4.7
(93)
1,505
hikers
197
hikes
If you've ever tried to plan hiking in Cumberland County, you know how quickly the options can feel overwhelming. With so many trails to choose from, it's tough to tell which routes are genuinely worth your time and effort, and which are just filler. You want the highlights, the trails that truly capture the essence of the region, without all the guesswork.
That's where we come in. Our komoot community has explored, mapped, and reviewed hundreds of routes here, giving…
Last updated: May 11, 2026
5.0
(1)
39
hikers
4.75km
01:13
20m
30m
The Mackworth Island Trail offers a delightful escape into coastal Maine, providing an easy 2.9-mile (4.7 km) loop that takes about 1 hour and 13 minutes to complete. With only…
5.0
(1)
27
hikers
2.96km
00:48
40m
40m
The Harraseeket and White Pines Trail Loop offers a delightful ramble through coastal Maine, showcasing a rich tapestry of natural beauty. You'll traverse through dense coastal woods, where towering white…

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5.0
(2)
11
hikers
5.22km
01:39
210m
190m
The South Face Loop Trail on Bald Pate Mountain offers a fantastic blend of effort and reward, guiding you through varied terrain to stunning overlooks. You'll navigate a mix of…
7
hikers
6.93km
01:56
130m
140m
The Blackstrap Hill River Loop offers a delightful journey through diverse forests and along the scenic West Branch of the Piscataqua River in Falmouth, Maine. You'll traverse a mix of…
7
hikers
5.23km
01:20
20m
20m
The Kettle Cove and Crescent Beach Loop offers a delightful coastal ramble, seamlessly blending sandy beaches, rocky coves, and tranquil meadows. You'll experience the expansive, mile-long Crescent Beach before exploring…
6
hikers
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…
8
hikers
3.72km
00:57
10m
20m
The Eastern Promenade Trail offers a delightful escape along Portland's waterfront, providing constant, expansive views of Casco Bay and its islands. This mostly paved, multi-use path is incredibly accessible, making…
5
hikers
6.70km
01:50
120m
90m
The East Windham Purple and Blue Trail Loop offers a delightful exploration of the East Windham Conservation Area, winding through lush forests and along the serene shorefront of Little Duck…
4
hikers
4.01km
01:01
10m
10m
If you're seeking a tranquil nature escape in Maine, the Florida Lake Loop offers an easy 2.5-mile (4.0 km) hike with just 44 feet (13 metres) of elevation gain, taking…
4
hikers
3.81km
00:58
10m
10m
The Back Cove Trail offers a refreshing urban escape, circling the tidal basin with continuous views of the Portland skyline and harbor. You'll find yourself on a mostly flat path…
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Popular around Cumberland County
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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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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A place with a nice overlook. Good to have a short stop.
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The Maine Narrow Gauge Railroad Co. & Museum has maintained a narrow gauge railway since 1993, which runs approximately 2.4 km along the coast of the Portland Peninsula and parallel to the Eastern Promenade Trail. The railway tracks date from a time when the Atlantic & St. Lawrence Railroad and later the Grand Trunk Railroad ran from Portland to Montreal. After the East End Rail Bridge was badly damaged by fire in 1984 and was not repaired for economic reasons, the railway line was no longer used. This led to the founding of the non-profit organization with the aim of preserving the railway and making its history unforgettable. https://mainenarrowgauge.org/
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The gigantic military fortress Battery Steele was built during World War II to house heavy guns to protect the North Atlantic fleet. After the war, the site came into the possession of the Casco Bay Island Development Association and later the Star Foundation, a non-profit organization, became the owner of the fortress. When Battery Steele was put up for sale again, a grassroots campaign was launched by a group of islanders. In 1995, the group bought the 5.5-hectare property to preserve it as a recreational and historical site. This is how Peaks Island Land Preserve, a volunteer organization, was created. In 2005, Battery Steele was added to the National Register of Historic Places. Walking through the more than 100-meter-long dark tunnel inside Battery Steele creates indescribable impressions. The walls are covered in graffiti, many of which unfortunately do not claim to be classified as ‘street art’. https://www.peaksislandlandpreserve.org/battery-steele
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The Atlantic bay off Portland is called 'Casco Bay'. The approximately 520 sq km bay is part of the Gulf of Maine and lies between Cape Elizabeth south of Portland and Cape Small, a peninsula in eastern Maine that extends far into the Atlantic. Six inhabited islands lie in the bay and can be reached by ferry all year round. You can find detailed information about the bay on the website of the 'Friends of Casco Bay - Casco BAYKEEPER'. https://www.cascobay.org/casco-bay/
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Crescent Beach State Park is a classic sandy Maine beach. The park has sand dunes, picnic areas and great views of an offshore island and the ocean.
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East End Beach backs up to Eastern Promenade, which is one of Portland's most popular waterfront parks. The paved path following the shore line is a great trail to use for accessing this beach area.
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Yes, there are over 100 hiking routes to explore. The terrain is quite varied, with the majority being easy, flat coastal paths and woodland trails, but there are also a number of more moderate routes with some elevation.
The area is highly rated by the komoot community, with an average score of 4.6 stars. Hikers often praise the beautiful mix of coastal scenery and quiet, well-maintained woodland paths.
Absolutely. The region is great for families. For an easy, flat walk, consider the Cherry Hills Trail – Cherry Hills Farm, Gorham. It's a pleasant 2.6-mile (4.2 km) loop that's suitable for all ages.
Many trails in Cumberland County are dog-friendly, but policies can vary between parks and preserves. It's always best to keep your dog on a leash and check local signage. A good option to explore with your canine companion is the Pleasant Hill Preserve loop — Cape Elizabeth.
Yes, many of the best trails are loops, allowing you to enjoy a varied walk without retracing your steps. A great example is the Loop Trail – Hedgehog Mountain, Freeport, which offers a pleasant 2.9-mile (4.7 km) circuit through the woods.
For a route that features a waterfall, check out the Jewell Falls and Thompsons Point – Portland trail. Jewell Falls is Portland's only natural waterfall and a lovely feature of this walk.
For a beautiful walk alongside a lake, the Outer Loop – Sebago Lake State Park is an excellent choice. This nearly 4-mile (6.4 km) trail offers wonderful views of the water in a peaceful park setting.
While the region is known more for its gentle terrain, you can find some moderately challenging routes. The Bri-Mar Trail – Rattlesnake Mountain, Casco involves a climb with over 550 feet (170 m) of elevation gain, rewarding you with great views from the top.
If you're looking for a longer walk, the Robinson Woods Preserve & Fort Williams Park loop — Portland, Maine is a great option. It's a 6.2-mile (10 km) route that takes you through beautiful coastal forest.
Yes, for a gentle walk through open fields, the Fuller Farm Preserve loop via the Hayfield, Maine, and Bird Trails — Scarborough is perfect. It's a quiet, 1.9-mile (3.1 km) trail that's also excellent for birdwatching.
Coastal trails typically feature a mix of packed earth, some rocky sections, and occasional boardwalks. A great example is the Cliff Trail loop — Sebascodegan Island, which follows the shoreline and includes some short, steeper climbs through the woods, offering fantastic views of the water.
Yes, the Back Cove Trail loop — Portland, Maine is a very popular 3.6-mile (5.8 km) paved path. It's mostly flat and offers lovely views across the water, making it ideal for walking, jogging, and running.


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