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United States
Maine
Cumberland County

Westbrook

The best cycling routes around Westbrook

By Fede from komoot

·

Updated June 2, 2026

If you've ever tried to plan touring cycling around Westbrook, you know how many routes pop up, making it tough to tell which ones are genuinely worth your time and effort. It's easy to get overwhelmed trying to find the real highlights among all the options. That's where komoot comes in. Our community has ridden, reviewed, and mapped the best touring cycling routes here, saving you the guesswork and pointing you straight to the rides that are truly worth your legs.

Touring cycling around Westbrook feels like a true Maine experience, defined by the scenic Presumpscot River and its surrounding wooded areas. You'll find a great mix of flat, easy river trails and more varied paths, with some routes even extending towards the coast. The terrain is generally accessible, with gentle climbs and rolling hills that offer a good range from relaxed spins to more moderate challenges. The region really shines with its riverine paths, wooded trails, and connections to coastal routes.

If you only do one ride, we'd start with the popular Sebago to the Sea Trail Loop. At 29.3 miles (47.2 km) with about 990 feet (302 m) of elevation gain, it’s a moderate ride that delivers diverse terrain and fantastic river views. For something a bit easier, the Mountain Division and Presumpscot River Loop is a local favorite, offering a flat 9.6 miles (15.5 km) along the river. With over 900 touring cyclists having explored Westbrook's varied terrain with komoot, you can trust these routes to deliver.

If you only do 3 of these routes

  1. 1

    Sebago to the Sea Trail Loop
  2. 2

    Mountain Division and Presumpscot River Loop
  3. 3

    Views of Casco Bay – East End Beach loop from Mayor Baxter Woods

Compare these routes at a glance

Trail

Distance

Elevation

Difficulty

Sebago to the Sea Trail Loop

47.2 km

300 m

Moderate

Mountain Division and Presumpscot River Loop

15.5 km

130 m

Easy

Views of Casco Bay – East End Beach loop from Mayor Baxter Woods

15.5 km

60 m

Easy

South Portland Greenbelt – Eastern Trail loop from Portland

43.1 km

140 m

Moderate

Back Cove Trail – Back Cove Crane Sculpture loop from Portland

52.9 km

330 m

Moderate

Scarborough Marsh – Portland Harbor loop from Portland

88.1 km

370 m

Hard

Eastern Promenade Trail – Portland Head Light at Fort Williams Park loop from Portland

50.8 km

290 m

Moderate

Red's Dairy Freeze – Bug Light Park loop from Sandy Hill

18.1 km

70 m

Easy

Eastern Promenade Trail – Portland Harbor loop from Riverside St + Hannaford

44.4 km

180 m

Moderate

Pine Grove Preserve – Baxter Boulevard Bike Route loop from Riverside St + Hannaford

23.2 km

170 m

Moderate

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1.

Sebago to the Sea Trail Loop

47.2km

03:10

300m

300m

The Sebago to the Sea Trail Loop offers a dynamic touring bicycle experience, tracing a path from the tranquil Sebago Lake all the way to the salty air of Casco Bay. You'll ride through lush forests and charming rural communities, with continuous scenic views along the Presumpscot River. While some sections are smoothly paved, be ready for stretches of loose gravel and undeveloped railbeds, making a mountain or gravel bike ideal for this moderate 29.3-mile (47.2 km) route.

Planning your ride requires a bit of foresight, as the trail is still under development in some areas, which might mean detours or sections designated for foot traffic only. Access points like Shaw Park in Gorham and Johnson Field in Standish provide convenient starting locations. Be sure to check if a permit is needed for any sections, especially those on Portland Water District land, to ensure a smooth journey.

This trail uniquely connects two significant bodies of water, offering a journey from a vast inland lake to the Atlantic Ocean. It incorporates parts of the historic Mountain Division Trail, adding a layer of regional heritage to your ride. With 990 feet (302 metres) of elevation gain over approximately 3 hours and 9 minutes, it's a fantastic option for cyclists looking for a diverse and engaging route that showcases Maine's natural beauty and evolving recreational infrastructure.

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2.

