Explore the best rated trails in South Windsor, CT, whether you're looking for an easy walking trail or a bike trail like the Windsor River Trail and Niantic Bay Boardwalk . With more than 57 trails covering 480 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
We walked along the towpath section in Uxbridge and it was lovely. My daughter is in a wheelchair and it was doable, if not perfect. Park and enter from the Visitors' Center, and watch for the rocks and roots.
The Columbia Greenway Rail Trail is a beautiful rail trail that has a little of everything. City views, farmland, rivers, and tree cover in just 3 miles. The bridges are also a feature that make this trail unique. I love that it connects to trails that go much further south into CT, so whether you are just going for a short walk or a long ride you can do it here! Plenty of access points too (including 4 in downtown Westfield alone) make it easy to get on the trail from nearby neighborhoods or get off to shop and eat at downtown businesses.
I stopped on Wednesday on my way home to walk my dog. Very quiet during the week and a lovely walk if you like to listen to the water from the Connecticut river flowing by. You can see where the river has flooded, read the various historical statue plaques.
A sidepath has been constructed adjacent to Route 189 to Main St in Tariffville. Trail is now about 3 miles long. It will be designated as part of the East Coast Greenway and is visible on Google Street View.
After reading many of the mixed reviews for this trail on TrailLink, I decided to keep my ride short but sweet by restricting it to what seemed to be the most picturesque - the portion between the historic Unionville train depot and the Riverside Nursery and Garden Center in Collinsville.
This part of the trail contains breathtaking views of the officially deemed wild and scenic Farmington River. In addition, since I did this in mid October, the river was a perfect reflecting glass for the amazing fall colors.
My ride was only a total of twelve miles out and back, but I now have the most perfect photos, videos, and memories of this Connecticut treasure!
The bike ride is easy and mostly flat with lots of locals getting their steps in and exercising their dogs. Surprisingly, I only encountered two other bicyclists on my early weekday morning ride.
We love biking the Airline and have used non electric hybrid bikes as well as e-bikes. Both work well. On 10/28/2023 we biked the section from Willimantic parking at the Connecticut Eastern Railroad Museum area and pedaled to Rt. 207 Lebanon Rd, Amston, CT. FYI, we're in our 60s and encountered no difficulties with the terrain.
The path is nice and cool in the summer due to lots of shade. Much of it has large sections of big tree roots, though.
I rode the southern half of this trail from Millerton to Wasaic the first week in October on a 75° afternoon. Beautiful ride on a beautiful day.
Nice quiet ride to take time to enjoy these beautiful days.
Rode the 13 miles from Orphan Farm Rd to Millerton and back. At the northern end, at Orphan Farm Rd is a large parking area adjacent to a small farm, a solar panel field and a glamping site. No one there at 8am that Saturday but half a dozen cars upon my return at 11. Likewise, I had the trail practically to myself until I neared Millerton and found it moderately traveled by later that morning. The asphalt trail was in very good condition and there are a few boardwalk sections as well, also in very good condition. The environs are beautiful with forested sections, farm fields, wetlands and vistas of the nearby hills. Not more than two miles from the north end is the Depot Deli, near the entrance to Taconic State Park, where all manner of beverages, ice cream and snacks can be found. Breakfast at Oakhurst Diner in Millerton is highly recommended. Clean public bathrooms can be found just behind the schoolhouse museum beside the trail after crossing the main street.
We biked the trail today from Franklin and although it was a beautiful ride through the forest, our trip ended at the 4 mile mark because the path turned into a single lane rocky/sandy pathway. We traveled it briefly but it was not doable. It’s frustrating after reading from several apps and websites that it did not mention this. They all state it’s a 22 mile ride. Still had fun. Love getting out on our bikes!
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