4.4
(20)
862
riders
128
rides
Road cycling routes around Pemberwick, located in Greenwich, Connecticut, navigate a landscape characterized by lush greenery, tranquil ponds, and tree-lined roads. The area offers a mix of suburban and natural settings, with routes often passing through quiet, wooded sections and alongside water features like the Byram River. While Pemberwick itself is a neighborhood, its proximity to Greenwich's broader cycling network provides access to well-paved surfaces and varied terrain, including gentle rolling hills.
Last updated: July 10, 2026
24
riders
63.4km
03:04
570m
570m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
18
riders
57.9km
02:44
620m
620m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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17
riders
50.4km
02:27
600m
600m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
17
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
15
riders
59.4km
02:49
680m
680m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Pemberwick
This is a beautiful reservoir on a road which is gravel for about 2 miles and asphalt otherwise. Along the reservoir there is a grassy very small park with two benches which is a nice place to stop.
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The Bedford Oak is one of those rare living landmarks that quietly connects the past to the present. Estimated to be over 500 years old, this massive white oak has stood through centuries of change in Bedford, from Native American times to the Revolutionary War and beyond. Locals have always held it in high regard, and when development threatened its space in the 1970s, the community stepped up to save it. Thanks to their efforts, the tree and the land around it are now protected and cared for.
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Nice view of Long Island sound on Forest Ave (small inlet between houses).
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There is a gap in the properties here giving an excellent view of Long Island Sound. If you step off the bike there is a small grassy area to take a break.
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The views from this fast flowing and good quality road are lovely. With trees and quiet fields around you will gain a feeling of inner peace cycling along it.
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Although the church is not particularly noteworthy, the road running along it is a joy to cycle on with lovely views and little traffic.
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The Bedford Oak is a majestic oak that lives at the corner of Hook Road and the old Bedford Road (now Cantitoe Street) and is believed to be over 500 years old.
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Round Hill Community Church is your very typical white boarded American christian church. It is really quite beautiful and may provide some spiritual salvation for you if you have time to get off your bike for five minutes.
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Pemberwick and its surrounding Greenwich area offer a wide selection of road cycling routes. You can find over 120 routes, catering to various skill levels, from easy loops to more challenging rides.
The road cycling routes around Pemberwick are characterized by lush greenery, tranquil ponds, and tree-lined roads. You'll encounter a mix of suburban and natural settings, with well-paved surfaces and gentle rolling hills, offering a scenic and varied riding experience.
The komoot community highly rates the road cycling experience in Pemberwick, with an average score of over 4 stars. Cyclists often praise the quiet, scenic roads, the beautiful natural features like ponds and woodlands, and the variety of routes available for different abilities.
Yes, Pemberwick offers several easy road cycling routes perfect for beginners or those looking for a relaxed ride. For example, the Bruce Park – Bruce Park Drive - Quiet Road loop from Greenwich is an easy 15.3-mile (24.6 km) trail that provides a peaceful ride through a quiet road loop.
For experienced cyclists seeking a challenge, Pemberwick's broader network includes more demanding routes. The Titicus Reservoir South Side – Cross River Reservoir loop from Port Chester is a difficult 73.1-mile (117.7 km) route with significant elevation gain, offering a rigorous and rewarding ride.
While cycling around Pemberwick, you can enjoy various natural features. The area is known for its proximity to the Byram River and features like The Pond at Caroline Place. Routes may also pass by areas with lush greenery and wooded sections. You might also encounter highlights such as Cranberry Lake or the Mianus River Natural Park.
Beyond natural beauty, you might find points of interest like Greenwich Point Beach or St. Catherine of Siena Church, depending on the route you choose. These offer opportunities for a brief stop and exploration.
Pemberwick's gentle rolling hills and quiet roads make it suitable for family-friendly cycling. Many of the easier routes, particularly those that stick to less trafficked areas or pass near parks like Pemberwick Park, can be enjoyable for families. Always check the route details for distance and elevation to ensure it matches your family's ability.
Yes, many of the road cycling routes around Pemberwick are designed as loops, allowing you to start and end at the same point. Examples include the Milbank Conservation Easement – Round Hill Community Church loop from Port Chester and the Byram River Marina – Byram Lake Reservoir loop from Port Chester.
For road cycling routes in and around Pemberwick, you can often find parking near local parks or designated public areas. Pemberwick Park itself offers facilities. For more information on parks and facilities in Greenwich, you can visit the official Greenwich Parks & Recreation website.
The spring and fall seasons generally offer the most pleasant conditions for road cycling in Pemberwick, with mild temperatures and beautiful foliage. Summer can also be enjoyable, though it may be warmer. Always check local weather forecasts before heading out.


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