Empire State Trail: Albany to Lower Manhattan (230 miles)

My cousin and I decided to make this year's bike trip a jaunt from Albany to New York City on the (relatively) new Empire State Trail.  This is the summary of the trip that I submitted to Adventure Cycling Magazine:

Two grown men looking for something on a trail with bikes, struggling to find it.

Why do we travel?  If you look at it logically the best explanation is to "see things you can't see at home", "experience a culture you can't experience at home" or "eat things you can't eat at home (or at least they aren't nearly as good at home)".  These make sense as a starting point but they aren't a full explanation.

Moving a level deeper, do we travel for adventure?  I think some of us do, and adventure is very much defined by an individual.  Do we travel to bond with others?  I think that can be part of it.  Do we travel to get out of our own heads and get into a healthier frame of mind?  

I'm not what you would call an experienced bike traveler, but I'm not a novice either. This is my first travel article!  I've done the GAP and the C&O along with the Virginia Creeper, the Pinellas trail and Elroy-Sparta.  I've done most of the Katy. So I've hit a lot of the high profile US trails.  This May my cousin and I took on the southern portion of the Empire State trail (Albany to New York City).

My cousin and I are not what you would call close.  We are trying to build a relationship, but as many of you know it's very difficult to make up for lost time. I'm originally from Massachusetts, I moved out to Chicago in 2005. I'm turning 50 this year, my cousin is 40.  He lost his younger brother to an over dose in 2019.  I wish I could sit here and say this affected me, but I was not close with his brother either.  Perhaps, in retrospect, it was not the greatest idea to spend six days biking with someone you barely see once a year but we gave it a shot. It wasn't a disaster by any means, but it also wasn't a rousing success either.

Two grown men reaching for something on a trail with bikes.  One of them firmly in middle age and struggling.

When you travel you have the travelers you know.  Mostly the people, but it's also the bikes and occasionally an animal depending on what you are doing.  You also have the entities you don't know are there...the doubt (sometimes self, sometimes in others), you have the travel styles and in our case you have the anxiety. 

Enough with the depressing side of things!  The good news is that The Empire State Trail is fucking awesome!  I loved the ride and I'll do my best to communicate to you, SPECIAL READER, that it's a trail as good as the others I detailed above.  

Trip Status:  We start this one at Defcon 4, just because of the camping uncertainty and the general unease and family dynamics.

Day 1:  Albany to Germantown (54.5 miles with 2,452 feet of elevation gain)

I generally break up these types of trips to about 50 miles a day. I am divorced with a four year old, so I don't have time to train like I used to.  However I'm still in good enough shape that I can get on a bike and do 50 miles with minimal training.  I can't run a fucking mile (I hate running and I'm not build for it -- too tall) but I can bike plenty.

The trip really started the night before. I mentioned travel styles earlier and my travel style, particularly when it comes to biking, is to wing it a bit.  I don't think the Empire State Trail has the traffic that it will in 5, 10 or 20 years. Particularly not in May, so I only booked one night in advance (Tarrytown, outside of NYC). I wanted to book NY City in advance but the prices were so ridiculous (600 dollars a night is what I remember) that I didn't bother.  This IS NOT my cousin's preferred style, something that became apparent over the week. 

I was driving from Chicago so I got in on the later side (around 5). We were planning on camping in a forest near the trail so we would have a place to stay both on Sunday and Monday but it became apparent that we didn't really have the equipment for the overnight temperature drop and it was going to be a lot of work to find a decent camp site, so we pivoted over to looking for a hotel.  We found some cabins a few miles off of the trail.

Now seems like a good time to talk about the general zeitgeist of upstate NY. Upstate NY is a beautiful place but the people are a little rough around the edges. I don't mind this, I grew up in the Massachusetts suburbs in the 80s so I'm used to it. Hell, I'm a little rough around the edges, but the woman who rented us the cabins was a FIRST CLASS asshole. I get the feeling there might be a few more of these types squirming around the Hudson valley.  Anyway, there are plenty of ASSHOLES everywhere, you can't let them get you down.  She turned out to be ok, but the cabins were expensive and not all that nice.  I do believe the demand for travel in that area has skyrocketed over the past few years, probably COVID related, so if you do decide to bike up there keep that in mind, especially during peak season.

We finally got on the road the next morning in Albany.  Now is a good time to note that you can park for something around 10 dollars a day in the Renssaler Amtrak station lot. It's maybe a half mile from the trail and is pretty secure.  We didn't spend any time in Albany, I'll leave that for a future trip. I (we?) plan to tackle the Buffalo to Albany section of the trail in two separate trips over the next two summers.  Syracuse to Albany with a finishing stop in Saratoga for the races in 2023 and Syracuse to Buffalo for a Bills game in 2024.

The signage for the trail is excellent, some of the best I've ever seen, but it needs to be because while most of this segment of the trail is on path, not all of it is.  This includes the first few miles out of Albany. There is also a ton of elevation gain on this trail, more than I've ever done and that includes the first 30 miles out of Cumberland on the GAP trail, which is about 25 miles of climbing.  For future reference, I didn't have to walk my bike at all on the GAP.

