The best family-friendly hikes and walks in Cumberland County
4.8
(93)
1,525
hikers
104
hikes
Family friendly hiking trails in Cumberland County traverse a diverse landscape, characterized by coastal paths, dense woodlands, and varied topography. The region features gentle elevations and numerous waterways, providing accessible outdoor experiences. These physical features contribute to a wide range of hiking opportunities suitable for families.
Best family friendly hiking trails in Cumberland County
- The most popular family friendly hiking route is Mackworth Island Trail, a 2.9 miles (4.7 km) trail that takes 1 hour 13 minutes to complete.…
Last updated: May 10, 2026
5.0
(1)
36
hikers
4.75km
01:13
20m
30m
Embark on an easy hike along the Mackworth Island Trail, a delightful loop offering continuous views of Casco Bay. This 2.9-mile (4.7 km) route features diverse scenery, from heavily wooded…
7
hikers
5.23km
01:20
20m
20m
Lace up for an easy hike on the Kettle Cove and Crescent Beach Loop, a coastal route spanning 3.2 miles (5.2 km). This trail offers a gentle experience with only…
Sign up for free
5
hikers
5.94km
01:34
50m
50m
Embark on the Winnick Woods Long Loop, an easy 3.7-mile (5.9 km) hike that takes you through varied landscapes in Cape Elizabeth. You will gain 157 feet (48 metres) in…
6
hikers
3.72km
00:57
10m
20m
Enjoy an easy hike along the Eastern Promenade Trail, a paved multi-use path that offers continuous views of Casco Bay and its islands. This route covers 2.3 miles (3.7 km)…
4
hikers
3.81km
00:58
10m
10m
Embark on an easy hike along the Back Cove Trail, a popular route that offers a refreshing escape with scenic views. This 2.4-mile (3.8 km) loop features a mostly flat…
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Popular around Cumberland County
Family-friendly hikes around Portland
Family-friendly hikes in Kettle Cove State Park
Family-friendly hikes in Crescent Beach State Park
Family-friendly hikes in Scarborough Beach State Park
Family-friendly hikes around Sebago Lake
Family-friendly hikes around Brunswick
Family-friendly hikes around South Portland
Family-friendly hikes around Yarmouth
On the trail of the Pilgrim Fathers – road trip along the Atlantic coast
Other adventures in Cumberland County
Tips from the Community
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.
0
0
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
A place with a nice overlook. Good to have a short stop.
0
0
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/
2
0
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
1
0
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/
2
0
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.
0
0
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.
0
0
Frequently Asked Questions
How many family-friendly hiking trails are available in Cumberland County?
Cumberland County offers over 100 family-friendly hiking trails, providing a wide variety of options for all ages and skill levels. The majority of these, around 80, are rated as easy, making them perfect for a relaxed family outing.
What is the general difficulty level of family-friendly hikes in Cumberland County?
Most of the family-friendly hikes in Cumberland County are rated as easy. These trails are generally well-maintained with gentle inclines, making them suitable for young children and those new to hiking. There are also some moderate options for families looking for a bit more of a challenge.
Are there any easy, flat trails suitable for young children or strollers?
Yes, Cumberland County has several easy, relatively flat trails perfect for families with young children or strollers. The Back Cove Trail is a great example, offering minimal elevation change. Additionally, the Cumberland Valley Rail Trail in Pennsylvania offers a flat, accessible option, and the LeTort Spring Run and Nature Trail is known for its accessible paths near Carlisle.
Can we find family-friendly hikes with waterfalls in Cumberland County?
Absolutely! Cumberland County boasts several beautiful waterfalls that are accessible via family-friendly trails. In Pennsylvania, you might find smaller cascades, while in Tennessee, areas like Ozone Falls State Natural Area and Fall Creek Falls State Park offer impressive sights. Within our guide, you can explore highlights like Jewell Falls and Steep Falls Waterfall.
Are there trails with scenic views or overlooks suitable for families?
Yes, many family-friendly trails in Cumberland County lead to rewarding scenic views. For instance, the Mackworth Island Trail offers beautiful coastal vistas. In the broader region, you can find overlooks like the View from Bradbury Mountain Summit, and the Black Mountain Overlook in Tennessee provides panoramic views of the Tennessee Valley.
What do other hikers say about family-friendly trails in Cumberland County?
The komoot community highly rates the family-friendly trails in Cumberland County, with an average score of 4.8 out of 5 stars. Reviewers often praise the well-maintained paths, diverse scenery, and the accessibility of many routes for families with children.
Are there any circular family walks in Cumberland County?
Yes, many family-friendly routes in Cumberland County are designed as circular walks, allowing you to start and end at the same point without retracing your steps. The Winnick Woods Long Loop is a great example of a circular trail suitable for families.
Can I bring my dog on family-friendly hikes in Cumberland County?
Many trails in Cumberland County are dog-friendly, but it's always best to check specific park or trail regulations before you go. Generally, dogs are welcome on a leash. For example, the Kettle Cove and Crescent Beach Loop is a popular choice for families with canine companions.
What natural attractions can we explore on family hikes in Cumberland County?
Beyond waterfalls and scenic views, family hikes in Cumberland County offer a chance to explore diverse natural attractions. You can visit coastal areas like Crescent Beach State Park and East End Beach, or explore serene woodlands and preserves such as the Fore River Sanctuary. The region's varied landscapes include lakes, forests, and unique rock formations.
Are there any interesting landmarks or points of interest along these family trails?
Yes, Cumberland County is rich in both natural and historical landmarks. Along the trails, you might encounter lighthouses like Portland Head Light at Fort Williams Park, or enjoy the bustling atmosphere of Portland Harbor. Many trails also offer insights into the region's natural beauty and history.
What is the best time of year for family hikes in Cumberland County?
Spring, summer, and fall all offer wonderful conditions for family hikes in Cumberland County. Spring brings blooming wildflowers, summer provides lush greenery and warmer temperatures for water activities, and fall showcases stunning foliage. Winter hikes can also be beautiful, especially on well-maintained trails, but require appropriate gear for colder weather.
Are there any permits needed for hiking with kids in Cumberland County?
For most general hiking trails in Cumberland County, permits are not required for day use. However, if you plan to visit specific state parks or engage in activities like camping, it's always a good idea to check the park's official website for any specific requirements or fees. For more information on outdoor recreation in the Pennsylvania part of the county, you can visit cumberlandcountypa.gov.
Most popular routes in Cumberland County
Most popular attractions in Cumberland County
Get inspired with the komoot mobile app
Didn’t find what you were looking for?
Check out more Hikes throughout Cumberland County below and find the perfect route in your destination.
Explore more
Browse the best Hikes in other regions.
