Looking for the best trails around Woodbridge?

Explore the best rated trails in Woodbridge, CT. Whether you're looking for an easy walking trail or a bike trail like the Windsor River Trail and Niantic Bay Boardwalk. With more than 59 trails covering 498 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

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.

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.

Accordion

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.

Niantic Bay Boardwalk

always a beautiful walk

November, 2022 by christinemoretti

Bring a hat for windy days . Beautiful walk . Access to McCook park is up the hill if you want a longer walk.

Windsor River Trail

very nice and clean

November, 2022 by haseenarasool808

It’s beautiful good for kids nice and clean .

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.

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.

North County Trailway

beautiful & well kept trail!

October, 2022 by 9kw466jjyr

This trail is great despite the middle aged men speeding past you at 90 mph on their LeMonds. I’m not sure if they are bike messengers or just “has beens” trying to live out their dreams of being in the Tour De France, but their speed and shrill shouts of “Left, Left, Left!” piercing the crisp fall air can really ruin what is otherwise a beautiful and relaxing family outing.

Farmington River Trail

very pretty

October, 2022 by lpusztai

We biked from Simsbury to Farmington on the Canal trail. It was nice with the fall color, but there is not much else to see. On the way back we took the River trail. It goes parallel to the river and it is very pretty. It goes thru Canton, which is a charming little town. From there the bike trail is quite good for a while, but then you have to bike on the road. The bike trail sign is painted on the road, but you have to look for it. Traffic was not bad at all. The last part goes thru a simsbury park, there are a lot of roots, gotta be careful. All in all the river trail is very nice, even with a couple of miles of in road biking. there there

Hop River State Park Trail

Wonderful!

October, 2022 by kate.decena

Beautiful for a bike ride in the fall. The trail is well kept, the views are beautiful and is moderately trafficked. I started at the Manchester trailhead and just kept going straight, passing parking lots in Vernon and Bolton. Didn’t notice much options for restrooms or pit stops for food so plan accordingly.

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