When I told Sal I was moving to Rhode Island, he was pretty bummed. In the four years prior, we’d set a pretty good cadence for bike tours around New York City and the surrounding area, but with me no longer living there, coordinating trips was about to get a lot harder.

A few months before the move, I got an idea: I had to get my bike to Rhode Island somehow… why not do it with me on it? I ran it by Sal, and it didn’t take long to get him on board. That spring we started to put the plan together, according to our usual roles. I mapped out the route, while Sal researched options for meals and made the arrangements for places to sleep via Warmshowers.

What follows is the daily ride reports I posted on Strava. I also created a highlight of my Stories from the trip on Instagram.

Day 1: Brooklyn to White Plains

Note: The first two miles of the trip were logged separately, but my GPS glitched out.

Not many other riders out on a weekday evening. Mostly CitiBikes on the Hudson River Greenway, plus a few hot-doggers here and there. A couple asshole motorists in northern Manhattan and the Bronx, which wasn’t surprising at all.

It was my first time on the 2-way bike path that follows Broadway around Van Cortlandt Park. It’s probably better than nothing, but it’s bumpy and interacts with highway onramps awkwardly. They need to just pave the rail trail through the park already.

Once we got to Yonkers we hopped on the South County Rail Trail, and oh man was it dark. There’s a reason that trail closes at dusk. Thankfully we brought headlamps. The Bronx River Parkway path was similarly dark, but at least interacted more with roads and towns along the way, so it wasn’t just one long creepy ride through the forest. At one point the path ducked under a bridge, and we had to crouch down to get under it. The river was so high it almost flooded the path. Pretty cool, but too dark to photograph.

From Scarsdale to White Plains: Suburbs, suburbs and more suburbs. Quiet neighborhoods with desolate streets and obnoxiously large houses. Seriously, what do people do with all that space?

On to Danbury tomorrow.

Day 2: White Plains to Danbury

We started out from Sal’s parents’ house and immediately climbed a big hill. We passed a tree cutting crew and one of the workers said “boy I wish I was you guys”, and we both said “not at the moment you don’t!” That turned out to be the first hill climb of many.

After a quick breakfast we headed west though White Plains on some questionably bikeable roads, until we got to Elmsford and the Westchester/Putnam County Rail Trail. Oh man, that trail is great. We spent nearly the whole day on it.

The best part about rail trails is that trains aren’t great at climbing hills, so when the railroads were built they went to great lengths to keep the inclines gradual. That means that any rail trail you ride is going have nice, gentle climbs instead of steep hills. Not that there aren’t hills, of course.

We stopped in Yorktown Heights for lunch, at a Himalayan place in a strip mall that was really delicious. We probably ate too much, though, because the next 7 miles of the rail trail were all uphill, and digesting lots of heavy food while pushing uphill is a bad combination. But the rest of the trail from Mahopac on was nearly all downhill, and that was exhilarating.

The trail ended in Brewster and we were sad to leave it. A quick stop for coffee and a bathroom break revealed Brewster to be… kind of a sad town. We chatted with an old man on the street who was excited to tell us how much cycling he’s going to do “in the next life.” Nice guy though.

Remember when I said we climbed a lot of hills? The bulk of those were over the last 5 miles, and they were rough. But we made it to our first Warmshowers in the hills north of Danbury before sunset, and our host has offered us enchiladas and wine. Life is pretty good.

Tomorrow will be all street riding, but we’re aiming for mostly the small, quiet country kind of road, which unfortunately means more hills. Meriden is our destination, which puts us close to the Connecticut River and past our overall halfway point.

Day 3: Danbury to Meriden

When I told my dad about this trip, he said it was too bad we were going west to east across Connecticut, because all the hills run south to north. Meaning we would have to go over them all. That’s what most of today was about.

After sitting for coffee with our first Warmshowers hosts Matt and Jill (and petting their dogs) we set out down the steep hill from their house to Danbury proper. We stopped for breakfast at a nice bakery downtown called Mothership, perhaps dawdling there longer than we should have, but the breakfast burritos were tasty.

