4.5
(94)
2,937
riders
334
rides
Road cycling in Cumberland County features a diverse landscape, primarily characterized by its extensive coastline along the Atlantic Ocean and numerous bays. The region offers a network of paved routes that traverse coastal areas, providing views of the ocean and iconic lighthouses. Inland, routes often pass through forests, wetlands, and along the shores of lakes and rivers. The terrain generally includes rolling hills, with some routes offering moderate elevation changes.
Last updated: April 24, 2026
4.5
(2)
158
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
4.7
(3)
42
riders
31.0km
01:16
200m
200m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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3.0
(1)
22
riders
64.8km
02:54
430m
430m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
26
riders
57.1km
02:40
390m
390m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
19
riders
99.4km
04:20
630m
630m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
18
riders
110km
04:56
710m
710m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.0
(1)
17
riders
20.3km
01:00
100m
100m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
16
riders
17.2km
00:47
40m
40m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
8
riders
85.5km
03:47
610m
610m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
6
riders
36.0km
01:48
440m
440m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Cumberland County
Road Cycling Routes around Portland
Road Cycling Routes around South Portland
Road Cycling Routes around Westbrook
Road Cycling Routes around South Windham

Road Cycling Routes around Little Falls
Road Cycling Routes around Gorham
Road Cycling Routes around North Windham

Road Cycling Routes around Standish
Road Cycling Routes around Falmouth
Road Cycling Routes around Sebago Lake
The Portland Head Light is located on a rocky promontory in Cape Elizabeth, Maine, and has marked the entrance to Portland Harbor since 1791. It is the oldest lighthouse in the state. The 24-meter-tall, white tower structure was built at the direction of George Washington. Today, the U.S. Coast Guard operates the light, while the former keeper's house houses a museum. The building is owned by the municipality and is located in picturesque Fort Williams Park, overlooking the Atlantic Ocean.
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Pineland Farms is a unique area that features many miles of hiking trails, gardens, disc golf courses, a market cafe and bakery, restaurants, and some small businesses. The market off of Farm View Drive as you enter the complex is a great place to stop along your ride.
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Brandy Pond is big enough that it also goes by the name Bay of Naples Lake. It is one of a few lakes in this area and is connected to Long Lake by the Chute River and to Sebago Lake by the Songo River.
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Sebago Lake is the second-largest reservoir within the state of Maine, encompassing roughly 45 square miles. This is an official overlook spot and parking area on the southern end of the lake. The more popular state park is on the northern side of the reservoir.
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Brandy Pond is big enough that it also goes by the name Bay of Naples Lake. It is one of a few lakes in this area and is connected to Long Lake by the Chute River and to Sebago Lake by the Songo River.
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Sebago Lake is the second-largest reservoir within the state of Maine, encompassing roughly 45 square miles. This is an official overlook spot and parking area on the southern end of the lake. The more popular state park is on the northern side of the reservoir.
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Sebago Lake is the second-largest reservoir within the state of Maine, encompassing roughly 45 square miles. This is an official overlook spot and parking area on the southern end of the lake. The more popular state park is on the northern side of the reservoir.
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Brandy Pond is big enough that it also goes by the name Bay of Naples Lake. It is one of a few lakes in this area and is connected to Long Lake by the Chute River and to Sebago Lake by the Songo River.
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Cumberland County offers a diverse range of landscapes for road cyclists. In Maine, you'll find extensive coastlines with ocean vistas, iconic lighthouses like Portland Head Light, and routes along bays and through forested preserves. In Pennsylvania, routes often traverse quiet back roads, picturesque farmland, wooded areas, and offer views of mountains and creeks, such as the Yellow Breeches Creek.
Yes, Cumberland County has numerous easy routes suitable for families and beginners. For instance, the Pine Grove Preserve & Presumpscot Falls loop from Portland is an easy 19.3-mile (31.0 km) path. The South Portland Greenbelt Walkway is another easy option, and the Cumberland Valley Rail Trail in Pennsylvania is a crushed limestone path suitable for most bicycles, winding through scenic farmland.
For longer rides, consider routes like the East Coast Greenway: Portland to Brunswick Loop, which spans over 68 miles (109 km). Another substantial option is the Simpson's Point from Portland route, covering nearly 62 miles (99 km).
The terrain in Cumberland County generally includes rolling hills. Many routes offer moderate elevation changes, such as the Sebago Lake loop with over 430 meters of ascent. Some areas, particularly in Pennsylvania's mountainous regions like Kings Gap, can offer more gradual climbs with rewarding valley views.
Many routes offer scenic viewpoints and pass by significant attractions. In Maine, you can cycle past the iconic Portland Head Light at Fort Williams Park, enjoy views of Casco Bay, or explore the Back Cove Trail. In Pennsylvania, routes may lead to the historic Pine Grove Iron Furnace, the Appalachian Trail Museum, or offer expansive views from Kings Gap Environmental Education Center.
Yes, many road cycling routes in Cumberland County are designed as loops. Popular examples include the Portland Head Light loop via Robinson Preserve & Scarborough Beaches Bike Route, the Sebago Lake loop, and the East Coast Greenway: Portland-Yarmouth Loop. Pennsylvania also features several loop rides, such as the Carlisle to Boiling Springs Loop.
The road cycling routes in Cumberland County are highly rated by the komoot community, with an average score of 4.5 stars from over 90 reviews. Cyclists often praise the varied terrain, from coastal paths to lake views and forested routes, and appreciate the options available for different ability levels.
Yes, many routes pass through or near charming towns and local points of interest where you can find amenities. For instance, routes in Cumberland County, Maine, often connect to Portland, Yarmouth, and Brunswick, which offer various services. In Pennsylvania, routes frequently include stops in quaint towns with farmers' markets and other local establishments. For specific information on amenities along routes in Cumberland Valley, you can check resources like Visit Cumberland Valley.
Absolutely. Cumberland County, Maine, is renowned for its coastal cycling. The Portland Head Light loop via Robinson Preserve & Scarborough Beaches Bike Route and the 8.3-mile Back Cove and Eastern Promenade Trail Loop are excellent choices for ocean vistas and views of the Portland skyline and Casco Bay.
While specific seasonal advice can vary, the spring, summer, and fall months generally offer the most pleasant conditions for road cycling in Cumberland County. During these seasons, the weather is typically mild, and the natural scenery, from coastal blooms to autumn foliage, is at its most vibrant. Always check local weather forecasts before heading out.
Yes, several routes in Cumberland County incorporate beautiful waterways. The Sebago Lake loop offers stunning lake views through rural areas. In Pennsylvania, routes often pass along the Yellow Breeches Creek, known for fly fishing, and the Conodoguinet Creek, with its diverse plant species.
There are over 330 road cycling routes available in Cumberland County, catering to various skill levels. This includes 122 easy routes, 200 moderate routes, and 9 difficult routes, ensuring options for every cyclist.


Check out more Road cycling routes throughout Cumberland County below and find the perfect route in your destination.
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