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Routes
Road cycling routes
United States
Connecticut
Capitol Planning Region

Windsor Meadows State Park to Windsor Locks loop via Captain John Bissell Trail

Routes
Road cycling routes
United States
Connecticut
Capitol Planning Region

Windsor Meadows State Park to Windsor Locks loop via Captain John Bissell Trail

Easy

2.7

(4)

26

riders

Windsor Meadows State Park to Windsor Locks loop via Captain John Bissell Trail

01:55

46.9km

210m

Road cycling

Easy 29.1-mile road cycling loop from Windsor Meadows State Park, featuring river views and historic New England scenery.

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

Get Directions

1

1.80 km

Captain John Bissell Trail Bridge

Highlight (Segment) • Bridge

The Captain John Bissell Trail is a popular multi-use trail that connects Hartford and East Hartford.

There are two sections of trail: one is 4.5 miles long and the other …

Tip by

2

18.0 km

The Barn Yard Bridge

Highlight • Bridge

This cute covered bridge was built to showcase the craftsmanship of The Barn Yard, who build all manner of timber based outbuildings. Set over a little bubbling brook, keep an eye out for it as you ride on by.

Tip by

3

25.2 km

Broad Brook Millpond

Highlight • Lake

The Broad Brook Millpond was originally utilized to power a mill in the industrial era, but is now surrounded by residential homes. A historic opera house stands by the brook …

Tip by

4

36.0 km

Quiet road along the Connecticut River

Highlight (Segment) • River

no lights and shoulder is decently wide. Not a lot of cars

Tip by

B

46.9 km

End point

Parking

Loading

Way Types & Surfaces

Way Types

34.5 km

5.54 km

4.56 km

2.33 km

Surfaces

44.7 km

1.97 km

286 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 (80 m)

Lowest point (10 m)

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Weather

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Thursday 28 May

23°C

14°C

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This route was planned by komoot.

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Frequently Asked Questions

How difficult is this cycling loop?

This route is generally considered easy for road cycling. It features a hard, paved surface with minimal elevation gain and descent, making it suitable for most riders. While some older sections might have minor wear, the overall experience is smooth.

What is the terrain like on this route?

The route primarily uses a hard, paved surface, with many sections resembling a rails-to-trails conversion. You'll find very moderate inclines or flat stretches, ideal for easy biking. Some parts are off-street paths, while others are on low-traffic roads like Chapel Road and Main Street in South Windsor.

What scenic views or landmarks can I expect?

You'll enjoy varied scenery, including picturesque views of the Connecticut River, especially from Windsor Meadows State Park and the Captain John Bissell Trail Bridge. The route also passes through an 'old New England' setting with vintage homes, historic sites, tobacco barns, fields, and farms in South Windsor. You'll also cross the The Barn Yard Bridge and pass by Broad Brook Millpond.

Does this route connect to other trails?

Yes, this route is a crucial link in the regional trail network. It connects to the Charter Oak Greenway and the Windsor River Trail. You'll also find sections of the Windsor Locks Canal State Park Trail, Main Street Sidepath, South Windsor Estates Walkway, and Windsor Center River Trail along the way.

Where can I park to access this cycling loop?

The loop typically begins and ends at Windsor Meadows State Park, which offers convenient access to the trailhead. Parking is generally available there.

Is this cycling route dog-friendly?

While the route is primarily for cycling, specific dog policies can vary by section. For example, the Windsor Locks Canal State Park Trail generally allows leashed dogs. It's always best to check local regulations for each specific park or trail section you plan to visit with your dog.

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

The best time to cycle this route is generally during the spring, summer, and fall months when the weather is mild. The varied scenery, including river views and historic landscapes, is particularly enjoyable during these seasons. Be mindful of potential reduced visibility in twisty downhill areas during periods of overgrown vegetation.

Are there any permits or fees required for this route?

No, there are typically no permits or entrance fees required to access or cycle this route, including Windsor Meadows State Park or the Captain John Bissell Trail sections.

Is this route suitable for families?

Given its easy difficulty, paved surfaces, and minimal elevation changes, this cycling loop is generally suitable for families. However, some sections are on low-traffic roads, so adult supervision is always recommended, especially with younger riders.

Are there places to eat or drink along the route?

The route passes through areas like South Windsor and Windsor Locks. While the trail research doesn't explicitly list cafes or pubs directly on the trail, you will find amenities and establishments in these towns that are easily accessible from the route.

What is the historical significance of the Captain John Bissell Trail?

The trail is named after Captain John Bissell, who established one of the first ferry services in the United States in 1641, connecting Windsor to South Windsor across the Connecticut River. The route's crossing of the Connecticut River via the Bissell Bridge Walkway highlights this historical connection.

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