Char and I had been registered to ride two-up in the How the West Was Won (In the East) rally this year. After a few years’ hiatus due to pandemic and other reasons, we and many other east coast riders were really looking forward to seeing what Rallymaster Justin had planned for us and were happy to see another “new” event scheduled for the northeast region. HW3 was scheduled to take the Memorial Day weekend slot traditionally held by the Mason-Dixon 2020 rally for the past 20 years, and there was something comforting about keeping that holiday weekend booked for some fun rally riding. We were very much looking forward to riding our first two-up rally since the final Void.

Unfortunately, HW3 was again cancelled in late February, so we decided to just keep the long weekend PTO reserved at our jobs and plan out a riding getaway of our own. High on the list was the Dutchess County area of New York state, which lies between the Hudson River and Connecticut state line. It’s a mostly rural region with lots of farming and great topography for riding due to the the rippling elevation changes from the Hudson Valley up and over the Taconic Mountain Range and into the Housatonic River valley in Connecticut. New England Riders has a full week’s worth of day-rides in this region ready to load up on a GPS and just follow for some riding bliss.

As April waned, we needed to start firming up our plans. The NER trip agenda is based out of Fishkill, but the chain hotel rates there are always a bit expensive for the class of lodging, and they were completely unreasonable during this post-COVID holiday weekend. So I spent quite a bit of time on AirBnB looking around the region. Finally, I secured us a place for four nights on the outskirts of Poughkeepsie, the county seat and a former capital of the state. Neither of us knew much about the city or the area, but asking around gave us a bit more confidence in our choice. Poughkeepsie probably isn’t high on most people’s list of vacation destinations, but it’s well-placed for all of the great riding in the area, and has options for dining and some historical attractions.

I’d already booked a tire change with Break’r Bikes for the morning of the 23rd, prior to heading out on my BBG 3000 ride. I wanted to have reliable rubber on the bike for several days of two-up riding, followed soon after by the fast-approaching Iron Butt Rally. The Tripletred tire didn’t look too bad for its 45K estimated miles (bought used) – I probably could’ve kept using it for another few thousand miles of local riding if we weren’t heading off two-up. I threw the rear wheel and tire into the car and headed up to New Hampshire early that weekday morning to beat traffic. I planned to work from a coffee shop while I waited for my 9 AM tire appointment nearby.

Me & Ollie’s Bakery & Cafe is a great spot on Main Street in Exeter NH. A clean and roomy coffee shop with plenty of seating and free wifi, though I had quite a bit of trouble getting on the Internet there and ended up not getting a lot of work done. Definitely a nice place to stop off during a ride, though parking could be an issue for a group during busier times.

Keely from Break’r got my tire swapped out without issues, not even having to resort to the heavy hitter “basement machine” that is often required for mounting these stiff Tripletreds. They are such a great little shop, and I left behind a few pastries from the bakery as an extra thanks. Always feed your mechanics!

In the process of reinstalling my rear wheel and refastening the muffler bolts, one of the muffler clamps broke off after barely any tightening of the bolts. Ruht roh. Well luckily, not 6 feet away in my garage is another ST with a fairly shiny set of muffler clamps, which I borrowed  to get everything buttoned back up. After cleaning up, I immediately got online and ordered replacement clamps (and several other parts like muffler gaskets that had long since rotted away). I’d just use the new parts on the newer bike once I got back to working on it.

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Southeast MA – Poughkeepsie NY
May 25, 2023
(~193 miles)

After working a full eight hours on Thursday, we were both able to sign off early and get on the road by 16:15. The weather was perfect, around 68F and sunny, as we cruised in light traffic down I-295 into Rhode Island and picked up US 6 for a leisurely spin out into Connecticut. To get to the river crossing in Middletown, the GPS took us down I-395 and up CT 2, which turned out to be a pretty quick and efficient routing choice that I hadn’t tried before since I’m usually toodling on the back roads.

We crossed the Middletown bridge around 18:30, still plenty of light out from the evening sun. The town had that sleepy post-rush hour weeknight feel, with local folks out and about running errands or grabbing a meal. I’d earmarked two possible dinner spots in town, which is about our halfway point.

We ended up hitting the local pizza joint called Mondo, which has great reviews. The restaurant is in a boringly modern looking building down at the quieter south end of Main Street. They had a few tables on the sidewalk and the temperatures were still very comfortable and traffic quiet, so we decided to dine out in the evening air.

The eggplant fries were amazing and the New York style pizza we shared was delicious with fresh vegetable toppings and a crisp crust…really hit the spot. We needed to be at our AirBnB before 22:00 per check-in rules, but I’d allotted time for this stop, so we relaxed into our food a bit. Let our minds start unwinding from the pressures of work and everyday life…we’re on vacation!

Bellies full, we embarked once again on our journey, motoring out of town via CT 66 after a quick impromptu detour through a neighborhood to get around some construction backup. We picked up I-691 to I-84 for the rest of the way into New York. Traffic was nice and light on our side of the median at this hour, though we spotted some nasty backups over on the eastbound side between Southbury and Danbury.

By the time we exited onto US 9 in Fishkill, we still had time to spare and I was craving some dessert. Char didn’t take much convincing since we had nowhere to be, so we pulled in to the Red Line Diner for something sweet. To ensure we started this vacation off right, I felt obligated to get an early start on my pie quota. I mean, we could die on the road tomorrow – there is a car tire on the back wheel after all! I ordered a slice of warmed Dutch apple with a scoop of vanilla and a decaf. Char couldn’t resist the thought of carrot cake (her fave), though I think the size of the slice was somewhat alarming.

After a nice late-night break for dessert, we geared up one last time to ride the few remaining miles to our accommodations. Route 9 is mostly a divided four-lane road with cross streets in this section. And wouldn’t you know it, as we entered the Poughkeepsie area, there was a bunch of paving work in progress, with the work crews completely closing off the breaks in the median for making turns, including the left turn onto the street to get to our destination. I had to continue further up a mile or two to do a uey between traffic cones and approach from the opposite direction.

We glided slowly through quiet residential streets south of the City of Poughkeepsie boundary (apparently distinct from the Town of Poughkeepsie which surrounds it). We pulled into the driveway at the indicated address around 9:30 PM.  After reviewing the instructions from our AirBnB host, we made our way around to our private entrance on oddly-placed stepping stones in the lawn, and down to what would be our quarters for the next few days.

It was a cozy basement studio with a big main room containing a bed, TV, small fridge and microwave. To one side was a nice sitting area with a couch, armchair, and loveseat which I felt was a key selling feature since who wants to sit around on a bed in the evenings to relax? Everything was clean and as advertised, though the shower was about the smallest cubbyhole you can imagine squeezing a human body into and still have some elbow room to actually clean oneself. The forced-air ductwork laid across the already low ceiling made for a lot of “ducked walk”. 🦆 🙄

After some discussion about which day-ride routes made sense to do on which days, we agreed on splitting up our weekend into these three main areas. It felt good to settle in to one place, knowing we’d be here for a few days and not have to pack everything up each morning. We’re here!