4.7
(66)
1,398
riders
162
rides
Road cycling routes around Old Hill are characterized by undulating terrain, offering a mix of challenging climbs and rewarding descents. The region features hilly landscapes with varied topography, providing significant elevation changes suitable for road cyclists. These routes often traverse areas with forests and woodlands, contributing to varied scenery.
Last updated: June 30, 2026
43
riders
41.1km
01:49
270m
270m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(26)
33
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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19
riders
59.6km
02:41
510m
510m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
41.7km
01:57
400m
400m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5
riders
54.4km
02:43
450m
440m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Old Hill
Great Training Course. Good climbs, nice long flat parts to do sprints and pace changes. I did 3 loops. very good course.
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Camp Tepee is a popular camp for all ages run by the Lakewood-Trumbull YMCA. As you zip by on your bike, enjoy the pond and forest setting just off the side of the road.
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Streets Pond is a long, thin, and stretches under the road as you ride by. There are wooden fences that make it difficult to get a good view from the road, but if you pull up on the sidewalk you can look down the length of the forested pond.
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The Saugatuck Reservoir, an 827-acre manmade lake in Fairfield County, offers an angler's paradise just off the I-95 corridor. From Newtown Turnpike, you can catch beautiful views through the woods surrounding the reservoir, often with reflections of the sky in the still water.
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Pear Tree Point Cove is a sheltered inlet off Long Island Sound, providing a calm environment for various marine life. The diverse birdlife in and around the cove attracts birdwatchers, offering opportunities to observe various species throughout the year. The cove offers stunning water views and is surrounded by lush greenery, making it a picturesque location for relaxation.
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The Aspetuck Reservoir, nestled along the Aspetuck River offers breathtaking views for cyclists throughout the year. Its scenic beauty is especially captivating during the fall season, providing cyclists with a picturesque backdrop for their rides.
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You get a great view of the Aspetuck River as you bike across this small bridge. The river is only 17 miles, and there are only a few spots where you get a view as good as this one.
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You get a great view of the Aspetuck River as you bike across this small bridge. The river is only 17 miles, and there are only a few spots where you get a view as good as this one.
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Road cycling routes in this area are characterized by undulating terrain, offering a mix of challenging climbs and rewarding descents. You'll find varied topography, from gentle inclines to demanding ascents, often passing through scenic forests and woodlands. The routes are designed to provide significant elevation changes suitable for road cyclists.
There are over 160 road cycling routes available around Old Hill, catering to various skill levels. This includes 46 easy routes, 95 moderate routes, and 26 difficult routes, ensuring options for every cyclist.
Yes, there are several easy routes perfect for beginners or those looking for a more relaxed ride. One popular option is the Kneads Bakery – View of Saugatuck Reservoir loop from Westport, a 25.5-mile (41.0 km) trail that takes about 1 hour 48 minutes to complete and leads through varied landscapes. Another easy route is the Pequot Avenue (brand new surface) – Beachside Avenue - Great stretch to ride loop from Westport, which is 23.0 miles (23.0 km) long.
For experienced cyclists seeking a challenge, the area offers several difficult routes. The most popular is the View of Saugatuck Reservoir – Beachside Avenue - Great stretch to ride loop from Westport, a 62.1-mile (99.9 km) trail with significant elevation gain, typically taking around 4 hours 49 minutes to complete.
The road cycling routes around Old Hill are highly rated by the komoot community, with an average score of 4.7 stars from over 60 reviews. Cyclists often praise the varied terrain, challenging ascents, and scenic descents, as well as the options available for different ability levels.
Yes, the routes often pass through scenic areas. You might encounter highlights such as the Connecticut Gold Coast, offering beautiful coastal views, or the tranquil South Norwalk Reservoir. Some routes also go near historical sites like the Lockwood-Mathews Mansion Museum.
Many of the routes in the Old Hill area are designed as loops, allowing you to start and finish at the same point. For instance, the View of Saugatuck Reservoir – View of Saugatuck Reservoir loop from Westport is a moderate 43.3-mile (69.7 km) path that offers varied terrain with notable ascents and descents.
Hilly regions generally offer excellent cycling conditions during spring, summer, and autumn. These seasons provide pleasant temperatures and vibrant landscapes, from lush forests to open vistas. While winter cycling is possible, be prepared for potentially colder conditions and check local weather for road conditions.
Yes, some routes pass by convenient stops for refreshments. For example, the Kneads Bakery – View of Saugatuck Reservoir loop from Westport route starts near Kneads Bakery, a great spot for a pre-ride coffee or post-ride treat. Other routes may lead through towns with various cafes and pubs.
While the guide focuses on the Old Hill area, which is conceptually a hilly region, if you are referring to the West Midlands in the UK, public transport options for bikes can vary. It's always best to check with specific train or bus operators for their policies on carrying bicycles, as restrictions often apply during peak hours or for certain services.
Yes, for many road cycling routes, you can find parking options at common starting points or nearby towns. It's advisable to check the specific route details on komoot for recommended parking areas, especially for longer or more popular trails.
While many routes in this hilly region feature significant elevation changes, there are also easier options that could be suitable for families with older children or those comfortable with road cycling. Look for routes marked as 'easy' on komoot, such as the 23-mile Pequot Avenue (brand new surface) – Beachside Avenue - Great stretch to ride loop from Westport, which has less elevation gain.


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