Explore the best rated trails in Great Barrington, MA, whether you're looking for an easy walking trail or a bike trail like the Albany-Hudson Electric Trail and Black Bridge Trail . With more than 59 trails covering 808 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 friend and I did this ride today starting from Brewster to Hopewell Junction, continuing on the Dutchess Rail Trail for ~4 miles and back. The ride was excellent, a little over 50 miles with a gradual decent (~10 miles) on the way to Hopewell and ascent back. The trail was very smooth, there were a couple of spots on the Dutchess side that had growth into the trail and one downed tree blocking the way.
Great ride through the shawingunk mountains ! Trail was great bikes were awesome ! What a beautiful day !!
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.
Beautiful ride in the am was nice and cool and quiet Down hill to hopewell This time of year there are so many raspberries on the side of the trail going back to collect some for jam end of the week Being a rail trail the way back is just a slight incline Great Ride
Beginning perhaps 2 miles north of the Simsbury Airport and continuing north for at least a few miles the trail will be closed for construction (looks like repaving + ?). I was on this trail yesterday and the "Will Be Closed" signs are abundant.
Rough in spots but really nice ride !!! Would do it again ! Tough around the steep hill x2 , Tressel bridge !!! But nice scenery and cool breeze Pat and Kevin B
Section from New Paltz (and maybe a mile or two below, I haven’t checked) to a mile or so north of the Rosendale Trestle is superb. Just after the Women’s Studio Workshop is an interesting historical furnace chimney. But then the trail comes apart - chunky gravel and hills I wouldn’t want to come down, leading to Williams Lake (saw lots of landscaping going on but no one using that end of it recreationally). I returned to the Women’s Studiovia the road.
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.
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