Greenwich, CT to Bedford, NY loop
Greenwich, CT to Bedford, NY loop
4.9
(8177)
8,178
riders
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
Start point
Train Station
Get Directions
3.53 km
Highlight • Religious Site
Tip by
16.6 km
Highlight (Segment) • Viewpoint
Tip by
21.4 km
Highlight • Religious Site
Tip by
27.4 km
Highlight • Historical Site
Tip by
30.8 km
Highlight • Gorge
Tip by
52.5 km
End point
Train Station
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
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.