Charter Oak and Captain John Bissell Trail Loop
Charter Oak and Captain John Bissell Trail Loop
3.4
(2)
83
riders
02:00
34.4km
150m
Cycling
Cycle the easy 21.4-mile Charter Oak and Captain John Bissell Trail Loop, featuring river views, forests, and urban landscapes.
Last updated: February 26, 2026
Waypoints
Start point
Parking
Get Directions
4.31 km
Highlight (Segment) • Bridge
Tip by
15.9 km
Highlight (Segment) • Cycleway
Tip by
34.4 km
End point
Parking
Way Types & Surfaces
Way Types
18.1 km
6.58 km
5.63 km
3.83 km
295 m
Surfaces
22.8 km
11.5 km
< 100 m
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Elevation
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Weather
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Today
Thursday 28 May
24°C
14°C
35 %
Additional weather tips
Max wind speed: 22.0 km/h
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This route was planned by komoot.
The route primarily features paved multi-use paths, making it suitable for touring bicycles. However, you will encounter some on-road sections, particularly along Chapel Road in South Windsor, which has a narrow shoulder but generally low traffic. Be aware that parts of the Captain John Bissell Memorial Bridge Trail may have pavement cracks and overgrown vegetation in places.
This touring cycling loop is approximately 34.4 km (21.4 miles) long. Most cyclists can expect to complete it in about 2 hours, depending on their pace and how often they stop to enjoy the scenery.
While the route is rated as 'easy' by komoot, the presence of some hilly sections, including 'short and (relatively) steep' climbs on the Charter Oak Greenway, and on-road segments, means it's best suited for cyclists with some experience or those comfortable with moderate effort. Families with younger children might find some sections challenging due to the hills and traffic on road segments.
The loop offers diverse scenery, from college campuses and community parks to forested areas and riverfront views near the Connecticut River. You'll pass through tobacco and corn fields in South Windsor and experience urban environments in Hartford, with opportunities to see skyscrapers and artwork near Mortensen Riverfront Plaza and Bushnell Park. Don't miss the Captain John Bissell Memorial Bridge, which crosses the Connecticut River.
Yes, this route is a significant part of the larger East Coast Greenway network. It also incorporates sections of the Captain John Bissell Trail, Charter Oak Greenway, Riverside Park Trail, and the East Coast Greenway (CT), among others. It provides connections to regional trails like the Windsor River Trail and the Hop River State Park Trail.
While specific parking areas are not detailed, you can typically find public parking near access points in towns along the route, such as Hartford or South Windsor. Look for parking facilities near parks or trailheads that connect to the Charter Oak Greenway or Captain John Bissell Trail.
Spring and fall generally offer the most pleasant cycling conditions with mild temperatures and beautiful foliage. Summer can be enjoyable, but be prepared for warmer weather. Winter cycling is possible, but conditions may vary, with potential for ice or snow on paths, and some sections might have reduced visibility due to overgrown vegetation.
Generally, dogs are allowed on multi-use trails like the Charter Oak Greenway and Captain John Bissell Trail. However, they must be kept on a leash at all times, and you are responsible for cleaning up after your pet. Always check local regulations for specific sections of the trail you plan to visit.
No, there are no permits or entrance fees required to access and cycle the Charter Oak and Captain John Bissell Trail Loop. It is a publicly accessible trail system.
Yes, as the route passes through urban areas like Hartford and various towns, you'll find numerous options for cafes, pubs, and accommodation. The Hartford city center, in particular, offers a wide range of amenities for cyclists looking to refuel or stay overnight.
Beyond the Connecticut River views, you can expect to see forested areas, including a white pine tree forest, and pass by Bolton Notch Pond. The agricultural sections in South Windsor with tobacco and corn fields also offer a distinct natural landscape.