4.4
(13)
1,696
runners
113
runs
Jogging around Westbrook offers diverse routes along scenic riverfronts and through natural landscapes. The region features a mix of paved surfaces, gravel paths, and natural trails, providing varied terrain for runners. Elevation changes can be found on some routes, while others offer flatter options. Westbrook's extensive trail network connects urban areas with preserves and green spaces.
Last updated: June 25, 2026
33
runners
21.1km
02:12
90m
90m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
11
runners
4.19km
00:30
20m
20m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(3)
154
runners
17.6km
01:50
100m
100m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
36
runners
25.7km
02:42
180m
180m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
29
runners
47.4km
04:56
300m
300m
Hard run. Very good fitness required. Mostly accessible paths. Some sure footedness required.
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A place with a nice overlook. Good to have a short stop.
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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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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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The Back Cove Trail is one of the oldest and most popular trails in Portland. As the name suggests, it encircles Back Cove.
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The woods boast a network of trails that are perfect for walking, hiking, running, and biking. There's even a wheelchair-accessible loop, making it enjoyable for everyone.
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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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The Cherry Hills Trail System is mostly flat and built with gravel. It was completed only a few years ago. You'll hike through woods and along some large fields. Along the way, benches cut from fallen trees invite you to take a break.
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Westbrook offers a wide variety of running experiences, with over 100 routes documented on komoot. These range from easy strolls to more challenging runs, ensuring options for all fitness levels.
The running routes around Westbrook feature a diverse mix of terrains. You'll find paved surfaces, gravel paths, and natural trails winding through woods and fields. Some trails, like sections of the East Coast Greenway, offer significant elevation changes, while others, such as the Burleigh Lovett Trail, provide easier, flatter options.
Absolutely! The River Walk in downtown Westbrook is a central feature for runners, offering picturesque views along the Presumpscot River. The River Walk Loop extends this experience, crossing the river and leading into the Frenchtown neighborhood, providing a mix of urban and natural scenery.
Yes, the Sebago to the Sea Trail is a significant route that forms part of a larger system connecting Sebago Lake to Casco Bay. This extensive trail winds through both downtown Westbrook and natural areas along the river, providing diverse scenery for longer runs.
The running routes in Westbrook are highly rated by the komoot community, with an average score of 4.3 stars from over 10 reviews. Runners often praise the diverse terrain, the beautiful riverfront paths, and the variety of options available for different ability levels.
Yes, Westbrook Recreational Park offers a tranquil environment with well-maintained, wheelchair-friendly paths that are ideal for walking and running with a stroller. For easier, flatter options, the Burleigh Lovett Trail is also a great choice for families.
Many of Westbrook's trails are dog-friendly, allowing you to enjoy a run with your canine companion. Trails like the River Walk and those in the Mill Brook Preserve are popular choices, but always remember to keep your dog on a leash and clean up after them.
While jogging, you might encounter various points of interest. The River Walk itself offers views of the Presumpscot River. For broader attractions nearby, consider exploring Portland Harbor or the Eastern Promenade Trail, which are accessible from some of the longer routes connecting Westbrook to Portland.
Parking is generally available at various access points for Westbrook's trails. For instance, you can often find parking near the River Walk behind restaurants on Bridge Street or near Fraser Softball Field. For specific trailheads, it's advisable to check local signage or the Westbrook city website for detailed parking information: westbrookmaine.gov/482/Trails.
Yes, Westbrook offers several circular running routes. A popular option is the Canco Woods – Pine Grove Preserve loop from Cheverus High School, which provides a substantial 15.9-mile (25.6 km) circuit through natural areas. The River Walk Loop also offers a shorter, scenic circular experience.
Westbrook offers great running opportunities throughout the year. Spring and fall provide pleasant temperatures and beautiful foliage. Summer is excellent for early morning or evening runs to avoid the heat, while winter running is possible on cleared paths, though some natural trails may be snowy or icy. Always check local conditions before heading out.
Yes, Westbrook's trail system is well-connected. The Sebago to the Sea Trail links Westbrook to Sebago Lake and Casco Bay. Additionally, the Stroudwater Trail extends the system, connecting to the Fore River Sanctuary in Portland, offering opportunities for longer runs and exploration into broader natural areas.


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