Explore the best rated trails in Plainfield, CT, whether you're looking for an easy walking trail or a bike trail like the Southern New England Trunkline Trail and Windsor River Trail . With more than 55 trails covering 444 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.
What a perfect ride on a Monday afternoon. Delighted to stop at Plant City for refreshments before we turned around and headed back to Bristol.
Trail is nicely shaded, paved and fun scenery. Yes, 6 mile round trip is indeed quite short for us - and hence the rating of 4. We combined this with the Blackstone River Greenway (20 mile R/T), one of our favorites. Around a 30 minute car drive between the two. This trail does have rest facilities about half way at a public park. The Blackstone has none.
Beginning perhaps 2 miles north of the Simsbury Airport and continuing north for at least a few miles the trail will be closed for construction (looks like repaving + ?). I was on this trail yesterday and the "Will Be Closed" signs are abundant.
I rode 20.5 miles of the southern section of the Air Line Trail from East Hampton to Willimantic on a very hot day in June. This section of the Air Line Trail offers gorgeous scenery, peaceful seclusion and a tightly packed gravel surface that is in very good condition throughout. Despite the heat the trail is very shaded which provided much needed relief from the sun. There are a fair amount of road crossings, most are very small, quiet roads and all of the busier roads have warning lights that can be activated to let motorists know you are crossing.
The only two small complaints I have is there is a lack of signage along the trail. There is one very short on road section that I almost missed getting back on the trail due to there being no signage, I just rightly assumed the small unmarked path on the road was the way to get back on the trail. The gates at the road crossings are on the narrow side which can make navigating through the road crossings difficult. I feel these two issues do not at all detract from what this section of the Air Line Trail has to offer.
I just rode the trail from Cheshire to New Haven Harbor. It gets confusing because of the lack of signage once you go under the Temple St Garage in New Haven. You get dumped out into a street and don't know where to go. The trail is on the road or sidewalk depending on what you prefer. Take a left onto Grove St. continue to the end and take a right onto Olive ST. Follow Olive St. to the end and pick up the trail again on Water St. Cross Brewery ST and take a right to continue on Brewery. Brewery changes to Sargent Drive. Take a left to go under I95 and the water will be in front of you. If you take a right and continue down for a little, along the water's edge, you will find dozens of food trucks to buy lunch before a return trip. It was well worth the trip.
Great local path. It is all paved except for a short area near the Norton line. It has gravel for about 50 feet. Flat with lots of trees. Some finishing touches needed at the crossing but they have lights set up for safety. It’s about 13 round trip. Used by walkers, runners, bikers. Great place to teach kids how to ride a bike. Not too crowded.
We just got back from doing this trail yesterday.
We started at the north end at the Fort Hill Parking area.
There were plenty of spots to park when we arrived.
Being a very nice day, there were LOTS of people out enjoying the trail.
We only went as far as Police Cove Park where the trail was closed.
There was a detour route that continued but we decided that was enough for the day and headed back.
We did take the side trail out to the carousel, which we knew would be closed from checking on the web.
We were a little surprised that a trail so nice didn't have ANY restroom facilities. It wasn't easy to go into the woods between lots of poison ivy and people on the trail.
We'll go back and go from south to north and enjoy the rest of the trail
Just rode this trail today 5/27/25. My previous 5* review (2024) still stands with two additional comments. 1. There are virtually no port-a-potties on the trail. However, right near the southern end in Bristol there are some nice benches and just across Thames St is a very nice town facility. 2. The north end parking (India Point) is very busy and biking the first mile getting to the East Bay Path is involved with some unpleasant street portions. Use GPS to locate the parking at 66 Veterans Memorial Pkwy, East Providence. A much better option - in my opinion.
I recently rode this on a cool day in May from Manchester to Willimantic and back, so right at 40 miles. The trail is well-maintained and foot/bike traffic was light, even though it was a holiday weekend. Very scenic for long stretches and low elevation gain. I rode a gravel bike with 45 mm tires. On a road bike with reasonable tires, this should be do-able (I saw a couple of them), but there is one rough section of about 100ft (30m) where you would need to walk. There is also one underpass that is dark enough to use a headlight...but it's passable if you slow down. There are a number of places to read about the history of the rail line, as well as a few locations with fix-it stations with bike tools and air pumps.
One final tip: Google maps takes you to an intersection on Colonial Road for the Manchester trailhead...the parking lot has a tiny sign that is easy to miss.
...we rode the western part... (is there a tool to edit a review?)
We rode the eastern part of the trail today, starting at the CT/MA border towards Douglas. The first 6-8 mls are well maintained and a good ride even with a street bike. Nice scenery, too. But then things get worse around Douglas. Rough surface with crushed stone, sand and deep puddles after a rainfall (like today). Looks like the track has not been maintained in a while and detoriates. A mountain bike is a big plus and highly recommended in some parts of the trail. Was a good ride though but do not expect a smooth one.
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