Mountain Division and Presumpscot River Loop

15.5km

00:57

130m

130m

The Mountain Division and Presumpscot River Loop offers a delightful blend of smooth rail trail and natural riverside paths, making it a unique touring cycling experience. You'll pedal through open woods and past farm fields, enjoying exceptional views of the Presumpscot River, with the charming Babb's Bridge as a notable landmark. The varied terrain keeps things interesting, moving from paved sections to more rugged, unpaved riverside trails.

This easy 9.6-mile (15.5 km) loop, with a modest 428 feet (130 metres) of elevation gain, can typically be completed in under an hour, around 57 minutes. While the Mountain Division Trail sections are generally flat and accessible, the Presumpscot River portions introduce more challenging, rooty, and sometimes steeper segments, so be prepared for a mix of surfaces. It's a great option for cyclists looking for a quick, diverse ride.

Historically significant, the Mountain Division Trail follows an old railroad bed, and the nearby Gambo Preserve holds the remains of Maine's first gunpowder mill. This route is also part of the larger Sebago to the Sea Trail, connecting communities and offering a glimpse into the region's natural and industrial past. Keep an eye out for waterfowl and, in spring, alewives in the river.

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3.

Views of Casco Bay – East End Beach loop from Mayor Baxter Woods

15.5km

00:55

60m

70m

This easy 9.6-mile (15.5 km) touring cycling route offers a unique blend of Portland's natural beauty, taking you from the shaded, forested paths of Mayor Baxter Woods to the expansive coastal views of the Eastern Promenade Trail. You'll pedal through tranquil red pine stands and past a small pond before emerging to continuous vistas of Casco Bay and its islands, with East End Beach as a scenic highlight. The 211 feet (64 metres) of elevation gain are spread out, making for a relaxed ride that can be completed in about 55 minutes.

To tackle this cycling route from Mayor Baxter Woods to the Eastern Promenade Trail, be prepared for some urban navigation. The loop requires connecting different trail systems via city streets, linking the forested preserve to the Back Cove Trail and then the paved waterfront path. This makes for a diverse experience, but planning your transitions is key to a smooth journey. Consider starting in the morning to enjoy the best light over Casco Bay.

This route is a fantastic way to experience Portland, Maine, offering a family friendly cycling trail that showcases both its urban green spaces and its iconic coastline. The Eastern Promenade Trail section is part of the larger East Coast Greenway, providing opportunities for longer rides, while Mayor Baxter Woods offers a peaceful urban oasis. It's a great option for those looking for easy bike rides Portland Maine that combine varied scenery.

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6.

Scarborough Marsh – Portland Harbor loop from Portland

88.1km

05:27

370m

370m

The Scarborough Marsh – Portland Harbor loop offers a truly diverse touring cycling experience, guiding you through stunning coastal landscapes and the unique ecosystem of Maine's largest salt marsh. You'll traverse extensive marshlands, wetlands, and woods, with expansive views of the Atlantic Ocean and Portland Harbor, particularly from Bug Light Park. Expect a mix of paved surfaces, packed dirt, and crushed gravel, providing a varied terrain under your wheels.

This difficult 54.8-mile (88.1 km) route, with 1211 feet (369 metres) of elevation gain, is a serious undertaking that typically takes around 5 hours and 27 minutes. Be prepared for a challenging ride, including a 4-mile on-road stretch between Scarborough and South Portland that can be busy with traffic and has narrow sections. This loop is best suited for confident touring cyclists looking for a full day's adventure.

Much of the route utilizes the Eastern Trail, a multi-use greenway that forms part of the larger East Coast Greenway, offering mostly off-road cycling through scenic areas. The Scarborough Marsh itself is a critical habitat for wildlife and holds historical significance, including a canal dug during the American Revolutionary War. This trail provides a fantastic opportunity for wildlife viewing, especially birdwatching, as you cycle through this unique coastal environment.

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7.

Eastern Promenade Trail – Portland Head Light at Fort Williams Park loop from Portland

50.8km

03:04

290m

290m

This popular cycling route from the Eastern Promenade Trail to Portland Head Light at Fort Williams Park offers a fantastic blend of urban waterfront and rugged coastal beauty. You'll cruise along the paved Eastern Prom with continuous views of Casco Bay, then transition to South Portland and Fort Williams Park, where the iconic Portland Head Light stands proudly on a rocky promontory. It's a moderate touring cycling route covering 31.7 miles (51.0 km) with about 950 feet (289 metres) of elevation gain, typically taking around 3 hours and 4 minutes to complete.

