March 14, 2020, seemed like a normal Saturday ride for our group of gravel enthusiasts (the “Dirty Bird Crew”). Our route guru Brian had put together another fantastic route, exploring dirt roads and trails a short drive from New York City. Every weekend, year-round, we are out exploring the (surprisingly!) high-quality dirt roads and trails in the greater NYC area. We’ve gone out in nearly every weather condition, from swimming holes in the summer, to snow rides in the winter, and even riding across frozen lakes with studded tires when it’s bitterly cold, but nothing had prepared us for the months ahead. Drinking post-rode beers there was some talk about Covid-19 and the possibility that we may be working from home for a few days. We said our goodbyes until next weekend, but little did we know this would be our last group ride for months.

Fast forward a few months, and despite NYC flattening the curve, the summer solstice had come and gone, as fleeting as the dreams of a “Big” bikepacking trip. Many of us were forced to cancel highly anticipated bikepacking trips to the American West and European mountains. Between the endless stream of Zoom meetings, workdays seemingly never-ending, and days bleeding into weeks into months, the quarantine blues were hitting me pretty hard, especially without any adventures to look forward to. The irony of quarantine and self-isolation is that now, more than ever, our connection to nature is critical to both physical and mental health. Anyone who has ever ridden an overnighter knows that it is not the same as a full-week, full-on adventure, but it is certainly better than nothing. What better antidote post-lockdown than a local overnight adventure!

We have a wide library of routes at our disposal and since the quarantine had limited our chances to get out and ride our summer “classics”, the options seemed endless. We quickly settled on Litchfield County, CT as the focal point. Situated in the northwest corner of the state, there is an abundance of gorgeous dirt roads, trails, and other “weird” bits. One of the highlights of Litchfield riding is “The Tunnel” – a remnant of the defunct Shepaug, Litchfield and Northern Railroad – now permanently preserved by the Steep Rock Association . The tunnel was constructed from 1871-1872 for the railroad, whose original function was to transport fresh milk and cheese to New York City. Nearby, another perennial favorite is Macedonia Brook Road, a glorious dirt road next to its name-sake brook – it also happened to host a state campground that had recently reopened. Using these two landmarks, Brian and I crafted a route that took in as many of the dirt roads and trails. We wanted a route that would be fun to both experienced bikepackers, but also approachable to first-timers, as our group was about a 50/50 split.

Despite the many (many!) emails about bikepacking kit, bags, packing strategies, etc, the real reckoning came in the train station parking lot. The excitement was palpable as rigs were assembled and everyone could checkout setups in person. Final adjustments made, straps tightened, dangles dangling, we – Akiko, Bonnie, Brian, John, Kevin, Paul, Tom, and myself – clipped in and started our adventure. Douwe, who was only joining for a day ride, looked bemused as we got accustomed to the extra weight and settled into a bikepacking pace. After a brief transit stage, we’re soon riding parallel to the Housatonic River on a wonderful dirt road. After traversing along the riverfront for a few miles, we turned up Rooster Tail Hollow Road on a steep kicker that quickly reminded everyone of the additional weight that we were carrying! We were rewarded with bucolic farmland views as we gradually traversed deeper into Litchfield County. Cresting the top of a rise, we turned onto Walker Brook Road, a can’t-miss road on the way to the Tunnel. Six miles of dirt descending alongside a babbling brook is the definition of pure, unadulterated gravel bliss. At the bottom of the descent, we crossed the Shepaug River, before climbing the painfully-steep Battleswamp Road. This was a totally gratuitous loop, but we could not resist the siren song of chunky singletrack fun.

