Find the top rated fishing trails in Pittsfield, whether you're looking for an easy short fishing trail or a long fishing trail, you'll find what you're looking for. Click on a fishing trail below to find trail descriptions, trail maps, photos, and reviews.
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did trail 7 years ago. What a change!! Smooth all the way from Copake Falls to Wassaic!!!! Did 50 mile round trip then took a dip in the spring fed lake at Taconic Hills State park. Can walk to the lake from the trail head at copake falls. Also a nice state park with interesting sights. We stayed in Great Barrington , 10 miles from Copake Falls. Make sure you check out the Barrington Brewery. Great beer, great food.
I have ridden this trail from one end to the other! Parts are wonderful and parts washed out and muddy!
Love the scenery. There are plenty of rest areas.
Beautiful trail. Well maintained. Headed west from Henrietta first, a little secluded. Only went about 2 miles then headed east to lock 33. Felt safer going east. Full of exercise traffic… love to see that!
I rode this trail from the Northern tip south about 10 miles and back. It was very smooth pavement, a well marked trail and delightful views.
Rode it Friday. The views were beautiful, the trail was in great condition, and the road crossings were not a problem at all. I’ll definitely be riding this one again.
I just rode the trail from Cheshire to New Haven Harbor. It gets confusing because of the lack of signage once you go under the Temple St Garage in New Haven. You get dumped out into a street and don't know where to go. The trail is on the road or sidewalk depending on what you prefer. Take a left onto Grove St. continue to the end and take a right onto Olive ST. Follow Olive St. to the end and pick up the trail again on Water St. Cross Brewery ST and take a right to continue on Brewery. Brewery changes to Sargent Drive. Take a left to go under I95 and the water will be in front of you. If you take a right and continue down for a little, along the water's edge, you will find dozens of food trucks to buy lunch before a return trip. It was well worth the trip.
As of 6/3/25 this trail is still closed south of 11th street.
There is a detour indicated, which we tried to follow, but quickly lost track of.
Found another way to access the trail further south, only to realize that we'd gotten onto the part of the trail that was officially closed.
I'm sure this will warrant a higher rating once it has re-opened, but we were more than a bit disappointed today.
I’m not a trail master so take this with a grain of salt. I thought the trail was pretty good. I wanted a shorter trail with some scenery and this was good for exactly that. It was starting to rain so it cut my walk short however the trail was pretty well maintained with fresh wooden mulch to cover some of the wet areas. Not a lot of wildlife other than some birds, geese and butterflies. It was very peaceful and I will go back again
I rode the entirety of the Southwick Rail Trail coming from the Farmington Canal in CT. The Farmington is in very good condition, the Southwick is in even better condition! There are mile markers every mile, the scenery is very peaceful and the trail is very flat making it an easy ride. I stopped as soon as I hit the Columbia Greenway but it is also a seamless transition to that trail as well.
I didn't notice any places to pull off for food but its a short trail so I don't consider that a negative. The trails that join this one really give you so many options for ride length or to visit the trail towns along the way.
I rode the entire northern section of the Farmington Canal Trail from Plainville into MA on a windy Easter Sunday. The trail itself is fully paved, in very good overall condition (there are a few bumps and cracks but nothing major). Simsbury offers a great stopping off point to get refreshments just a quick turn off from the trail. The scenery changes from light industrial parks, residential, marshes, a little farmland and some nice wooded areas.
I have one complaint that prevents this from being a five star trail. The signage could be better. There are times in the more urban areas that I lost the trail, a quick look at Google Maps got me back on and I never was too lost. There are a few signs that were helpful so just a few more would make this a five star trail.
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