Only a Mile of Up

photoNo one was around this weekend, so I did the week’s long ride alone. Normally, we’ll go out for 40 to 80 miles with a stop or two for coffee. Sometimes we ride into New York, other times we’ll go as far as Massachusetts. Yesterday, I didn’t get more than about 5 miles from home as the crow flies. But I rode 43 miles with 5,000+ feet of climbing. There’s a hill between South Britain and the Housatonic. Its main peaks are called Flatt Hill (I want to kill the bastard who came up with that name) and Horse Hill, but really, it’s all part of one hulking lump of geography that rises 600 feet over the valleys of the Housatonic and Shepaug Rivers, and of Transylvania Brook (A small part of which I own). Collectively, the area is known as The Purchase.

There are 8 roads up The Purchase. I began with Flag Swamp Road off 172 near the Southbury Training School. It starts out paved and runs up through a few small developments. Soon, it rises through a hemlock glen, and then turns to dirt at the Roxbury line. Flag Swamp Brook runs to my left through the mixed hardwoods. Peaking at the intersection with Mallory and West Flag Swamp, I drop down Mallory to Garnet. At the far end of Garnet is an old garnet mine, but first come some of the steepest bits of the ride, between the banks of an old cut, on the road’s washed out dirt and gravel. Topping out on Perkins Road, I head over to Cassidy, which turns into West Flag Swamp as it enters Roxbury. If you didn’t know it’s a public road, you’d think it’s a private drive. One lane’s worth of loose gravel and potholes, it’s one of my favorite roads. I pass another cyclist on it, the only time this has happened in the dozen years I’ve been riding it. Then it’s down Mallory to South Street and onto West Purchase.

I detour onto Lower Falls Road for a glimpse of the Shepaug, then loop back onto West Purchase. In about a mile the first pitch on West Purchase hits me like a head butt. I don’t know how steep it is. I need the smallest of my three chainrings, one of the few paved sections on this ride where I’ll use it. It’s so steep that when I slide my ass back on the seat to climb, my front wheel lifts off the ground. It’s a constant balance between traction and control. At the first peak, I stop for a photo. Then it’s down and around a hairpin left and back up again. At the top, a driver who’s pulled over to make a phone call gives me a thumb up, and says, “That’s a hell of a hill.”

I turn left, make my way back to Brown Brook, and bomb down it at 45 mph. The wind pushes the sweat out of my helmet pads and it drips into my eyes. At the bottom, I swing around and climb back up what I’ve just descended. At the top, I empty my first water bottle. Spotting a man loading a kayak onto his car, I stop and ask to refill the bottle at his hose. I have another, but I’ll need at least this refill. He ascents, and we chat for a few moments. Thanks, Lou!

Now down Purchase Brook and up the two steep steps of West Flatt Hill to the summit by Peach Orchard. The land here is corn and hay fields with a few houses and little shade. I’m glad it’s clouded over. Here is my big payoff for the day, the windy, fast descent on Flatt Hill to the Audubon Center by the horse barns in South Britain. What’s fun going down must be fun coming up, so I reverse and sweat my way to the top. I stop at Peach Orchard to stretch out my back. A woman jogs by, and we say good morning. I continue on, riding down to the Housatonic on what is also my route to work. At the bottom I text Pat to let her know I’m good, and I watch the RC planes flying at Mitchell Farm for a few minutes. Behind the planes and below the Shepaug Dam are several massive satellite dishes, used I’m told, in communications with marine shipping.

Riding back up, I encounter the only asshole of the ride, the driver of a diesel Chevy pickup. He’s tailgating the car in front of him, and he passes me so close I feel the heat of the exhaust on my leg. It’s not personal though, because he then passed the car he was tailgating on a blind hill. One can only hope that he’s alone when Darwin comes calling.

It’s starting to hurt now, and I’m hungry. I’ve been taking bites from a protein bar every so often. Balancing between staying fueled and not puking, it’s enough to keep me from bonking but not enough to keep my stomach from growling. I climb the steep pitch at the top of Purchase Brook, and follow it around to the top by the Training School’s farm. Once state-of-the-art dairy barns are disused and overgrown. The hay fields are rented out to a local farmer, who I pass as he’s driving the other way on a Farmall with a sickle bar. You don’t see many sickle bars these days, but Farmalls are still ubiquitous here even though the company bankrupted 40 years ago. That’s a testament to quality. Circling the hill top and its old orchard, half a dozen wild turkey chicks flee into the weeds at my approach. I turn left down Spruce Brook, passing Stone’s farm, and reaching 49 mph on the steep, straight descent. Coming back up at one tenth of that speed, I’m passed by a milk truck with “Cabot’s” blazed across its back. Just below the top, I pass it backing into Stone’s.

One more hill, Constitution. I wind down it, through the Training School’s cottages to 172 about a quarter mile from where I began on Flag Swamp. The Connecticut Challenge Century is passing, and I chat with a few riders who comment on the hills. Yeah, we have them here. I clip in and head up Constitution, which I’ve saved for last because it’s the easiest. I think it was laid out in the 1930s when the Training School was built. At least, engineers seem to have had a part in its switchbacked design and relatively easy grades. I’m pretty sure the other roads were laid out by 18th century farmers looking to maximize land use, and mainly unconcerned with transportation. The grade on Constitution’s final pitch is so shallow that my tired legs spin up it at 18 mph.

Finally, I bounce down the dirt of West Flag Swamp and Flag Swamp all the way to South Street. Two small hills lie between me and home. I use my little chainring on both.


About swampyankeecyclist

I'm Andy Engel, just a middle-aged, middle-class guy from Roxbury, Connecticut. I've been married to my best friend since 1988, and we have two grown sons. I like riding bikes, and my biggest accomplishment is the 180K D2R2. I own 5 bikes but my go-to rides are a 2016 GT Grade gravel and commuter bike and a 2016 Specialized 650b hardtail mountain bike. Additionally, I have a 2000-something carbon-fiber Orbea road bike, a 1990-something Specialized Sirrus that's my old dirt and commuter bike and which now serves as a spare and a trainer bike, and a 1985 Ross Mount Hood MTB. All but the 650b have Brooks saddles. I work from home now, but used to commute 32 miles round trip to work by bike year round. I was a carpenter and still love building things, but regular paychecks, insurance, and vacation time lured me into journalism. I've written a couple of books on carpentry, and I've been an editor at Fine Homebuilding, Fine Woodworking, and Professional Deck Builder magazines. Currently, I manage construction events at the JLC Live and Remodeling Show trade shows. Additionally, my wife and I run Transylvania Guest House, an Airbnb. Find us on Instagram. Come stay with us and I'll show you some great cycling.
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5 Responses to Only a Mile of Up

  1. Tim Schreiner says:

    Andy, before we met and started cycling together, I lived on Stilton Road on the top of The Purchase — and from the blog list, the only road on that hill you didn’t ride. It’s only a half- mile long and connects Purchase Brook with Swamp Brook neat the old School orchard. I love/hate those hills on a bike. They’re so hard that one snowy night I couldn’t make it up either hill in my pickup.

    • You’re right – I didn’t ride Stillson. I only came up from the Hous side once, and it was a choice between Stillson and the upper pitch on Purchase Brook. I’ve ridden it many other times though. It’s a good one. Planning to go out for hill repeats this evening. D2R2 is in less than a month.

  2. Tim Schreiner says:

    I meant Spruce Brook, not Swamp Brook. It’s been a while

  3. Paul DeGroot says:

    Another well written piece! I love your “when Darwin comes calling” !

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