Captain John Bissell Trail


3 Reviews

View Trail Map
View Map
Send to App

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Captain John Bissell Trail Facts

States: Connecticut
Counties: Hartford
Length: 4.5 miles
Trail end points: Charter Oak Greenway to Chapel Road at Burnham Street and Main Street to Windsor Meadows State Park
Trail surfaces: Asphalt
Trail category: Greenway/Non-RT
ID: 10497088

Captain John Bissell Trail Description

The Bissell name looms large in this part of New England, and has been immortalized in multiple ways, including the Bissell Ferry, the Bissell Memorial Bridge and now, the Captain John Bissell trail, after the man who started one of the US’s first ferry services in 1641, connecting Windsor to South Windsor across the Connecticut River.

Th Capt. John Bissell combines two segments totaling 4.5 miles off-street trail and 2.9 miles of on-street biking in South Windsor. Starting from southeast to northwest, the trail breaks off from another prominent greenway, the Charter Oak Greenway at the northwest corner of Veterans Memorial Park. The trail ducks under US 6, comes to the Hockanum River and the crosses under I-84 then winds up towards Middle Turnpike/ US 44. Crossing the turnpike, you’ll find the trail is wider and better maintained. It parallels Interstate 291 for a spell, then crosses underneath and across a railroad to bring you to the Tolland Turnpike. There’s a crosswalk that you can take to reach Chapel Road and the trail continues up to Burnham St. However, past this point, to continue northwest, you’ll have to bike on Chapel Road as there is only a sidewalk here. Fortunately Chapel Road is a low traffic road, but of course, take precautions when riding on-street. Stay on Chapel Road for 2.4 miles, then make a left onto Main Street for another half mile. Just before you get to 291, the off-road trail restarts on your right and parallels the highway for 1.4 miles, crossing over the Connecticut River on the Bissell Bridge. Once you are in Windsor, the curves under the highway to the trailhead at Windsor Meadow State Park. Here on the riverbank, you can also find the entrance to the Windsor River Trail.

Parking and Trail Access

Park at the Windsor Meadows State Park parking area at 265 E Barber St, Windsor, CT. 

Captain John Bissell Trail Reviews

well I did it

This is probably great for commuters of to get across the river but that’s about it. Poorly marked and poorly maintained. Lots of glass on the path portion. No historical markers or any other information that I noticed.

Capt. Bissell Need signage

Took off from Silver Lane on the Charter Oak Trail to get started. 1/2 mile take a right to get on this trail. The surface is ok but showing a lot of grass in the frequent pavement cracks. Woody vegetation is leaning into the trail. The trail twists and turns. There are many places where the visibility is poor especially on faster down hill areas. Mowing back everything would help. Most problematic is the very poor signage. With all the changes in direction improved signage on this trail is a must.

Great hard surface trail, light-traffic roads

We love all of Main St, South Windsor, and it's perfect for a bike ride. I recommend starting at the top of Main St rather than by Chapel Rd as suggested here. It's a sample of old New England with lots of well-maintained vintage homes (including the birthplace of Jonathan Edwards), tobacco barns, fields, & farms. The road itself is a very moderate incline, similar to rails-to-trails. The bike trail alongside I291 is also very easy biking. We only had time to go about halfway on that portion before we needed to head back. An absolutely perfect ride!

Nearby Trails

Go Unlimited Today!

  • FREE Account
  • View over 40,000 miles of trail maps
  • Post your trail reviews
  • Share your trail photos
  • Save your favorite trails
  • Learn about new trails near you
  • Get a free map in the app!
Register for FREE
Purchase Unlimited

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple


Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple


Your account has been deleted.