Fairfield, CT Snowmobiling Trails and Maps

1498 Reviews

Looking for the best Snowmobiling trails around Fairfield?

Find the top rated snowmobiling trails in Fairfield, whether you're looking for an easy short snowmobiling trail or a long snowmobiling trail, you'll find what you're looking for. Click on a snowmobiling trail below to find trail descriptions, trail maps, photos, and reviews.

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Recent Trail Reviews

Maybrook Trailway

5 Star

July, 2024 by z4g9gshqpr

The smoothest trail you will find anywhere around NYC. Nice and long, mostly flat. As others have pointed out, plants are beginning to overgrow on the Dutchess County end and need to be cut back. But the trail goes by numerous lakes and offers fantastic views. Highly recommend. Just make sure to start early because the trail is quite long.

Maybrook Trailway

Maybrook to Brewster

July, 2024 by bktourer1

Excellent trail except for the staircase once you get into Brewster from the Danbury area. Why wasn't a ramp put in instead of 2 steep staircases to carry a bike up or down?

Maybrook Trailway

Incredible Trail -- Almost impassable in Dutchess County Right Now

July, 2024 by dryaun

The Dutchess County portion of this incredible biking trail is almost unusable right now. Weeds wildly overgrown and sticking out 4-5 feet into the trail on either side. The Dutchess County people responsible for this negligence should be ashamed of themselves.

Accordion

Heritage Trail (NY)

Heritage trail

July, 2024 by flywithme_tl

A great ride . A watch for when you’re in Goshen , if coming from Harriman when you get to where it says end of trail in Goshen proceed straight across into parking lot continue on railroad ave make left on west main then take west main until you see a cemetery on the left then make a right onto a paved walkway near the dead end street then make left to continue on the trail . I am writing this to help others poor signage

William R. Steinhaus Dutchess Rail Trail

great ride William trail

July, 2024 by flywithme_tl

Can’t say enough well maintained , a must do !

Norwalk River Valley Trail

Two Trails

July, 2024 by z4g9gshqpr

These are really 2 separate trails with a variety of surfaces and a bit of street riding. The Norwalk trail is mostly asphalt going north from the sound while the trail in Wilton has about half going through a wooded area with pea gravel. This is the most enjoyable spot to ride as the other half of the Wilton trail dies out north of town on Route 7 with nothing around. If they were ever able to connect the two routes you would have something.

Briarcliff-Peekskill Trailway

Briarcliff-Peekskill trail

July, 2024 by joseph.avdek

I entered the trail on Ryder Road in Ossining and ran to the Teatown preserve and back (approximately 6 miles).

The trail is overgrown and not well maintained. There are points that are severely sloped and there are rocks hidden in high grass. Along the trail there is a creak that has stagnant water. The high grass and water leads to a large amount of bugs. I found a tick on my leg after the run.

On the trail there are abrupt up-hills that are not maintained or easy to traverse without coming to a slow walk due to rocks and roots. The scenery is beautiful but the trail needs a lot of love and care.


Maybrook Trailway

beautiful trail with an ownership dispute

July, 2024 by vbergerg_tl

Beautiful needed trail, extending the Dutchess Trail down to Brewster. Pity there seems to be some big ownership/maintenance dispute going on I guess between Dutchess County and NYS? Because right now no one is cutting back the weeds on the Dutchess County side and there’s a big defensively toned sign up saying that Dutchess County is not responsible.

Sue Grossman Still River Greenway

B bear aware

July, 2024 by willthegreat

Twice this week I saw a bear x the trail near the USA transfer station.
Also saw two women digging up poppies! That's a no no!
The extended trail that ends by the motor vehicle bldg has beautiful poppies and other ornamentals! Well done you guys!

Farmington Canal Heritage Trail

love this trail

July, 2024 by pamiller919

The map shows a disconnect, but the trail went all the way through. We did the whole trail and although it had a bunch of twigs it was a great ride. Well marked and in very good condition

Ocean Parkway Coastal Greenway

Enjoyable Ride

June, 2024 by manselmo77

One of my favorite rides of LI. Good speeds/pace going east. Return headwind can be tough.

Ellen Farrant Memorial Bikeway

Easy Ride

June, 2024 by manselmo77

Flat, great breeze and plenty of sun. Beautiful views heading down to Jones Beach then connect to Ocean Pkwy. Easily put in 20-30 miles round trip.

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