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Routes
Road cycling routes
United States
Maine

Cumberland County

The best road cycling routes in Cumberland County

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.

Best road cycling routes in Cumberland County

  • The most popular…

Last updated: April 24, 2026

4.5

(2)

158

riders

#1.

Portland Head Light loop via Robinson Preserve & Scarborough Beaches Bike Route

49.7km

02:42

230m

230m

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Moderate

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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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.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

19

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

4.0

(1)

17

riders

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

16

riders

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

6

riders

36.0km

01:48

440m

440m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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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

Other adventures in Cumberland County

On the trail of the Pilgrim Fathers – road trip along the Atlantic coast

Hiking Collection by

VisitTheUSA

Tips from the Community

Marius
June 1, 2025, Portland Head Light

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.

Translated by Google

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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.

1

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Matthew
December 10, 2023, Brandy Pond

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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Matthew
December 10, 2023, View of Sebago Lake

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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0

Matthew
December 9, 2023, Brandy Pond

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.

0

0

Matthew
December 9, 2023, View of Sebago Lake

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.

0

0

Matthew
December 9, 2023, View of Sebago Lake

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.

0

0

Matthew
December 9, 2023, Brandy Pond

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.

0

0

Frequently Asked Questions

What types of landscapes can I expect to see while road cycling in Cumberland County?

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.

Are there any easy or family-friendly road cycling routes in Cumberland County?

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.

What are some of the longer road cycling routes available in Cumberland County?

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).

What kind of elevation changes can I expect on road cycling routes in Cumberland County?

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.

What are some notable landmarks or attractions I can see along the road cycling routes?

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.

Are there any circular road cycling routes in Cumberland County?

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.

What do other road cyclists say about the routes in Cumberland County?

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.

Can I find amenities like cafes or accommodation near the road cycling routes?

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.

Are there any specific routes that offer coastal views?

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.

What is the best time of year to go road cycling in Cumberland County?

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.

Are there any routes that feature lakes or rivers?

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.

How many road cycling routes are there in Cumberland County?

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.

Most popular routes in Cumberland County

Hiking in Cumberland County

Most popular attractions in Cumberland County

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Didn’t find what you were looking for?

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

PortlandBrunswickCousins IslandFalmouthGorhamBradbury Mountain State ParkWestbrookOak HillSouth PortlandBridgtonDunstanFreeportNaplesSouth WindhamSteep FallsLittlejohn IslandCumberland CenterMorgan Meadow WmaFalmouth ForesideLittle FallsGrayNorth WindhamKettle Cove State ParkYarmouthStandishCascoScarborough Beach State ParkCrescent Beach State ParkSebago Lake

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Things to Do around Cumberland Center

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