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