:34

50m

50m

The Winnick Woods Long Loop offers a delightful journey through varied terrain, from classic wooded paths to a large open meadow, past extensive wetlands, and a small pond. You'll encounter…

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Easy

3

hikers

14.9km

03:52

100m

100m

Embark on a moderate hike along the Stroudwater Trail, a 9.2 miles (14.9 km) route that offers continuous views of the winding Stroudwater River. You will experience a densely wooded…

Moderate
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Explore the scenic coastline on the Pine Point, Grand, and Surfside Beaches trail, an easy 3.6-mile (5.8 km) hike. You will experience long stretches of packed sand with continuous ocean…

Easy

1

hikers

1.56km

00:25

20m

10m

Embark on the Winnick Woods Loop for an easy hike through diverse landscapes. This tranquil route winds through dense woodlands, open meadows, and extensive wetlands, offering a refreshing outdoor experience.…

Easy

Hike the easy 1.1-mile Lucy R. Sprague Memorial Trail through diverse woodlands and wetlands to an observation deck with views of Libby Rive

Easy
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Popular around Oak Hill

Cycling around Oak Hill

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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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Lisa
January 25, 2024, Short Pond

Together, this little pond and the longer pond to the north — unsurprisingly called Long Pond — are called the Ferry Beach ponds, due to their proximity to the beach of the same name.

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oliviakellis
December 17, 2023, Surfside Beach

Surfside Beach, lies along a 7-mile expanse between the Scarborough and Saco rivers. While running, witness the impressive maneuvers of surfers on the waves. With a lively summer scene and numerous eateries and shops, it offers a delightful backdrop for your run

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Andrus
December 4, 2023, Surfside Beach

Surfside is located along a 7-mile stretch of beaches between the Scarborough & Saco rivers. The area is quite popular during the summer and you'll find any number of restaurants, bars, cafes, & shops to stop at. It can be a challenge to find parking so riding here is a great option.

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Jamie S.
November 26, 2023, Old Orchard Pier

The Old Orchard Pier is a landmark in the small beach town of Old Orchard Beach, Maine. This historic wooden pier juts out over 600 feet over the ocean and has rides, great local restaurants, souvenir shops, and views over the beach and Atlantic Ocean.

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Frequently Asked Questions

How many hiking trails are available around Oak Hill?

There are over 80 hiking routes in the Oak Hill area, offering a wide range of experiences. These trails traverse diverse landscapes, including woodlands, open meadows, and coastal paths, catering to various preferences and fitness levels.

What kind of difficulty levels can I expect on the hiking trails in Oak Hill?

The majority of hiking trails in Oak Hill are classified as easy, with 66 routes suitable for casual strolls. There are also 14 moderate trails for those seeking a bit more challenge. Currently, there are no difficult routes listed, making the area very accessible for most hikers.

Are there family-friendly hiking options in Oak Hill?

Yes, Oak Hill offers numerous family-friendly hiking options, primarily consisting of easy trails through woodlands and meadows. These paths are generally well-suited for all ages, providing opportunities for nature observation in a safe environment. Many routes feature gentle ascents and flat terrain, perfect for a leisurely family outing.

Can I bring my dog on the hiking trails in Oak Hill?

Many trails in Oak Hill are dog-friendly, allowing you to enjoy the natural beauty with your canine companion. It's always recommended to keep dogs on a leash and to check specific trail regulations or signage at trailheads, as rules can vary. The varied terrain, from forests to coastal areas, provides plenty of interesting smells and sights for dogs.

Are there any circular hiking routes in Oak Hill?

Yes, Oak Hill features several circular hiking routes. For example, the Winnick Woods Long Loop is a popular 3.7-mile (5.9 km) option that takes you through beautiful wooded areas. Another shorter circular option is the Winnick Woods Loop, which is 1.0 mile (1.6 km) and also explores the woodlands.

What natural features can I expect to see while hiking in Oak Hill?

Oak Hill's hiking trails showcase a variety of natural features. You'll encounter extensive forests and woodlands, open meadows, and significant water features like ponds and coastal areas. Some locations also boast dramatic topography and scenic vistas, offering diverse landscapes for exploration and wildlife observation.

Are there any interesting landmarks or attractions near the hiking trails?

Yes, the Oak Hill area is close to several interesting landmarks and attractions. You can explore coastal highlights like East End Beach and enjoy Views of Casco Bay. Other notable spots include the iconic Portland Head Light at Fort Williams Park and the scenic Portland Harbor.

What do other hikers enjoy the most about hiking in Oak Hill?

The hiking experience in Oak Hill is highly rated by the komoot community, with an average score of 4.6 stars from over 20 reviews. Hikers often praise the diverse terrain, from tranquil woodlands to refreshing coastal paths, and the accessibility of trails for various fitness levels. The opportunities for wildlife observation and scenic appreciation are also frequently highlighted.

Are there any coastal hiking trails in Oak Hill?

Yes, Oak Hill offers beautiful coastal hiking opportunities. A prime example is the Pine Point, Grand, and Surfside Beaches route, an easy 3.6-mile (5.8 km) path that provides flat terrain along the scenic coastline, perfect for a refreshing walk by the sea.

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

Oak Hill offers enjoyable hiking experiences across multiple seasons. Spring and fall provide pleasant temperatures and vibrant foliage, while summer is ideal for coastal walks and enjoying the meadows. Even winter can be beautiful for hiking, especially in forested areas, though some trails might require appropriate gear for snow or ice.

Are there opportunities for birdwatching or wildlife observation?

Absolutely. The diverse habitats in Oak Hill, including forests, meadows, and wetlands, make it an excellent spot for birdwatching and wildlife observation. Ponds and coastal areas attract various bird species, and you might spot deer or other local wildlife, particularly in quieter woodland sections.

Where can I find parking for trailheads in Oak Hill?

Parking availability varies by specific trailhead. Many popular hiking areas in Oak Hill, such as those near parks and conservation areas, typically offer designated parking lots. It's advisable to check the specific route details on komoot or local park websites for precise parking information before your visit.

Are there any longer, more challenging hikes available?

While the majority of trails are easy, Oak Hill does offer moderate options for those looking for a longer hike. The Stroudwater Trail, for instance, is a moderate 9.2-mile (14.9 km) route with some elevation changes, providing a more extended and engaging experience through varied landscapes.

Most popular routes around Oak Hill

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