Find the top rated horseback riding trails in Northampton, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.
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We rode from Pittsfield to Adams and back. Very nice trail. 50% shaded. Ate lunch at AJ‘s at Adams. Nice restaurant in an old train depot. Limited parking at the beginning in Pittsfield. Start your ride at the next parking area to the north. Lots of lakes and rivers running next to the trail. Asphalt the entire length of the trail.
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.
We hoped to do the entire trail by parking in the middle just south of Keene. The signage going through town was minimal and included being on the road quite a bit. The south side noted “road closed” because it’s being paved, but the road dead ended after 2 miles.
Disappointed is an understatement.
We rode the whole trail. It's smooth, scenic, and frequently bathrooms. The leaves are turning, such a beautiful trail. A must ride. It should be a Hall of Fame trail.
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.
A few too many crossings at the Leominster end, but its a fine trail. Last quarter mile or so on the Fitchburg end isnt so much a trail as it is street riding.
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.
Biked end to end on a beautiful summer day. An absolutely beautiful paved trail with lots of water features to see - lakes to the south, river further north, and views of the mountains. Nice trailside pub in Adams and other eateries, including ice cream. Well-loved, with lots of walkers and skaters, as well as riders. Benches and picnic tables aplenty. One of the best trails I've had the privilege to ride. The only way it could possibly be better is if it was longer.
Correction to someone else's review: trail goes gently downhill south to north (not north to south) from Cheshire to Adams.
If you are a dedicated mountain biker than this would be a 5 star. Don't do this trail if you don't have a mountain bike or those fat tires. I was on a mountain bike, and my son had a regular bike. The beginning of the trail is easy and lovely. Once you connect with the trail (beautiful water views) the trail becomes mostly rock with some sand. Passed 1.8 miles the trail is impassable with our bikes. Somehow we made it out and back without falls or bike damage. I have biked other ski trails that were more compacted sand and dirt with some rock. This is not that kind of trail.
Hubby & I went this morning for a trial run with my new e-bike! It was tons of fun!!!!
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