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Routes
Road cycling routes
United States
Connecticut
Western Connecticut Planning Region

Old Hill

The best road cycling routes around Old Hill

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.

Best road cycling routes around Old Hill

  • The most popular road cycling route is View of Saugatuck Reservoir – View of Saugatuck Reservoir loop from Westport, a 43.3 miles (69.7…

Last updated: June 30, 2026

43

riders

#1.

Kneads Bakery – View of Saugatuck Reservoir loop from Westport

41.1km

01:49

270m

270m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Popular around Old Hill

Hiking around Old Hill

Cycling around Old Hill

Running Trails around Old Hill

Tips from the Community

Stefano
July 5, 2025, Cranbury Park

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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Matthew
May 8, 2025, Camp Tepee

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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Zachary
January 24, 2025, Streets Pond

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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Scott
February 29, 2024, Pear Tree Point Cove

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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Frequently Asked Questions

What kind of terrain can I expect on road cycling routes around Old Hill?

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.

How many road cycling routes are available in the Old Hill area?

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.

Are there any easy or beginner-friendly road cycling routes?

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.

What are some challenging routes for experienced road cyclists?

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.

What do other road cyclists say about the routes in Old Hill?

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.

Are there any scenic viewpoints or attractions along the road cycling routes?

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.

Are there any circular road cycling routes available?

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.

What is the best time of year for road cycling in this hilly region?

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.

Are there places to stop for refreshments like cafes or pubs along the routes?

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.

Is public transport available for cyclists in the West Midlands area?

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.

Can I find parking near the road cycling trails?

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.

Are the road cycling routes suitable for families?

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.

Most popular routes around Old Hill

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