4.7
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1,505
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197
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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 us an insider's view of what makes a great hike. We've sifted through the data to bring you a curated shortlist of the best hikes in Cumberland County, saving you the legwork and pointing you straight to the trails that deliver.
Hiking in Cumberland County, Maine, is all about embracing the coast. Expect a delightful mix of coastal scenery, peaceful woodland paths, and serene lakeside trails. The terrain is generally gentle, with easy to moderate routes dominating the landscape, making it accessible for many. You'll find yourself exploring nature preserves and state parks, with the Atlantic Ocean always a stone's throw away.
If you only do one hike, make it the Back Cove Trail. This 2.4 miles (3.8 km) easy loop is a local favorite for a reason, offering lovely waterfront views right in the heart of things. For a slightly different coastal experience, the Mackworth Island Trail, at 2.9 miles (4.7 km), is another top pick, providing beautiful ocean vistas and a refreshing sea breeze. With over 1,500 hikers having already explored these paths with komoot, you can trust these recommendations. Ready to discover your next favorite trail?
Last updated: May 11, 2026
5.0
(1)
36
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 67 feet (20 metres) of elevation gain, this hike is perfect for all skill levels, winding through mixed-growth forests and opening up to spectacular views of Casco Bay. You'll find charming surprises like the Fairy Village and Governor Baxter's Pet Cemetery, making it a unique and memorable outing.
Planning your visit is straightforward, but remember that Mackworth Island is a State Park, so a small entry fee is required. The trail's packed soil can get slippery when wet, and some areas have exposed tree roots, so wear appropriate footwear. While the main loop is quite accessible, some side paths to the shore are steeper. Consider visiting at low tide to fully explore the small, rocky beaches.
Beyond its scenic beauty, Mackworth Island is a legislated bird sanctuary, making it a prime spot for birdwatching. The island also holds historical significance with remnants of a Civil War-era granite pier and hosts the Maine Educational Center for the Deaf and Hard of Hearing. It's a place rich in natural beauty, history, and unique features that set it apart from other coastal walks.
25
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 pine and oak trees create a peaceful atmosphere, before emerging onto rocky shores and tidal marshes with expansive views of Casco Bay and the Harraseeket River. This easy 1.8-mile (3.0 km) hike, with just 135 feet (41 metres) of elevation gain, is a fantastic way to experience the region's diverse ecosystems in about 48 minutes.
Located within Wolfe's Neck Woods State Park, this trail is easily accessible and features amenities like restrooms and picnic areas. It's a dog friendly route, so bring your leashed companion along. If you're visiting in winter, be prepared for potentially icy conditions near the tidal zones, and consider wearing sturdy, waterproof boots.
What makes this trail truly special is its ability to provide a comprehensive overview of the park's unique blend of marine and terrestrial environments. Keep an eye out for wildlife; deer are often spotted near the marshes, and eagles and osprey are common sights soaring above the bay, especially between May and August. Interpretive signs along the path also offer insights into the local flora and fauna.

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5.0
(2)
10
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 dirt paths, rocky segments, and some steeper climbs, especially if you choose to ascend counterclockwise. The highlight is undoubtedly the panoramic views from the summit of Bald Pate Mountain, where you can take in the beauty of Peabody Pond, Foster Pond, and the broader Sebago Lake region.
This easy 3.2-mile (5.2 km) hiking loop, with 697 feet (212 metres) of elevation gain, typically takes around 1 hour and 39 minutes to complete. It's a great option for a half-day adventure. While specific parking information isn't detailed, arriving early is always a good strategy, especially during peak times, to ensure a spot at the Bald Pate Mountain Preserve trailhead.
Known as one of the most scenic routes within the Bald Pate Mountain Preserve, this trail is a local favorite for its high-payoff views. It's an excellent choice if you're looking for a hike that feels substantial but is still manageable for most fitness levels, offering a taste of Maine's beautiful lake and mountain scenery.
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 dirt paths, forest floor, and even some woodchips, encountering roots, rocks, and narrow bridge crossings. Keep an eye out for several small waterfalls, especially during the wetter seasons, and impressive large white pine trees that add to the natural beauty of the area.
This easy 4.3-mile (6.9 km) hiking route involves a modest 436 feet (133 metres) of elevation gain and typically takes around 1 hour and 56 minutes to complete. Parking is available at the Blackstrap Road parking lot, which serves as a convenient starting point. Be aware that deer ticks are prevalent, so remember to check yourself thoroughly after your hike, and consider wearing blaze orange if visiting during hunting season.
Part of a larger trail network, the Blackstrap Hill River Loop is notable for its excellent river access and diverse wildlife habitat, including deer, beaver, and various bird species. The trails are generally well-maintained and clearly marked, often with maps at intersections, making it easy to navigate. It's a great option for those seeking a family-friendly hike or a peaceful natural escape.
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 the rugged beauty of Kettle Cove, with opportunities to spot small sea creatures in the tide pools. This easy 3.2-mile (5.2 km) hike, with just 68 feet (21 metres) of elevation gain, provides a diverse and scenic experience that takes approximately 1 hour and 20 minutes to complete.
Planning your visit is straightforward for this popular Maine coast trail. Dogs are permitted on leash during the off-season, from October 1 to March 31, making it a great option for a winter or shoulder-season walk with your canine companion. Consider timing your visit for the late afternoon to catch the beautiful sunsets over Crescent Beach, adding an extra layer of magic to your outing.
