4.7
(12)
458
riders
51
rides
Road cycling routes around Littlejohn Island offer diverse terrain characterized by coastal views of Casco Bay and accessible road networks. The island and its surroundings feature a blend of dense woodlands, open meadows, and rocky shores. While some areas are relatively flat, routes can include varying elevation gains, providing options for different fitness levels.
Last updated: July 13, 2026
70
riders
56.8km
02:31
380m
380m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
17
riders
38.4km
01:46
320m
320m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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16
riders
43.5km
02:02
330m
330m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
16
riders
36.6km
01:42
320m
320m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(6)
10
riders
65.7km
02:52
500m
500m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Littlejohn Island
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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Lower Mast Landing Road is a pretty, forested road just outside of downtown Freeport, Maine. You ride past Quarry Woods, a popular local hiking spot that has a former granite quarry, an old apple orchard, seasonal ponds, and hiking trails on this quiet road.
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Kelsey Hill is a small hill just outside of downtown Freeport right at the bend of Bow Street. This short climb is a nice way to warm up the legs in this relatively flat, seaside town.
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Downtown Freeport, Maine, is a great place to spend an afternoon. This charming little town has a great shopping scene, and diverse dining options. At its heart lies the iconic L.L. Bean flagship store, open round the clock and offering an extensive array of outdoor gear and apparel. Be sure to grab a photo with the iconic "Bean Boot!" After shopping at L.L. Bean, there are cozy cafes to upscale restaurants specializing in fresh seafood.
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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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First Falls is a set of rapids and small cascades on the Royal River. You get a great view from here on the Main Street Bridge, or you can hop off the bike at Grist Mill Park and get right next to the edge of the water.
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You get really nice views of the Royal River Reservoir as you ride over the water on Elm Street. You can see the Royal River Train Bridge as well as Gooch's Island from here.
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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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There are over 50 road cycling routes around Littlejohn Island. These routes cater to various fitness levels, with 19 classified as easy and 31 as moderate. There are no difficult routes listed, making the area accessible for a wide range of cyclists.
Road cycling around Littlejohn Island offers diverse terrain, characterized by coastal views of Casco Bay, dense woodlands, open meadows, and rocky shores. While many areas are relatively flat, some routes include varying elevation gains, providing a good mix of challenges and scenic stretches. You'll find accessible road networks connecting the island to Cousins Island and the mainland.
Absolutely! The region is rich in natural beauty. You can enjoy breathtaking ocean-front views of Casco Bay, explore secluded rocky beaches, and ride through forests of spruce and birch. Notable natural features include the Harraseeket Trail and the diverse ecosystems of the Littlejohn Island Preserve. Routes like Nice view of an inlet of Maquoit Bay – Spectacular mud flats loop from Rest Area Welcome Center offer scenic views of Maquoit Bay and its mud flats.
The area is highly rated by the komoot community, with an average score of 4.6 stars from 6 reviews. Cyclists often praise the diverse terrain, from coastal paths to dense woodlands, and the scenic inlets. The variety of routes, catering to different ability levels, is also a significant draw, allowing many to explore Littlejohn Island's varied landscape.
Yes, many of the road cycling routes around Littlejohn Island are designed as loops, allowing you to start and end at the same point. For example, the Portland Harbor – Views of Casco Bay loop from Littlejohn Island offers expansive views of Casco Bay, and the Royal River Park loop from Arnold Family Forest provides an easy option.
The region's natural beauty, with its woodlands and coastal views, makes it appealing across seasons. While specific recommendations depend on personal preference, spring and fall often offer pleasant temperatures and vibrant scenery. Summer provides warmer weather for coastal rides, and the island's peaceful nature is enjoyable throughout the milder months.
Yes, Littlejohn Island and its surroundings offer several easy road cycling routes suitable for families. The relatively flat terrain in many areas, combined with accessible routes, makes it suitable for various fitness levels. You can find 19 easy routes in the area, providing gentle rides through scenic landscapes.
While vehicular parking can be limited in some areas, particularly near the Littlejohn Island Preserve, cycling is encouraged as an ideal alternative for accessing the preserve. Bike racks are available at the trailhead. For other routes, parking availability may vary, often found in nearby towns or designated areas along the routes.
Yes, the routes often pass by or near interesting places. You can cycle past the Sandy Point Beach, explore the charming Downtown Freeport, or discover the Woods and Waters of Wolfe's Neck. The landscape also holds historical significance, with old stone walls and remnants of farmsteads adding intrigue to your ride.
Yes, for those seeking longer rides, there are several moderate routes available. For instance, the Lower Mast Landing Road – Nice View loop from River's Edge covers over 62 kilometers and offers a substantial challenge with significant elevation gain. Another option is the Portland Harbor – Views of Casco Bay loop from Littlejohn Island, which is over 56 kilometers long.
The average duration for road cycling routes around Littlejohn Island varies significantly depending on the route's length and your pace. For example, the Portland Harbor – Views of Casco Bay loop from Littlejohn Island typically takes about 2 hours and 30 minutes, while the Lower Mast Landing Road – Sandy Point Beach loop from Cousins Island can be completed in approximately 1 hour and 59 minutes.


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