East of Danbury we hit our first set of hills, which were tough but rewarded us with a great view across the next valley. There was a nice lookout with a bench, but I forgot to take a picture there. I was already getting tired at that point, as the extent of the trip was starting to take its toll.

On the hill down to Newtown (home of Sandy Hook Elementary) there was a sticker on a sign that said “WE ARE NEWTOWN AND WE CHOOSE FREEDOM.” So… there’s that.

Our other reward for our first climb was the road down past Rocky Glen state park, which was pretty and all downhill to the Housatonic River. South of the bridge over the river we could see the remains of what I assumed to be an old railroad bridge, signaling to me that there’s another rail trail waiting to be built in Western Connecticut.

The second chunk of hill, between Southbury and Middlebury, really kicked our butts. Not much else to say about that except I think it may be another day or two before our metabolisms catch up to the amount of calories we’re burning.

At Middlebury we found another nice rail trail, freshly paved but shorter than we’d like. We stopped for lunch at a pizza place right off the trail, on the site of a former station according to the sign.

After that we opted to go through Waterbury, which was a mistake. Waterbury quickly surpassed Brewster as the most depressing town we’ve passed through so far. That was followed by our third chunk of hill for the day, and by that point we were exhausted but resigned to our fate, so the climb was tough but unmemorable, save for that it culminated in a 10% grade back down the other side, which was a blast. (The sign warning of it was the only still picture I got, but there are plenty of videos on my Instagram story.)

On the last part of our journey to Meriden, we managed to catch a small piece of the Farmington Canal Heritage Trail, which was beautiful, and brand new according to our second Warmshowers host, Carol. She fed us dinner and offered us lots of interesting conversation about bike touring and national parks.

Tomorrow is our longest push of the trip at 55 miles, and is supposed to be the hottest day of the weekend. It should be interesting.

Day 4: Meriden to Canterbury

Our longest day so far at nearly 60 miles. We set out from Meriden after coffee and a garden tour with our host Carol, who is a wonderful human. We opted to ride for a while before breakfast, and we ended up covering the first dozen miles or so on nothing but caffeine, CLIF bars and trail mix. I wouldn’t necessarily recommend that approach, but it did help us move faster because we wanted to eat.

We crossed the Connecticut River at the Arragoni Bridge in Middletown. It has nice wide paths on either side that no one seems to know about or use. When planning this trip I did some research to see if the bridge was passable, and I found an op-ed in a local newspaper where the author asked his audience if anyone was even aware that you could in fact bike over it. You certainly can, and we did.

We stopped for breakfast/lunch in Portland at a little breakfast spot Sarah’s on Main, with a super nice staff who ended up being the first people on the ride (other than our Warmshowers hosts) that we actually told what we were doing. They were surprised, but sort of nonchalant about it. nbd.

Then we left Portland via CT-66, which is a divided highway for a bit and not very bike friendly. But it wasn’t long before we caught the newest section of the Air Line Rail Trail, which we found almost by accident when we passed a side street and Sal said, “hey, I think I saw a bike trail crossing sign back there, should we go check it out?”

The Air Line trail is awesome. It runs all the way from Portland to Willimantic (with the exception of a small unfinished section between Portland and East Hampton, which we found out the hard way and had to double back a bit). Overall I think we were on the trail for over 25 miles, which was nearly half our ride for the day. As with other rail trails, it was designed to be as flat as possible, so we barely felt any changes in elevation along the whole stretch. The only small drawback was that it’s gravel instead of pavement, but I kept saying “flat gravel is better than paved hills,” and Sal agreed.

We also met a bunch of really nice people along the trail who were curious about our gear and where we were going. Again, no one really cared to ask us about our trip for the first 3 days, but today on the Air Line everyone was out and super chatty. There was a group of cyclists in East Hampton, a dad and his son from Brooklyn who had come up to go bikepacking, and a retired couple on folding bikes who tour rail trails around the country. All super nice people, all out to enjoy the Air Line for the day. Bike tourism is real and awesome.