What makes this route truly stand out is its ability to pack so much varied coastal landscape into one accessible loop, connecting Crescent Beach State Park and Kettle Cove State Park. Beyond the stunning ocean vistas, keep an eye out for monarch butterflies in the mowed meadows during late summer and fall, and a variety of bird species year-round. It's a beloved spot for both locals and tourists, offering a peaceful escape, especially outside of peak season.
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 diverse flora like various berries and ferns, and might even spot wildlife such as red-tailed hawks. Elevated bridges and wooden boardwalks make navigating the marshy areas easy, creating a tranquil escape in southern Maine.
Accessing the trail is simple, with a small gravel parking area for about eight vehicles and a map kiosk at the trailhead off Sawyer Road. While the trail is generally easy, some sections have moderate grades and occasional craggy outcrops. It's a popular multi-use trail, so you'll share it with hikers, trail runners, dog walkers, and mountain bikers. Using a navigation app is recommended due to the trail's many twists and turns.
Winnick Woods is a 71-acre parcel that forms a vital part of the Cape Elizabeth Greenbelt, connecting to other systems like the Cross Hill Trails. This connectivity allows for longer, interconnected hikes if you wish to extend your adventure beyond the 3.7 miles (5.9 km) of this easy loop. The land was donated for preservation, honoring the Winnick family, and showcases southern Maine's diverse forest ecosystems.
7
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 it a fantastic choice for a relaxed outing where you can spot everything from massive cruise ships to vintage trains of the Maine Narrow Gauge Railroad. You'll find plenty of spots to pause and soak in the scenery, especially around East End Beach or Fish Point.
Planning your visit is straightforward for this easy 2.3-mile (3.7 km) hike, which takes about 57 minutes with only 48 feet (15 metres) of elevation gain. It's a popular destination, so consider an early start for easier parking. The trail is well-equipped with benches and picnic tables, and it's both family-friendly and dog-friendly, with specific off-leash areas available.
More than just a scenic walk, the Eastern Promenade Trail is part of a larger historic landscape designed by the renowned Olmsted Brothers firm. It's also a segment of the East Coast Greenway, connecting to other popular Portland trails like the Back Cove Trail for those looking to extend their adventure. This trail is a true recreational hub, perfect for a quick, rewarding dose of coastal beauty and history.
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 Pond. This easy 4.2-mile (6.7 km) hike, with its gentle 379 feet (116 metres) of elevation gain, provides a refreshing escape into nature, taking about 1 hour and 50 minutes to complete. You'll encounter a mix of wide, gravel paths and narrower, more technical sections, with rewarding views of the White Mountains from spots like Atherton Hill. It's a great option if you're seeking varied terrain and scenic overlooks without an overly strenuous climb.
Planning your visit to the East Windham Conservation Area is straightforward, as it's a multi-use area open year-round for activities like hiking, mountain biking, and even winter sports. Parking is available at the trailhead, and there are no permits or fees required to access the trails. While some sections are being upgraded for universal accessibility by 2025, the current network offers a range of experiences from easy to moderate, making it a flexible choice for different skill levels.
This trail system is part of a much larger 30-mile interconnected network, linking to other preserves and forming a significant 2,000-acre conservation corridor in Greater Portland. The 700-acre East Windham Conservation Area itself, conserved in 2023, is notable for its size and ecological importance, providing crucial wildlife habitat and clean water. It's an excellent choice if you appreciate a well-maintained trail system with a strong conservation story and the potential for extended adventures.
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 about 1 hour and 1 minute. This route meanders around the uniquely shaped Florida Lake, guiding you through wetlands and mature forests. You'll encounter bog bridges and boardwalks designed to navigate the often-muddy terrain, making it a delightful experience for families and those new to hiking.
Planning your visit means being ready for potentially wet conditions; waterproof boots are a good idea, especially during spring or after heavy rain. The trail is known for its abundant wildlife, so bring binoculars for birdwatching. While specific parking information isn't detailed, the trail's easy difficulty and short duration make it a convenient option for a quick outdoor adventure.
This loop is a true hidden gem for wildlife enthusiasts, providing excellent habitat for waterfowl, bald eagles, and even larger mammals like beaver and deer. The presence of vernal pools adds another layer of ecological interest, hosting unique amphibian populations. It's a fantastic opportunity to immerse yourself in Maine's natural beauty and observe diverse flora like skunk cabbage and princess pine.
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 of stone dust and pavement, passing by horticultural gardens and offering excellent opportunities for birding, with sightings of great blue herons and mallards. It's a gentle, tree-lined loop that feels surprisingly natural despite its city location.
Planning your visit is straightforward for this popular route. The trail is easily accessible, with amenities like benches, seasonal water fountains, and portable toilets available in parking areas such as Preble Street Extension and Payson Park. This easy 2.4-mile (3.8 km) loop, with just 17 feet (5 metres) of elevation gain, takes approximately 57 minutes, making it ideal for a quick stroll or a leisurely outing at any time of day.
This historic multi-use pathway, completed in 1917, is one of Portland's oldest and most cherished trails, connecting to other prominent routes like the Bayside Trail and Eastern Promenade Trail under Tukey's Bridge. It's a fantastic option for families and dog owners, providing a low-difficulty experience that highlights the natural beauty and wildlife of the urban estuary habitat.
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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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