Planning your visit is straightforward, as both the Eastern Promenade and Fort Williams Park are highly accessible. The Eastern Prom is a smooth, paved multi-use path, while the journey to Fort Williams Park involves a mix of roads, dedicated bike lanes, and some crushed stone paths within the park itself. This makes the route suitable for a variety of skill levels, and e-bikes can make any climbs feel effortless. Consider an early start to enjoy the scenic viewpoints and avoid the busiest times, especially around the lighthouse.

What makes this route truly special is its connection of two of Portland's most famous attractions, offering stunning coastal views throughout. The Eastern Promenade itself was designed by the Olmsted Brothers, and Fort Williams Park is steeped in military history, with remnants of its past alongside the picturesque lighthouse. This cycling route is also part of the larger East Coast Greenway, providing a sense of connection to a broader network of trails.

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8.

Red's Dairy Freeze – Bug Light Park loop from Sandy Hill

18.1km

01:04

70m

70m

This easy touring cycling route offers a delightful spin along the South Portland Greenbelt, providing picturesque views of Portland Harbor and the city skyline. You'll pedal 11.2 miles (18.1 km) with just 226 feet (69 metres) of elevation gain, making it a perfect choice for a relaxed outing that takes about 1 hour and 4 minutes. The journey culminates at the charming Portland Breakwater Lighthouse in Bug Light Park, where you can watch boats pass by.

Planning your ride is straightforward, as the Greenbelt Walkway is largely paved and very accessible, ideal for families or those new to cycling. While specific parking for a "Sandy Hill" start isn't provided, Bug Light Park offers convenient parking. This route is suitable for most touring bikes and can be enjoyed during good weather conditions, though coastal breezes are common.

Beyond the scenic waterfront, this loop connects you to the northern end of the Eastern Trail, a much larger multi-use greenway. A key highlight is the chance to stop at Red's Dairy Freeze, a beloved local institution known for its soft-serve ice cream, making it a popular and iconic refreshment stop for cyclists in the area.

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9.

Eastern Promenade Trail – Portland Harbor loop from Riverside St + Hannaford

44.4km

02:41

180m

180m

This Portland Harbor loop cycling route offers an incredibly scenic ride, tracing the city's beautiful waterfront. You'll cruise along paved paths, taking in continuous views of Casco Bay, its islands, and the bustling harbor, often with cruise ships and historic trains in sight. The route transitions from the vibrant Eastern Promenade, passing through its historic park, to the tranquil Back Cove, providing a diverse and engaging experience for touring cyclists.

Planning your ride is straightforward, with a convenient starting point often found near the Hannaford Supermarket on Forest Avenue, which links directly to the Back Cove Trail. This moderate 27.6-mile (44.4 km) loop, with a gentle 587 feet (179 metres) of elevation gain, takes approximately 2 hours and 40 minutes to complete. Parking is generally available near the Eastern Promenade park or the Hannaford, but remember to share the path respectfully with other users, as it's a popular spot.

What makes this route truly special is its blend of natural beauty and urban charm, forming a vital part of the East Coast Greenway. Beyond the stunning views, you'll encounter historic buildings and public art, with opportunities to stop at East End Beach or explore Portland's Old Port. It's an ideal choice for anyone seeking a rewarding, accessible touring cycling adventure around Portland, Maine.

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Tips from the Community

Helengfox
September 21, 2024, Babb's Bridge

I love this bridge. But, a dump truck tried to cross it and collapsed the floor. Not sure the repair time frame. 9/21/24

0

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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/

Translated by Google

2

0

Gilman Road takes you past Fels-Grove Farm Preserve. The natural woodlands make this a shaded stretch of road, much appreciated in the warmer summer months.

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Royal River Park is a small, scenic park next to the Royal River and just southeast of the Yarmouth History Center. This is a nice place to pause on a long ride and take a break from being in the saddle.

