Explore the most popular trails near New Fairfield with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

New Fairfield, Connecticut Map

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.

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.

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.

on Squantz Pond Trail

3 months ago

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

3 months ago

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

4 months ago

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.

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

trails not marked well

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!!

7 months ago

Great hike, easy

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

Awesome hike!

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.

Saturday, June 03, 2017

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

Tuesday, May 23, 2017

My favorite spot

Monday, March 20, 2017

This was a hard hike due to the recent 20" snowfall so thank goodness for snowmobiles as they packed the snow down enough to make hiking possible. We didn't see another sole on the woods except for two snowmobiles on the way back. This would have been a great time to snowshoe through here. Was a gorgeous winter hike and pretty good exercise.

Sunday, January 22, 2017

I hiked it earlier today, 1/22/17. First time there and really enjoyed it. It was a nice little challenging loop up the hill. And then I really like the little loop down along the shore. And all the rock formations are sweet. And the Brooks are flowing nice and strong so I had the noise from the water rushing. All in all very nice day. Oh, I also saw a bunch of Redtail Hawks and two bald eagles. I'll be back when I gets warmer to drop my canoe in the water.

trail running
Saturday, November 26, 2016

Made same 3.3 mile loop as Sean recorded in August, following the forest road NW and curving south along lake shore, then yellow uphill to the nice overlook over Squantz Pond.
Road part is great for running. The ascent later is a steep hike, you are rewarded with the great view at the top.

trail running
Tuesday, October 04, 2016

Awesome, challenging, and few people (depending on where you go). I typically head to the east side of the pond, and then head north on the trail that follows right along the water--seems to be used by fishermen. The trail itself is not extremely challenging, but if you head farther east and up the mountain it gets STEEP!

Wednesday, September 07, 2016

Loved it

Saturday, March 05, 2016

Freezing cold!!

Tuesday, November 03, 2015

There are other patches of land off of the main section. They're on Short Woods and Beaver Bog. Parking for the main section is always free on Pine Hill Road plus it puts you at the top of the mountain. It cost around $6 to park at Squantz Pond.

Friday, August 21, 2015

My kids and I enjoyed a great afternoon lounging on the beach at squantz pond so we decided we needed some exercise before we called it a day. I thought we were going along the main trail but we ended up on very narrow and overgrown paths along the lake. It was gorgeous and fun to explore but this is not a trail for young kids. Next time I'll look harder for the main trail.

Tuesday, June 16, 2015

There are many trails available in this area. You can spend 30 mins doing a loop or go exploring and spend a good amount of the day in the woods. Nothing special unless you are making the trek to the lookout by Squantz Pond, then there is a spectacular view.

Tuesday, June 16, 2015

One of my favorite local trails. There is a trail that runs along the side of the pond, as well as one that is a but further up on the fire trail. Both of these trails eventually make it to the top of the mountain for a beautiful view of pond/lake and surrounding areas. On a clear day you can see quite far at the lookout.

Thursday, July 28, 2011

In addition to the earlier review, you can find Fool's Gold in the stream that comes down from the hill on the far side of the beaches. We used to come here all the time as kids. It can get kind of crowded on hot weekends in the summer with people coming from out of state to cool down.

on Squantz Pond Trail

Monday, July 04, 2011

This was one of the first hikes I took with my mom and mom's boyfriend when I first went to school @ wcsu. Decided it would be the perfect opportunity to explore the area. Its a bit confusing to find when you first go, but can find the times afterwards. Take the main trail up, which is somewhat hilly, grassy but offers nice scenic views of the surrounding areas in southwestern ct. Take a picture here! As you explore the park, you can take in nature and take pictures along the way. At the end of the hike, take a seat by the pond and just take a look over the water, take a break to eat a snack. Take a picture here; it is scenic. Overall, this park can be completed by anyone, is one of the cleanest ones I've been to. Take a peak for yourself; you won't be disappointed!

14 days ago

21 days ago

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