Looking for a great trail near New Fairfield, Connecticut? AllTrails has 5 great hiking trails, trail running trails, forest trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around Hudson Highlands State Park or Bear Mountain State Park, we've got you covered. You'll also find some great local park options, like Town Park. Ready for some activity? There are 3 moderate trails in New Fairfield ranging from 1.8 to 4 miles and from 436 to 1,187 feet above sea level. Start checking them out and you'll be out on the trail in no time!

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New Fairfield, Connecticut Map
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hiking
2 days ago

I love trying new trails and this was pretty close to home. I found it very hilly and narrow with many trees down and lots of rock scrambles as a result. The lake views were very pretty and must be breathtaking in the Fall. I came mid September, so the lake was quiet for the most part. It was actually just what I was looking for today! My pup and I had a great hike with lunch on a rock by the lakes edge. Would not bring young kids or someone even slightly unsure of their footing, as there are some very steep declines.

hiking
21 days ago

Nice little trail with dogs allowed.

hiking
2 months ago

This trail is beautiful, but the 2nd half (red) is very poorly maintained. Much over growth, downed trees, and narrow walkways. Go venture, but be warned!! Council Rock is worth the trip!!

hiking
2 months ago

Easy hike

hiking
over grown
2 months ago

easy to make into a longer Loop with various options colon using the Fire Road and the blue and yellow trails.

walking
3 months ago

We found this last minute, and weren't disappointed. Cute little trail, great for dogs, very lightly trafficked. if you're looking to not see many people at all. I suggest this.

hiking
3 months ago

This is a great trail for hikers of most abilities! limited steep points and very dog friendly. Starting from the pine hill parking lot go right at the first fork then follow anyway you please until you find the sign for the blue trail! Has been almost completely cleared since the tornado

hiking
muddy
3 months ago

This trail is great and provides lots of bridges crossing rivers but make sure to carry 6 large sticks at all times because at certain points of the trail it is covered in mud so use the sticks to make a makeshift bridge 2 sticks wide

hiking
muddy
4 months ago

hiking
muddy
rocky
4 months ago

nice walk, steep climb to the beautiful view. definitely avoid sneakers. need ankle support. will explore other trails here

hiking
8 months ago

We park on the side of the road by the fire road access (not possible during busy season) about a mile in on the fire road there is the blue trail trail head. The blue trail is about .75 mile but steep. Do not attempt in sneakers!! The climb pays off with a magnificent viewpoint looking out over candle wood lake. We had our dog off leash (always carrying one for passing other hikers) we will do this trail again (3.25 miles total)

hiking
9 months ago

Extended this loop out to the Fire Road....from the overlook spot followed the blue blazed trail to Fire Rd. View from rocks is beautiful. Overall this extended loop was great..passed several waterfalls and had nice views of Squantz pond.

Sunday, August 26, 2018

The NY section is outstanding. In August no readily accessible crossing of water to complete the loop outlined here - had to back track. Wear waterproof hiking boots and tick repellant. Mosquitoes will be an issue for some. CT portion is lovely, but overgrown with grass and weeds - be prepared for scratches and wet clothes. Inconsistently maintained mud crossings that are often in a weird place. Lots of downed trees, but trails are passable. Trail markings are very Connecticut- too few in some spots, but pretty. Lots of furniture and unusable human structures (cabin-like almost lean-tos that can fit only a small child). Bird boxes, bat boxes along trail. Not a lot of bird calls or small wildlife in evidence, though. Not a wide variety of flowering plants (grass instead). It’s beautiful. Perhaps if more people kick a buck in the donation box at the trail head some trail maintenance can be performed. For instance managing the tulip poplar saplings that will surely choke each other out and create problems for those that survive; re-align and repair the mud crossing; clean-up the liquor bottles on the CT portion; update the trail map. It’s rated as moderate, but it’s more on the easy end of the spectrum. Children can handle it, if they can walk a fair distance, have appropriate footwear and an adult moves the prickers out of the way. If the child is not comfortable outdoors, this walk/hike might not be fun during portions. There are picnic tables randomly placed along the trail. Dog loved it. People were arriving as we were leaving on a weekend morning. I bet it gets crowded. Crushed phone battery. Crushed. Bring a portable power supply or turn off. Crushed. A full battery. Having to back track makes the hike little longer. Pleasant walk. Enjoy.

hiking
Monday, August 06, 2018

Really nice trails around a beautiful nature preserve, with an abundance of streams and waterfalls. I walked the entire loop with the exception of the trail up to Hardscrabble Road. It was just too hot and I didn't have time. Trails are generally well-marked. If you visit, you have to cross over into the Michael Ciaiola Conservation Area on the New York side and see the lovely waterfall. When I was there it was flowing to the point where I could not cross to the other side, so I had to retrace my steps back on the Orange Trail. Probably my favorite local falls because they are not overrun with people.

hiking
Wednesday, July 11, 2018

Wider then average and better maintained then average trails make it easier to minimize exposure to ticks and poison ivy. Curvy and hilly but not steep. A pleasant walk that’s not to long or to short. My dog and I enjoyed it and will be back.

Sunday, June 17, 2018

6/2018 Great hike be aware lotsa trees Dow due to recent tornado you’ll have to go over,under and around some but was nice and I saw no one else after look out rock

Sunday, June 17, 2018

Be aware some trees down across trail due to recent tornado. Still passable just a heads up

Sunday, April 29, 2018

Hardly a "hard" hike. Definitely more "easy to moderate". We parked in lower lot (upper lot was closed) and actually hiked the white Trail which ran parallel to the pond, intersecting with the red trail (basically a fire road) and then back to the upper lot. Lots of trees down and very muddy after all the rain we had but, nonetheless, a beautiful trail filled with lots of little waterfalls and views of the pond. Clocked this trail at 5.2 miles not 3.3 but we did sort of make our own way around. Wear bug spray and long clothes - this place is infested with ticks.

Thursday, April 19, 2018

loved it, scenic moderate hike, nice workout going back up the mountain!

hiking
Tuesday, February 27, 2018

hiking
Friday, February 23, 2018

trails not marked well

hiking
Sunday, February 18, 2018

I live 5 minutes away and I absolutely love this place!! Many different options for a hike...trails link up with Michael Ciola Conservation Area as well. Well maintained trails..blazed really well and also numerous spots to sit and enjoy lunch. I will be back for sure!!

hiking
Sunday, February 18, 2018

Great hike, easy

Tuesday, January 23, 2018

Great spot! Check the additional “hardscrabble trail” loop off the purple and white trails.

Saturday, September 30, 2017

Awesome hike!

hiking
Saturday, September 02, 2017

The main trail appears to be a fire road (?) that climbs/traverse the ridge on the W. side of Squantz Pond. Its smooth going for the most part with a few sustained climbs.descents that must contribute to the "hard" difficulty rating. There are some interesting large boulder formations and rock faces along the trail and a great view of the pond from the meadow at the South end. I enjoyed it on a nice day.

hiking
Saturday, June 03, 2017

Good place to get some serious exercise with the trails going up and down the mountain.

hiking
Tuesday, May 23, 2017

My favorite spot

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