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Scott
February 14, 2024, Mayor Baxter Woods

A diverse ecosystem supporting a variety of wildlife, including birds, squirrels, and even foxes. It's a designated municipal forest and bird sanctuary, recognized for its ecological value.

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Matthew
February 14, 2024, East End Beach

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

Gilman Road takes you past Fels-Grove Farm Preserve. The natural woodlands make this a shaded stretch of road, much appreciated in the warmer summer months.

0

0

Casco Bay is an inlet of the Gulf of Maine. The bay gets its name from its shape. The Portuguese explorers called the area "Bahia de Cascos", which means Bay of Helmets.

0

0

Frequently Asked Questions

How many touring cycling routes are available around Westbrook?

There are nearly 100 touring cycling routes around Westbrook, offering a wide variety of options for different skill levels. You'll find 65 easy routes, 29 moderate routes, and 5 difficult routes to explore.

What types of terrain can I expect on Westbrook's touring cycling routes?

Westbrook's touring cycling routes are primarily shaped by the Presumpscot River, offering a mix of flat river trails and varied paths. You'll encounter wooded areas and connections to coastal routes. Elevations are generally low, with some gentle climbs and hills, making the terrain accessible for various cycling abilities.

Are there any family-friendly touring cycling routes in Westbrook?

Yes, many routes are suitable for families. The Mountain Division and Presumpscot River Loop is an easy 9.6-mile (15.5 km) path that combines the flat Mountain Division Trail with scenic paths along the Presumpscot River, perfect for a family outing.

What are some notable natural features or landmarks I can see along the routes?

The Presumpscot River is a central feature, with the Westbrook River Walk tracing its path and showcasing historic mill buildings and a waterfall. You can also find highlights like Portland Harbor, the Eastern Promenade Trail, and East End Beach, which offer scenic views and points of interest.

Are there any circular touring cycling routes in the Westbrook area?

Yes, several routes are loops. For instance, the Eastern Promenade Trail – Back Cove Trail loop from Portland is an 11.1-mile (17.8 km) trail that takes you through urban waterfronts and green spaces, offering a convenient circular ride.

What is the best time of year to go touring cycling in Westbrook?

The region offers pleasant cycling conditions through spring, summer, and fall. Spring brings the alewife migration at Mill Brook Preserve, while summer is ideal for enjoying the river and coastal views. Fall offers beautiful foliage. Always check local weather conditions before heading out.

Where can I find parking for touring cycling routes in Westbrook?

Parking is generally available near trailheads and public parks in Westbrook. For routes like the Mountain Division Trail or those along the Presumpscot River, look for designated parking areas in Westbrook's parks and open spaces. For more specific information, you can check the Westbrook Parks, Recreation & Open Spaces website.

What do other touring cyclists say about the routes in Westbrook?

The touring cycling routes in Westbrook are highly rated by the komoot community, with an average score of 4.4 stars from over 60 reviews. Cyclists often praise the varied terrain, scenic river views, and the accessibility of routes for different skill levels.

Are there any longer touring cycling routes available from Westbrook?

Yes, for a longer adventure, consider the Sebago to the Sea Trail Loop. This route is 29.3 miles (47.2 km) and connects Sebago Lake to Casco Bay, offering diverse terrain and extensive river views for a more extended ride.

Can I find routes that offer coastal views or connect to the coast?

Absolutely. While Westbrook itself is river-centric, some routes extend towards coastal areas. The Sebago to the Sea Trail Loop connects to Casco Bay, and routes like the Casco Bay Bridge – Crescent Beach State Park loop from Portland offer beautiful coastal scenery.

Are there any easy touring cycling routes for beginners?

Yes, Westbrook offers several easy routes perfect for beginners. The Mountain Division and Presumpscot River Loop is an excellent choice, combining flat trails with scenic river paths over 9.6 miles (15.5 km).

What kind of natural attractions can I expect to see along the Presumpscot River?

The Presumpscot River is a highlight, featuring two prominent falls, Saccarappa Falls and Congin Falls. The Westbrook River Walk provides excellent views of the river and its natural beauty, including the possibility of seeing the famous ice disk if you visit in winter.

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