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The 5 Best Trails for Bicycling in Connecticut

Here's what you need to know...
  • Cycling through Connecticut is one of the best ways to enjoy the incredible climate and to immerse yourself in nature
  • Cyclists should take extra precautions to stay safe while traveling on Connecticut roads
  • The right combination of safety gear can help you to stay safer while riding your bicycle on all road and trail conditions
Driving a car may be a relatively fast and convenient way to get from one location to another, but many people prefer to take the slower method of riding a bike.

When you ride a bicycle through beautiful Connecticut landscapes, you can immerse yourself in nature while also promoting your own health and well-being through excellent physical activity. This type of activity is also great for the environment, and it can help you to save money on fuel and other auto expenses.

This type of activity is also great for the environment, and it can help you to save money on fuel and other auto expenses. Many people also enjoy a sense of camaraderie or community with other cyclists that you cannot experience when you travel in a car.

Each bicyclist enjoys a unique experience on scenic trails, but many will agree that a great bicycle  trail shares at least a few of the same qualities.

The best routes to cycle on are relatively flat and fast, and they are well-paved or well-maintained with minimal bumps or divots. Some cyclists enjoy twists and turns on their routes, and climbs and descent can add a challenge to any cycling experience.

Before you plan your cycling trip make sure you have the best auto coverage with our free quote tool above!

The 5 Best Trails for Bicycling in Connecticut

In Connecticut, you can find stunning natural beauty as well as numerous trails that meet these guidelines in different ways.

If you are planning to venture out on your bicycle in Connecticut and are looking for a great place to ride, consider some of these popular routes.

#1 Ridgefield Rail Trail

Length: 2.3 miles
Best Feature: Wide trail made out of crushed cinder

The Ridgefield Rail Trail is a 2.3-mile long route that takes you from the downtown Ridgefield area to the Branchfield area a short distance away, and it follows along the path of an old rail line.

This trail is most commonly used for walking and running as well as for cross country skiing in the winter months, so you should keep your eyes open for pedestrians as you cruise along the path.

The trail is six to eight feet wide in most places, and it is made out of crushed cinder that is easy to ride on. This makes it convenient for you to safely navigate around pedestrians. The primary amenities along this trail are benches and mile markers.

#2  Monroe Housatonic Paul Trail

Length: 5 miles
Best Feature: A flat trail with ample shade from large trees

The Monroe Housatonic Paul Trail begins at Great Hollow Lake Park, and it takes you away from town on a five-mile path that is wide in most areas. This is a relatively flat and well-maintained trail that is ideal for biking on.

You will pass through heavily wooded areas as well as by a few water features that add stunning beauty to the landscape.

Several picnic areas are located in strategic areas along the trail, and these give you a great place to stop and enjoy a snack or meal when you need to take a break.

#3 Middlebury Greenway

bicycle-1834265_1920-1600x1600Length: 4 miles
Best Feature: Wildflowers, a pond, a lake

The Middlebury Greenway takes you on a scenic, four-mile journey from the Waterbury town line to the Woodbury town line. The trail is a converted former trolley bed, and it is now covered with fine stone dust, creating ideal riding conditions for you to enjoy with a leisurely ride close to town.

This route will take you by the Quassy Amusement Park, Bristol Park, Lake Elise, Fenn Pond, and several other points of interest. Notably, the Walk for the Greenway community event is held along this trail every April.

#4 Kress Family Trail

bike-966771_1920-1600x1600Length: 2.5 miles
Best Feature: Orzech Family Preserve

If you are looking for a scenic place to cycle through the Connecticut countryside, the Kress Family Trail is an excellent option to consider. This trail is 2.5-miles in one direction, and it takes you along an old rail line near the Shepaug River.

You will enjoy a relatively flat trail that is also used for cross-country skiing in the winter months.

The path also takes you by pastures as well as rolling hills to provide you with excellent natural views to enjoy during your ride.

#5 Larkin State Park Trail

Length: 10.3 miles
Best Feature: Old railroad trail with excellent inclines

The Larkin State Park Trail is a wonderful trail that follows along an old railroad line that was heavily used in the 1800s. This trail has one of the steepest inclines in the state for railroad lines, so it can be relatively challenging to maneuver on a bike.

With its elevation change and distance, this may be one of the most challenging routes on this list.

You can expect to see ample trees, valleys, wetlands, horse farms, and several other scenic features along the way.

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Considerations for Drivers on Roads Regularly Used by Cyclists

While you may be a cyclist who actively enjoys riding on some of the most scenic trails in the state, you also may find that some cyclists enjoy traveling on roads with vehicles.

This means that you must share the road and drive courteously. It also means that you need to review your car insurance to ensure that you have the right type of coverage for a possible bicycle accident.

If you are driving in your car in Connecticut and hit a cyclist, you may be held legally responsible for all property damage, medical expenses, and other related expenses that you cause.

The state requires all drivers to have a minimum amount of liability insurance, which will pay for those expenses up to the coverage limits.

You will need a comprehensive insurance policy if you want coverage that pays for your expenses if you collide with a cyclist.

Comparison shopping is a great way to identify the best deal on the auto coverage you need in Connecticut.

Safety Tips for Riding Bicycles

AdobeStock_72047239-1600x1600 (1)If you plan to ride on a bicycle in Connecticut or in any other areas, you should follow a few safety tips. This includes:

You can easily comparison shop online today with our free quote tool below before your next big cycling trip to find an affordable rate on your coverage.

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