This is what I knew about the Ives Trail before I decided to hike it; it begins in Redding and ends in Ridgefield, or just as reasonably the other way about; it is 20 miles long roughly, and hard going in places; it is named for Danbury-born composer Charles Ives (1874-1954), which presumably explains the trail’s distinctive G-clef blazes. And that was basically it. Before I set out, I printed and laminated the Overview Map from the trail’s website. The map showed how the trail snakes through the least developed land of Danbury, squeezed between the city to the north, and the residential lanes of Redding and Ridgefield to the south. Finally, I mailed an acquaintance who has been associated with the Ives Trail forever. Mike replied with tips that boiled down to: blazing might be erratic, there are steep climbs, watch out when crossing Route 7.     

I chose to hike in the Redding-Ridgefield direction. It offered better options for my wife to pick me up when I was finished. I was not at all sure that I would manage the full 20 miles, but felt confident of at least reaching Route 7 at Starrs Plain Road. If I did do the whole thing, Charissa could meet me at Bennett’s Pond State Park, a place we knew. This seemed much better than calling her from some unknown spot deep in Danbury or Redding. We are not GPS-enabled. Apart from miles, terrain, and an aging body, another cause of doubt about finishing the hike was the forecast of afternoon thunderstorms. Since the afternoon would see me on top of Wooster and Pine Mountains, I would bail if the skies began to rumble.

I left home soon after sunrise; but there was no orange glow, just gray sky and thick, motionless air. I parked opposite West Redding Post Office, sprayed my cap and shirt with Off!, and set out along Sidecut Road. Warning! The Ives Trail begins inconspicuously, a small hole in the roadside brush. You could walk right past it, as I did. And the first half-mile – called locally the Sidecut Trail – is a tight path, overgrown here and there. It ends at the railroad tracks, which you must cross to reach lily-choked Bogus Swamp and the onward trail. Then you climb into the woods and a corner of Bethel, and do not emerge into the full light of day again for over an hour, by which time you are well into Danbury. Despite Mike’s warning, I missed a couple of twists of the trail on this section and had to double back to pick it up again. Simultaneous with one of these lapses, I smelled frying bacon and was reminded that it was time for breakfast and that I was not as far from people’s homes as the thick woods suggested.

The half-mile of Ives Trail that uses Long Ridge Road was pleasant relief from timber and solitude. I emerged first at a well-lit clearing brightened further by mauve wildflowers, and then at the road where I met a gardener and dog-walkers. Next it was back to the woods. Even now, just two weeks later and with the aid of maps, it is difficult to stitch my memories of the two-hour hike to Parks Pond in Tarrywile Park into sequence, or to match them to identifiable places. I know I had to follow the trail blazes diligently, now often painted yellow diamonds because people had made off with the plastic g-clef variety. The blazes led me through woods of middling beauty, out to a broad track, and eventually to a steep ascent. There had been a few other climbs worth the name this morning, but this one left me hot and tired at the top of a nameless hill, feeding myself dried apricots in the hope of energy. Soon Tarrywile Park was announced by a shelter and information board. There was no information on the information board; a pity, because the Ives Trail is only intermittently blazed in the park and it would have been reassuring to know that all I had to do was follow the blue- and white-blazed trails to the dam at Parks Pond. As it was, I muddled my way there, filtering water from the pond’s feeder stream to top up my depleted supply.        

The Ives Trail between Parks Pond and Route 7 is ordeals and rewards. The ordeals are the sharp ups and downs – up and down to Back Pond; up, up, up to Mootry Peak; down into a rocky canyon; up and over Moses Mountain. The rewards are tall, straight trees; the view of Danbury from Mootry Peak lookout; the cool air of the canyon; and, on this day, a downpour splattering Sugar Hollow Pond, a body of water I had only glimpsed before from Route 7 at 50 mph. The downpour did not last, and it was unaccompanied by thunder, so I crossed Route 7 to the last leg of the trail. (Mike had warned that pedestrians have about 7 seconds to cross the highway after pushing the button, and even so not all drivers deign to stop for the red light. My crossing was trouble-free, but it could be different at 5 p.m. on a weekday.) The woods on Wooster and Pine mountains had more than middling beauty, sprouting often from a lush bed of fresh ferns. When the trees broke fleetingly at Pine Mountain overlook, the view had changed dramatically since my last visit six weeks before – a dense green covering the hills now, the gray-brown of trunks painted over. I called my wife here to say I would finish by 3 p.m., and pushed hard over the remaining distance to make sure I did. Five minutes from the finish line, clouds began to swirl and rumble in the west, and I pushed harder still.

Likely it was all this pushing that gave me a souvenir of the Ives Trail – a sore and stiff knee that lasted for two full weeks. But I liked the trail, and will return to it, although probably not to all of it in one day.    

Rob McWilliams is a local resident. Taking a Hike appears monthly. Contact Rob at “McWilliams Takes a Hike”, blog and Facebook. He’d love to hear from you.

If you go …


REDDING END - Opposite West Redding Post Office. RIDGEFIELD END - Bennett’s Pond SP, Bennetts Farm Rd.


About 20 mi.


9 hours.


Maps available at Best to take all four available maps on your hike.


Long pants; bug spray; trekking poles; lots of water or a water filter; plenty of food and snacks.