The best road cycling routes around Winslow
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riders
13
rides
Road cycling routes around Winslow offer a variety of terrain suitable for different skill levels. The region provides a mix of quiet country roads and undulating landscapes. While specific geographical features are not detailed in the provided data, the area is generally characterized by its rural setting. Road cyclists can expect to find routes that traverse open countryside, providing opportunities for varied rides.
Best road cycling routes around Winslow
- The most popular road cycling route is Messalonskee Lake loop from…
Last updated: May 21, 2026
2
riders
60.6km
02:45
480m
480m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
1
riders
66.5km
03:08
550m
550m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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119km
05:08
820m
820m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5
riders
54.2km
02:49
410m
410m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
17.2km
00:59
190m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Winslow
Tips from the Community
Colby College sits on 714 acres at the top of Mayflower Hill in Waterville. It's known for its New-Georgian architecture, and has an enrollment of just 2,000 students.
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Picturesque pond on the campus of Colby College. There are a number of benches around the pond to sit and enjoy the scenery.
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Mill Island Park is a great little park in the middle of the Kennebec River. There are picnic area, walking paths, a playground, and more.
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This public footbridge was built in the early 1900s with a toll of 1 cent. After less than a year the original bridge was destroyed in a flood and subsequently rebuilt. The toll was also raised to 2 cents, which is where the common name comes from though the official name is still Ticonic Footbridge. These days there is no toll to cross the bridge, which was added to the National Register of Historic Places in 1973.
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Augusta, Maine's State Capital, sits along the banks of the Kennebec River. It's the 3rd smallest U.S. State Captial by population & offers a unique mixture of historic buildings, great restaurants, & ample opportunities to explore the river and other outdoor destinations.
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The 170 mile long Kennebec River is an important recreational and commercial resource for the region. Recently the runs of Atlantic Salmon have started to recover after the removal of the Edwards Dam.
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China Lake is a popular destination for water lovers of all stripes, including those that prefer it frozen. The lake and nearby town of the same name have no connection to the seemingly eponymous country of China. Instead the name derives from an old hymn by Timothy Swan that was popular around the time the town was founded.
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Messalonskee Lake is one of 5 lakes within the Belgrade Lakes Region. It is a naturally occurring lake, though it has been artificially enlarged with a dam. It's a popular destination for fishing, boating, swimming, and bird & other wildlife spotting.
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Frequently Asked Questions
How many road cycling routes are available around Winslow?
There are 13 road cycling routes around Winslow listed on komoot, offering a variety of experiences for different skill levels.
Are there easy road cycling routes suitable for beginners in Winslow?
Yes, Winslow offers 5 easy road cycling routes. A good option for beginners is the Colby College – Johnson Pond loop from Colby College, which is 10.7 miles (17.2 km) long with a modest elevation gain of 607 feet (185 meters).
What are some moderate road cycling routes in the Winslow area?
For those seeking a moderate challenge, Winslow has 7 routes. Popular choices include the Messalonskee Lake loop from Waterville, Maine, a 37.7-mile (60.6 km) ride with 1,579 feet (481 meters) of ascent, and the China Lake loop from Waterville, Maine, covering 41.3 miles (66.5 km) with 1,793 feet (546 meters) of elevation gain.
Are there any challenging road cycling routes for experienced riders near Winslow?
Yes, there is one difficult road cycling route for experienced riders. The Kennebec River loop via the East Coast Greenway is a demanding 74.0-mile (119.0 km) trail with a significant elevation gain of 2,696 feet (821 meters), typically taking over 5 hours to complete.
What kind of terrain can I expect on road cycling routes around Winslow?
Road cycling routes around Winslow feature a mix of quiet country roads and undulating landscapes. The area is characterized by its rural setting, offering rides that traverse open countryside with varied elevation profiles.
Are there any circular road cycling routes in Winslow?
Many of the routes around Winslow are designed as loops, offering circular rides. Examples include the Messalonskee Lake loop from Waterville, Maine and the China Lake loop from Waterville, Maine, both popular circular options.
What are some scenic viewpoints or attractions along road cycling routes near Winslow?
While cycling, you can enjoy views of natural features like China Lake. Other points of interest include the historic Ticonic Footbridge (Two Cent Bridge) and Mill Island Park. The routes often pass through the charming settlement of Waterville, Maine.
Are there any routes that pass by educational institutions or notable landmarks?
Yes, some routes offer views of local institutions. For instance, the Colby College – Johnson Pond loop from Colby College starts and ends near Colby College, a prominent local landmark.
What do other road cyclists say about the routes around Winslow?
Over 26 road cyclists have explored Winslow's varied terrain using komoot. They often appreciate the region's quiet country roads and the diverse range of routes available, catering to different ability levels.
Which route is a good option for a longer, moderate ride that includes a park?
The Waterville, Maine – Mill Island Park loop from Fairfield is a moderate 33.7-mile (54.2 km) route that includes a visit to Mill Island Park, offering a pleasant stop during your ride.
What is the best time of year for road cycling in Winslow?
The rural setting and varied landscapes of Winslow make it enjoyable for road cycling across multiple seasons. Spring and autumn typically offer pleasant temperatures and scenic views, while summer provides longer daylight hours. Winter conditions may vary, so checking local weather is always recommended.
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