Explore the best rated trails in Waterbury, CT, whether you're looking for an easy walking trail or a bike trail like the Walkway Over The Hudson and Windsor River Trail . With more than 60 trails covering 458 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.
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.
After pedaling down the Hudson Valley Rail Trail from New Paltz, I made my way onto the walkway. It was 7:30 on a brisk mid October weekday morning, and the bridge was not crawling with hordes of tourists (like me). Instead it was obviously primarily locals out jogging, getting their steps in on their walks, rollerblading, and walking their dogs.
The views are as expected - absolutely sensational and breathtaking looking both up and downriver.
After continuing across I proceeded to explore the Dutchess Rail Trail for several miles before heading back.
As luck would have it, when I returned the walkway was a completely different world. It was totally enveloped in fog, and you could no longer see the Hudson let alone fifty yards in front of you. The bridge was essentially deserted. Worst of all, I didn't get to do my selfies with a Hudson River background!
The walkway, combined with the rail trails on either end, is a must destination ride for bicyclists. What an unforgettable experience!
In my quest to bicycle in all fifty states, I drove 2,800 miles in order to ride my bike on this rail trail. It's hard to elaborate upon the Rails-To-Trails description. It was exactly as advertised and an absolute joy to experience on a brisk fall morn in early October.
About all I can add is the trail is flat, plenty wide, in excellent condition, and is a fun ride in autumn as the leaves are changing color and fluttering down to transform the path's hue from black to golden brown. There's also plenty of railroad memorabilia here and there to enhance the ride.
I didn't drive nearly 3,000 miles to just ride a seven mile trail. Naturally I continued on across the Walkway Over The Hudson and then on to the Dutchess Rail Trail for a fuller experience of the Hudson Valley! It was all exactly as I had hoped it would be!
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.
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.
This is still a great trail but currently (9/2023) the Trailway is closed between the Stormville parking area on South Green Haven Road and the road crossing at Depot Road due to a partial washout (see pic).
There is a bypass using Route 216 (busy and not always good shoulders).
People have gone around the barricades and used the Trailway. Please use caution if you do so.
Parked on the east side of the bridge after a bit of confusion finding the end of the bridge. Signs were a bit confusing. We just looked at the huge bridge went towards the obvious end of it to find parking. Lightly crowded on a Monday morning around 9:30 as we headed west across the bridge. Well worth the trip as the views of the Hudson Valley are spectacular! Rode 8 miles west out into central New York. Very little elevation change and a clean smooth trail. Worth the ride!
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.
Very nice 7 miler tonight just before sundown. Trail was very clean and only lightly populated as we headed south for 3 1/2 miles and then back to the parking lot.
Too bad that Daddy O's had closed their kitchen when we returned. Had to go to the Redline Diner to get a post-ride meal on a Sunday night.
Road crossings were well marked and use automatic yellow flashing lights for traffic to be aware of bikers approaching the crossing. A nice feature.
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