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Routes
Bike touring routes & trails
United States
Connecticut
Capitol Planning Region

Charter Oak and Captain John Bissell Trail Loop

Easy

3.4

(2)

83

riders

Charter Oak and Captain John Bissell Trail Loop

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

A

Start point

Parking

Get Directions

1

4.31 km

Captain John Bissell Memorial Bridge

Highlight (Segment) • Bridge

A popular trail north of Hartford that begins at Windsor Meadows State Park and leads across Captain John Bissell Memorial Bridge to Main Street. This trail offers a beautiful mix of forest immersion and riverside views.

Tip by

2

15.9 km

Charter Oak Greenway

Highlight (Segment) • Cycleway

The Charter Oak Greenway is a 16 mile paved path through Hartford and its suburbs. The path traverses a wide range of places, including college campuses, parks, forests, riverfront, and the city center.

Tip by

B

34.4 km

End point

Parking

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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

Elevation

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

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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.

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Frequently Asked Questions

What is the terrain like on this touring cycling route?

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.

How long does it typically take to complete the loop?

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.

Is this trail suitable for beginners or families?

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.

What can I see along the route?

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.

Does the route connect to other well-known paths?

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.

Where can I park to access the Charter Oak and Captain John Bissell Trail Loop?

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.

What is the best time of year to cycle this loop?

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.

Are dogs allowed on the Charter Oak and Captain John Bissell Trail Loop?

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.

Do I need a permit or pay an entrance fee to cycle this route?

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.

Are there any cafes, pubs, or accommodation options near the trail?

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.

What are some natural features I might encounter?

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.

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