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




















Rode October 2026, easy access off 84, beautiful Fall day, scenery is varied, paved surface was flawless.
So I started this trail in Portland, Connecticut, and about 3 to 4 miles into it. It stops at a marsh river area. There is no sign to tell you that it does or what detour to take. You would have to get on the main road to avoid this section. And the way people drive on that road I wouldn’t trust it. From what I heard, they were supposed to build a bridge over this section but said they were waiting for EPA to be involved which was years ago so I would highly recommend that you start in East Hampton for continued access.
Rode Pawley Trailhead to Hopewell Junction and back. Perfect, smooth, clear, pavement. No downed trees . Few easy road crossings, shady throughout. Nice lunch at Daddy Os in Hopewell Junction.
We did this trail in two days. We learned that it is not quite complete from Hillsdale to Wassaic. Trail is closed from Black Grocery Road to Orphan Farm Road about 1.5 miles. So be warned that as of Sept 15 you can’t quite go completely through YET. Above Millerton and below are almost two completely different trails so we were happy to be able to stop and explore at our leisure. Above is really farm and marsh lands while below has more towns and historical things to see and do. Millerton, has many places to eat and a great mid stop. The leaves are not turning yet but will be beautiful in the colorful fall. I heartily recommend the ride.
We rode from the parking lot at Quidnick St. in West Warwick to the abrupt end of the trail in Summit (Coventry), about 20 mi round trip. Pavement in very good shape. Trail is shaded for much of the way making for a pleasant ride. Lots of views of ponds, lakes, reservoirs and streams. Significant uphill climb to the end of the trail in Coventry but a screaming downhill for much of the way back. We plan to return in the fall, foliage will doubtless be stunning. Trail is paved throughout, and the western part of the trail is shared with equestrians, although sadly we did not see any.
This rider was going Northeast from Willimantic towards Hampton NOT Southwest from Willimantic to East Hampton. Having ridden both stretches I can say his description is completely wrong about the gorgeous and open riding Southeastern route and not completely wrong but somewhat overly harsh about his route which can get iffy for stretches.
Rode entire trail roundtrip on a sunny August day. It's a great trail with a great paved surface. Scenic, too. The southern trailhead (Wassaic) has a direct train connection to New York City, so it's just a matter of time before it's discovered by folks from the city for a day's ride.
Town of Millerton in center of trail had the best facilities for a mid-ride break. Copake Iron Works Museum at Taconic State Park and close to the trail also well worth a visit.
Hubby & I went this morning for a trial run with my new e-bike! It was tons of fun!!!!
We rode this trail yesterday from the parking lot at Dunkin' Donuts in Moosup all the way to the Rhode Island border. The surface alternates between paved and stone dust/fine gravel and is very well maintained throughout. You can see where dirt bikes would have access coming through the trees down some of the steep banks but we did not see any, unlike the situation that other reviews have mentioned. Perhaps reinforcing an unfortunate state stereotype, immediately upon crossing over into Rhode Island where it is then called The Trestle Trail, after about 6 miles, the trail deteriorates significantly into a dirt trail and likely would be fairly muddy when wet with lots of deep puddles. I also noticed an immediate onslaught of bugs which was interesting. We turned around at this point as we only wanted to ride the Connecticut portion. I was very curious after reading all the reviews over the years about how bad this trail used to be. If you're looking for solitude this is your trail, as opposed to many of the Connecticut trails to the West. We maybe saw five or six people for our entire ride. The guy who owns the house in the quarry is super friendly, as is his German Shepherd Fiona, and offered us water since the day was fairly hot after seeing us from his porch. I highly recommend this trail if you're looking for a quiet, shorter 12-mile round trip ride. Only downside: zero porta potties along the route. You can hit the Dunkin' Do restroom before and after the ride.
Beautiful 1st ride on the Norwottuck Rail Trail. We parked at the Marshalls in Hadley (trail starts right behind the building) and road a little over 10 miles into EastHampton and back. It was a very easy ride (my 1st ride of this length) on asphalt.
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