When we got to Willimantic we decided we needed to eat dinner before we finished out the day, so we stopped at the Willimantic Brewing Company for a burger and a pint each, which were tasty in all regards. We knew it meant we’d be riding after dark, but we needed the calories. And oh man, did we.

The last 12 miles of the day were along CT-14 between Willimantic and Canterbury, and they were brutal. We climbed hill after hill after hill, each taller and steeper than the last. The elevation map looked like shark’s teeth. But we took our time, and had our blinking lights and headlamps on, as well as our Safety Pizzas. And we made it without incident.

Side-note: I have to say, I’m super impressed at how nice Connecticut drivers have been to us. Every car that passed us tonight—on a dark road with no street lights and a 45MPH speed limit—slowed down on their approach, made sure no cars were coming the other way, and then crossed the rumble-stripped double-yellow lines to pass us. I was blown away by their conscientiousness.

Tomorrow is our last day! Almost 200 miles down, 40ish to go. Providence or bust.

Day 5: Canterbury to Providence

Ocean State in view! O! The joy!

Our last Warmshowers hosts made us breakfast, and we ate it with them on their patio. They live in a really nice 180-year-old house in the middle of a lovely chunk of Connecticut countryside. The dad and son each had a test ride on Sal’s trike (it turned out to be too strange for them) and then we pushed off.

As usual, the previous night’s uphill climb was rewarded with a long coast downhill. We stopped in Plainfield for a snack and a coffee, which detoured is a bit. But we needed the extra energy, because just east of Plainfield we’re the last two big Connecticut hills of our trip.

Now, I will readily admit that all my talk of “big hills” on this trip has been subjective; we aren’t in the Rockies or the Alps, we’re in New England. But when you live and ride along the coast, and the biggest climbs you usually deal with are the East River bridges, a series of 300ft climbs on your fourth or fifth day in a row of riding seem anything but small.

Anyway we took our time, and before long we were zeroing in on the Rhode Island border. (Side-note: This is the border that I often refer to as the CT/RI DMZ because it’s so rural, but that made for some beautiful scenery.)

I’ve been telling people for days that this last stretch would be the easiest, because the Trestle Trail/Coventry Greenway/Washington Secondary Trail would take us most of the way across the straight, and it was all downhill. The trail was indeed spectacular, and I plan on spending a lot more time on it in the future. And coasting down its 20+ miles made for a very quick ride.

But! The trail ends abruptly just south of the Cranston/Providence line, which meant zig-zagging through Silver Lake and Olneyville for a while. I suspect it wouldn’t be very difficult to complete the trail into Olneyville, where it could connect to the Woonasquatucket River Greenway towards downtown. I’ll add that to my growing list of projects to advocate for along the route of this trip. (Extending the Trestle Trail west to Moosup is another.)

We did eventually find the Woonasquatucket Greenway, but it was a bit disjointed and sadly too brief to be very useful to us. But the river itself was very nice in the parts we went by.

By the last stretch, we were tired and hungry and moving very slowly. We crawled up Pleasant Valley Parkway to my sister’s neighborhood, and when we got to her place she had a crowd of people outside cheering us on and congratulating us. It so happened that she was having a cookout this afternoon, and her guests—many of whom are mutual friends of ours who I’ve known for decades—knew we’d be arriving, so they waited outside for us to arrive. It was an overwhelmingly nice gesture, and a great way to end the journey.

And that’s it! I’m tired. I’m sore. My knees hurt. My head is still spinning trying to grapple with what we’ve just done. It was pretty crazy. But we did it!

I am endlessly grateful to my touring partner Sal, for being crazy enough to join in these rides, and for taking on the logistics of eating and sleeping that are more that I can deal with sometimes (usually), and for being patient and selfless and generally up for anything all the time.

Total miles: 236
Total climb: 11,000ft
Rain: None
Flats: None
Crashes: None (though I did fall over once)