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Routes
Hikes
United States
Maine
Cumberland County

Oak Hill

Easy hikes and walks around Oak Hill

4.5

(20)

599

hikers

73

hikes

Hiking around Oak Hill offers a variety of easy trails through diverse landscapes. The area features woodlands, coastal paths, and park trails, providing accessible options for outdoor activity. These routes often traverse gentle terrain, making them suitable for casual walks and family outings. The natural setting includes wooded areas and stretches along beaches, offering varied scenery.

Best easy hiking trails around Oak Hill

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

Last updated: May 2, 2026

5

hikers

#1.

Winnick Woods Long Loop

5.94km

01:34

50m

50m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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1

hikers

1.56km

00:25

20m

10m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

1

hikers

2.13km

00:34

20m

20m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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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.

1

0

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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0

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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0

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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oliviakellis
November 18, 2023, Hinckley Park

With 40 acres, two scenic ponds and stunning fall foliage, Hinckley Park is a charming corner just outside of South Portland.

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Frequently Asked Questions

How many easy hiking trails are available around Oak Hill?

There are over 60 easy hiking trails around Oak Hill, offering a variety of options for casual walks and family outings. In total, the area features over 80 routes for hiking.

What kind of terrain can I expect on easy hikes around Oak Hill?

The easy hikes around Oak Hill feature diverse terrain, including peaceful woodlands, scenic coastal paths, and well-maintained park trails. While many routes are gentle, some may include uneven ground with roots or rocks, especially in wooded areas. For example, the Winnick Woods Long Loop explores wooded areas with minimal elevation gain, while Pine Point, Grand, and Surfside Beaches offers sandy coastal stretches.

Are there any short, easy walks suitable for a quick outing?

Yes, if you're looking for a shorter walk, the Winnick Woods Loop is a great option. It's about 1.0 mile (1.6 km) long and can typically be completed in under half an hour, leading through pleasant woodlands.

Are there any circular easy walks around Oak Hill?

Many of the easy trails around Oak Hill are designed as loops, providing a convenient circular walking experience. The Winnick Woods Long Loop and the Winnick Woods Loop are excellent examples of circular routes that allow you to explore the natural beauty without retracing your steps.

What do other hikers say about the easy trails in Oak Hill?

The easy trails in Oak Hill are highly regarded by the komoot community, with an average rating of 4.6 stars from over 20 reviews. Hikers often praise the varied scenery, from quiet woodlands to beautiful coastal views, and the accessibility of the routes for different ability levels.

Are there any scenic viewpoints or natural features on the easy trails?

Absolutely! The easy trails around Oak Hill offer several scenic spots. For coastal vistas, the Pine Point, Grand, and Surfside Beaches route provides stunning views along the coastline. In wooded areas, you can enjoy the natural beauty of forests and meadows, and some trails might reveal clues of past agricultural use, like old fencerow edges.

Can I find any interesting landmarks or attractions near the easy hiking trails?

Yes, the Oak Hill area is close to several interesting 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 bustling Portland Harbor.

Are there any easy trails that offer coastal views?

Yes, the Pine Point, Grand, and Surfside Beaches trail is an excellent choice for coastal views. This easy path offers picturesque scenery along the coastline and sandy beaches, perfect for a refreshing walk by the water.

Are the easy hiking trails around Oak Hill suitable for families with children?

Many of the easy hiking trails around Oak Hill are very suitable for families with children. The gentle terrain, minimal elevation gain, and varied scenery make them enjoyable for all ages. Routes like the Winnick Woods Loop are particularly good for shorter family outings.

Can I bring my dog on the easy hiking trails?

While many outdoor areas are dog-friendly, specific regulations can vary by trail or park. It's always best to check local signage or park websites for the most current rules regarding dogs on trails in the Oak Hill area. Generally, if dogs are permitted, they should be kept on a leash.

What is the best time of year to enjoy easy hikes in Oak Hill?

The best time to enjoy easy hikes in Oak Hill largely depends on your preference. Spring and fall offer pleasant temperatures and beautiful foliage. Summer is ideal for coastal walks, though trails can be busier. Even in winter, some trails are suitable for snowshoeing or cross-country skiing, offering a different kind of beauty, but always check conditions beforehand.

Are there options for parking near the easy hiking trails?

Parking availability varies by trailhead. Many popular trailheads, especially those within parks or conservation areas, typically offer designated parking lots. For specific routes, it's advisable to check the route details on komoot or local park information for parking instructions before you go.

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