Looking for the best trails around New Milford?

Explore the best rated trails in New Milford, CT. Whether you're looking for an easy walking trail or a bike trail like the Hudson River Brickyard Trail and Walkway Over The Hudson. With more than 73 trails covering 587 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.

Recent Trail Reviews

Southwick Rail Trail

please beware

March, 2023 by jillm56

It’s a beautiful trail. BUT, please beware of the yellow post they have installed at all the road crossings to keep motor vehicles off the trail. As I was crossing the road at one of the crossings, as I came back onto the trail my handlebar caught the post and sandwiched me in my bike and the bike and I went down hard. I ended up fracturing my back. So please be careful on this trail through Southwick.

Windsor Locks Canal State Park Trail

I do my run here a few times a month, It is so beautiful I really like it. It is so green and right next to the CT River the air is so clean. It's good for a long run where you can get up to 10 miles and it's a well maintained trail.

February, 2023 by yikertam

I do my run here a few times a month, It is so beautiful I really like it. It is so green and right next to the CT River the air is so clean. It's good for a long run where you can get up to 10 miles and it's a well maintained trail.

Charter Oak Greenway

Not the best place to ride after 6.5 miles.

January, 2023 by darkstar826

If you ride longboard or inline skate. Get ready for terrible ground. if you start from Bolton State Park.. After 6.5 miles of riding... The ground is so mess up. There is so many cracks on the ground. Just be careful. Beside that, this trails has best downhill and cool turns.

Accordion

Norwalk River Valley Trail

Great Trails

January, 2023 by asiamcraejohnson

I’ve completed the Wilton trails in Lovers Lane, Entrance near Orem’s Dinner and Mathews Park. All are great. My favorites are the Wilton Trails, you enter and your engulfed in nature. Absolutely beautiful. I also love walking In Mathews park although that is more of a city trail to me not as much nature as these are concrete paved and you pass near traffic and such. So grateful to all the hard work put into to providing these trails thank you!

Harlem Valley Rail Trail

Rod it in sections

December, 2022 by bblhed_tl

I rode this over two separate weekends, Once from the Wassaic train station to Millerton, and once from Millerton to almost the end of the trail. Picking a favorite section is a really hard call, they both have their pluses. One of the things I really liked is the lack of level crossings making this more of a bikers trail than a walking trail with a lot of trail where you will only see bikes for a few miles. Pedestrians are great, with only bikes there is a lot less stress about passing. I think just about every level crossing has a portalet, even the ones without parking.

Wassaic didn't offer much in the way of attractions or close by food, Millerton on the other hand had plenty to offer and explore, there is even an actual bathroom on the trail in Millerton. While it would probably be fine to bike the town, I used the rack and walked it. Lots of interesting shops and food options in Millerton so it is worth stopping. Once you head north of Millerton you are back in open land with the occasional road crossings. There is a section where you ride over a large pond on a bridge that is nice.

Railroad Ramble

Nice but not exactly a "bike" trail.

December, 2022 by bblhed_tl

Walked this trail on 10/22/2022 and while it is a nice bike able trail, there are a few problems. I noticed that a few of the bridges are a couple of inches higher than the trail surface, and I'm not saying a little bump, I'm saying stop and walk it or fall off your bike bumps. Other than that this was a really nice trail and I would bike it with caution, or a mountain bike. Fall colors were amazing while I was there.

Windsor River Trail

very nice and clean

November, 2022 by haseenarasool808

It’s beautiful good for kids nice and clean .

Wallkill Valley Rail Trail

Great summer ride

November, 2022 by senseibarb

We rented bikes in new paltz to go from there up past Rosendale trestle The rest was closed but that was ok. We past some interesting caves with cold air which was a nice surprise. It is finely crushed gravel which is an up grease from mud; however check your bike company to make sure your tires are appropriate for this type of gravel Definitely picturesque, quiet and peaceful Would highly recommend

North Shore Rail Trail

ok ride

November, 2022 by senseibarb

Yes the path is new, surrounded by greenery and tuck back from the main road. My biggest complaint is the amount of crossroads at the beginning in smith town. Too much interruptions AND You really need to be careful even when you hit the rider alert button for crosswalks The ride itself is nice, but no facilities on path.

Harlem Valley Rail Trail

Beautiful scenery along the route but some segments need maintenance

November, 2022 by earth2wayne

The Harlem Valley Trail from Taconic State Park to Wassaic (Metro North Station) spans 24 miles through beautiful farmland and marshy areas with Mountain ranges on both sides (Berkshire and Catskills). The entire trail is paved with asphalt. Unfortunately, there are older segments that sorely need maintenance, especially the roughly 4 mile stretch from Taconic State Park south. The trail is also narrow in spots making it uncomfortably close for bikes traveling in opposing directions. The trail does pass through several towns where you can find places to eat and shop.

Heritage Trail (NY)

Love it!

October, 2022 by danghung1402

Beautiful bike trail to enjoy the fall colors. Love it so much. Highly recommend.

Timp-Torne Trail

great hike!

October, 2022 by rozzy_rocks

This trail is well marked and is a great combination of climbing steep rocky sections and walking flat sections with decent views. For someone out of shape, this hike is a great workout with plenty of resting spots.

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