Back at the Shepaug, we began a gradual climb up to the old railbed on the approach to the Tunnel. At only 293 feet long, its length belies its mystery and allure. The curved cut through the sheer rockface creates the illusion of an endless abyss. After the obligatory photo-op, we continued through the Steep Rock Preserve to Washington where we had a stream-side picnic. After lunch, we continued to follow the Shepaug before crossing it to enter the Hidden Valley Preserve. Here, we would again rejoin the railbed, tracing its sinuous route alongside the Shepaug. The railroad was famous for its circuitous path: 32 miles of rail to travel 18 miles as the crow flies, once described as “the crookedest railroad east of California”. Following the serpentine flow of the Shepaug, we could see the origins of its name – In the Mohegan language, Shepaug translates to “rocky river”. The water flowing over rocky terrain, littered with boulders and Herons are a picturesque example of quintessential Litchfield County.

After exiting the doubletrack, we traversed quiet country lanes, following the undulating topography past endless tapestries of green and countless ancient stone walls. The heat and humidity were becoming oppressive, but fortunately, we were able to spot a small swimming hole in a nearby brook for an afternoon cooldown! Newly refreshed and rejuvenated we made our way to the town of Kent where we picked up food for dinner and other sundries. It was about 5 miles of gradual climbing to the campsite and loaded down with miscellaneous bags and backpacks full of supplies we must have looked like a motley crew! Arriving at camp we quickly set up tents and collected firewood for cooking. Everyone one had carried some shared supplies and we were treated to great fire-roasted food: local corn on the cob, sweet potatoes, asparagus, paired with hot dogs and sausages – my most gourmet bikepacking meal to date!

Leaving camp in the morning, we continued on rolling dirt terrain, past more stone walls, and horse estates. After a short, rowdy descent, we turned onto Bog Meadow Road, an old woods road that traverses through eponymous terrain, skirting streams and ponds, passing abandoned structures and our favorite rusted-out car. The recent hot, dry weather had left the trail in hero conditions, making it the most rideable and fun trip down this memorable section. We’ve been on this “road” several times over the years, but never during the morning. The dappled light filtering through the tree canopy was an incredible experience, only made possible by camping nearby. We had one final stop at the Sharon Audobon Raptor Aviaries, housing ravens, owls, falcons, and, most memorably a bald eagle.

After a requisite stop to see donkeys and a very large pig, we hopped on the Harlem Valley Rail Trail, another repurposed industrial remnant. Leaving the flat trail behind, we started another gradual dirt climb, Deep Hollow Road. After a brief detour to the mostly intact iron furnaces, we entered Millbrook, where we saw more horseback riders than cars. We climbed up to the Taconic Hereford 909 MTB trails for some more singletrack. This was a new area for all of us except Brian, and boy, it was a treat! Up and down, the trail alternated between flowy singletrack and chunky, root-littered sections before a rowdy descent dumped us into a ravine with no visible track in sight. After much map consultation, we decided the best way back to the route was to hike-a-bike up the ravine to a connection to a trail Eventually, we were back on route and were treated to a fast, fun woods road descent before reentering civilization. The outdoor roadside BBQ joint we found was a perfect treat after this tough section. We were on the home stretch now, and again the mercury was creeping up towards 100°, so we decided to take a small detour in search of a swimming hole. This meant missing out on some dirt, but also some climbing, a trade-off we were happy to make. As we followed the Ten Mile River, we had our eyes peeled, but many of the promising spots were restricted by private property signs. Just as we were about to give up, we spotted some locals hauling a cooler down to the river and we knew we struck swimming gold!

While it wasn’t the same as a “Big” Trip, our overnighter was just as impactful; a poignant reminder of the restorative power of bikes and bikepacking. It allowed us to string together many of our favorite segments, ride further afield, and see familiar scenery in a new light, literally. We had a more intimate experience with the scenery, the history, and the mystery of our local riding area. And I’m happy to report that everyone, especially the first-timers had such a great time that we couldn’t stop talking about the next trip!

Photos:
Akiko Ando-Gigliotti @akgigliotti
Bonnie Osborn @bonniecharm
Brian Sullivan @iambpsully
John Siemens @siemensja
Kevin Graney @kevgraney
Paul Crowell @cropau62
Tom Buchok [no Instagram]