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Routes
Bike touring routes & trails
United States
Connecticut
Western Connecticut Planning Region
Old Greenwich

Greenwich, CT to Bedford, NY loop

Hard

4.9

(8177)

8,178

riders

Greenwich, CT to Bedford, NY loop

03:29

52.5km

600m

Cycling

This difficult 32.6-mile touring cycling loop from Greenwich, CT to Bedford, NY offers challenging climbs and picturesque views.

Last updated: February 26, 2026

Waypoints

A

Start point

Train Station

Get Directions

1

3.53 km

St. Catherine of Siena Church

Highlight • Religious Site

This church was the last one designed by famed architect Gustave E. Steinback who made his name designing churches across New York City & Chicago.

Tip by

2

16.6 km

Viewpoint and Rock Wall on Taconic Road

Highlight (Segment) • Viewpoint

Elevated clearing with nice view and a rock wall(one of many in the area) on a relatively quiet road

Tip by

3

21.4 km

St Mary's Church

Highlight • Religious Site

I would recommend E Middle Patent Road as a nice and quiet road for road biking or touring. The church is not that noteworthy imho.

Tip by

4

27.4 km

Bedford Village Historic District

Highlight • Historical Site

Thanks to over a century of dedicated work by the Bedford Historical Society this town has a number of well preserved buildings plus multiple museums and education programs for locals & tourists alike.

Tip by

5

30.8 km

Mianus River Gorge

Highlight • Gorge

Nice hilly and shady road but watch for pot holes

Tip by

B

52.5 km

End point

Train Station

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Way Types & Surfaces

Way Types

32.1 km

19.6 km

763 m

< 100 m

Surfaces

27.4 km

20.9 km

4.02 km

265 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (180 m)

Lowest point (0 m)

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Weather

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Today

Saturday 23 May

15°C

11°C

92 %

Additional weather tips

Max wind speed: 20.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How long does it typically take to complete the Greenwich, CT to Bedford, NY loop?

This challenging touring bicycle loop is approximately 52.5 kilometers (about 32.6 miles) long. With a duration of around 12,533 seconds, or roughly 3 hours and 29 minutes, it's designed for experienced cyclists. Keep in mind that this estimate doesn't include stops for breaks or sightseeing.

What is the difficulty level and terrain like for this cycling route?

The Greenwich, CT to Bedford, NY loop is classified as difficult and requires very good fitness due to its significant elevation gain of nearly 600 meters (about 1,968 feet). The terrain is primarily paved, making it suitable for touring bicycles, but expect numerous climbs and descents throughout the ride.

What are the scenic highlights along the Greenwich, CT to Bedford, NY loop?

While the route itself offers picturesque views of the region, notable points of interest include the historic St. Catherine of Siena Church and St Mary's Church. You'll also pass through the charming Bedford Village Historic District and near the Mianus River Gorge. Don't miss the Viewpoint and Rock Wall on Taconic Road for a great vista.

Where can I park to access this cycling loop?

Specific parking details for the start of this exact loop are not provided, but cyclists often look for public parking in areas like Greenwich, Stamford, or Bedford. It's advisable to check local municipal websites, such as greenwichct.gov, for information on public parking facilities in Greenwich that accommodate cyclists.

What is the best time of year to cycle the Greenwich, CT to Bedford, NY loop?

The best time to cycle this route is typically during the spring and fall months when the weather is milder and the scenery is vibrant with new growth or autumn colors. Summer can also be pleasant, but be prepared for potentially higher temperatures and humidity. Always check the weather forecast before heading out.

Are dogs allowed on this cycling route?

This route is primarily on paved roads and passes through various towns and areas. While dogs are generally not suitable companions for a long, difficult touring bicycle ride on roads, specific regulations for dogs would depend on local ordinances in Greenwich, Stamford, and Bedford, and any parks or preserves you might briefly pass through. It's best to assume this route is not ideal for cycling with dogs.

Are there any permits or fees required for this cycling loop, especially for Mianus River Gorge Preserve?

For the cycling loop itself, which primarily uses public roads, no specific cycling permits are generally required. However, if you plan to explore the Mianus River Gorge on foot, it's important to note that while there are no entrance fees, the preserve has specific regulations regarding visitor conduct to protect its natural environment. Always check the preserve's official website for the most current rules before visiting.

Does this route connect with other cycling trails?

Yes, this touring bicycle route briefly intersects with several other paths. You'll find sections that overlap with the East Coast Greenway (CT), Old Farmland Trail, Todd Pond Trail, Blue/Red Trail, Blue/Green/Red Trail, River Trail (Green), Green Trail, Interpretive Loop (Purple), and River Overlook. These are typically short segments where the route shares a path with these named trails.

Are there places to eat or get refreshments along the way?

Yes, as the route passes through several towns including Greenwich, Stamford, and Bedford, you will find opportunities for refreshments. Bedford Village, in particular, is known for its well-preserved historic district and likely offers cafes or eateries where you can refuel.

What should I pack for this challenging touring bicycle ride?

Given the route's difficulty and length, a comprehensive packing list is essential. You should bring plenty of water, energy snacks, a repair kit for your bicycle (including spare tubes and a pump), a first-aid kit, and appropriate cycling attire for varying weather conditions. A helmet is mandatory, and consider bringing a phone for navigation and emergencies.

Is this cycling route suitable for beginners or families?

No, this specific Greenwich, CT to Bedford, NY loop is classified as difficult and requires very good fitness due to its significant elevation gain. It is not recommended for beginners or families with young children. More experienced touring cyclists looking for a vigorous ride will find it rewarding.

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