The first day was long but it was manageable up until we got to Hudson.  That's somewhere just short of the 40 mile mark.  We got into Hudson thinking we were ok and just had to finish up the last 12 or so miles to Germantown.  

An aside here:  I looked at the elevation charts but evidently I don't know how to read elevation charts worth shit because I had no idea what was coming.  As I said before, I didn't train a ton for this...but I don't think it would have mattered much. The next...I don't even know how long it was...three hours?  During this time I got my ass kicked worse than any other athletic endeavor that I can remember.  This includes my 10 years training various forms of combat sports.  I pride myself on not walking my bike...that went right out the window.  I lost count of how many hills I had to walk it up at 12.  That spiraled into me realizing that I was now one of those people I looked down upon..."Oh, look at that poor person walking their bike...hahaha!"  So not only was I humbled by that but my internal Massachusetts voice took over and started the degrading "Ohhh, look at me! Big BIKE RIDER MAN has to WALK HIS BIKE like a FUCKING PUSSY!" (Sorry, the voice inside my head is stuck in the 80s, which is to say it's not very PC)  Numerous other self-insults were streaming during these trying times.  

Massachusetts is a funny place. I feel like the editor of this magazine, a fellow MASSHOLE, will relate.  I love the fact that I'm from there because it's a place that truly values education and particularly education in the form of critical thought.  But, at least where and when I grew up in the 80s, it was emotionally brutal.  Whatever weakness you had was pointed out early and often to the point you you will never forget it, even if you motivate and eventually turn that weakness into a strength.  Some of this translates into humor and Massachusetts punches way above it's weight when it comes to comedy.  Some of it translates into persistent self loathing. 

Anyway, this is a roundabout way of saying that the stretch between Hudson and Germantown was the most difficult biking I've faced and I was both humiliated and humbled by the experience.  I would do it again but I would not enjoy it. 

When we got into Germantown we no longer cared how much money it cost to stay there. Germantown is a small enclave right on the trail.  It feels like a bunch of people from a Brooklyn neighborhood got tired of paying Brooklyn prices and up and moved 150 miles north and did their best to create a Brooklyn neighborhood in a rural setting.  We stayed at a fancy B&B Central House, which was more than we wanted to pay but at least we were the only people there. We literally had the run of the place. There was an expensive restaurant across the street called Gaskins. Again, beggars can't be choosers. We had a meal there and then got some more food at the Otto's Market.  Otto's was fantastic, if a little pricey, but we got breakfast there that morning on the way out of town, some extra food after dinner and breakfast again on day 2.  Sometimes not having a choice is preferrable. 

Trip Status:  We were holding at a DEFCON 4 until that last 12 miles, which pushed us to a DEFCON 3. 

Day 2:  Germantown to New Paltz (41 miles with 1,559 feet of elevation gain)

At the onset of day two we were making contingency plans in the event we couldn't finish the trip. We had no idea if the 12 miles south of Germantown were going to be as difficult as the 12 miles north of it were.  The first few miles were decent and led us to one of the highlights of the trip, which was a church in Tivoli.  We stopped and admired it for a bit. Neither one of us is particularly religious but we can appreciate good architecture.  

We were fortunate that there was only one spot where bike walking was required. It was on this path just outside of the campus of Bard college in Annandale-On-Hudson.  The rest of the day was manageable. We had planned to stay in Poughkeepsie but when we rolled into New Paltz we decided that was as far as we wanted to go.

Both days I looked at the Empire State Trail website for the elevation. All four days looked the same to me, like I said maybe I need someone to teach me how to read it or <take another look for the second draft>.  I pride myself in being competent in such tasks, so this one stung a bit. 

Now before I said that I am more of a wing it travel guy when it comes to these types of trips. That was probably a bit of a negative on day one but I think I'm giving myself points for the flexibility on day two. Another travel issue that I feel is on people's minds but is rarely discussed is the economic situation of all parties.  I am older and I make more money than my cousin. I've been on both sides of the economic gap when traveling and I take the stance that it's up to the person in a better financial position to compromise and travel a level down compared to what they are used to.  I did my best in this case, plus I think these types of trips are more fun when you operate on a smaller budget.  

New Paltz is remnant of the hippie commune era of upstate New York. One of my favorite authors is from Cooperstown (Lauren Groff) and she wrote a book called Arcadia that dove into that culture.  

We explored staying at a hostel but ended up at a Hampton Inn just outside of town.  At this point the cracks in the relationship were just starting to emerge, but nothing too difficult. We weathered the 12 MILES OF HELL the day before and we were only slightly off schedule.  

Trip Status:  Back to Defcon 4

Day 3:  New Paltz to Brewster (56 miles with 1,422 feet of elevation gain)

They day started with a 15 mile downhill run from New Paltz to Poughkeepsie. We really needed this as it put us back on schedule.  However I did notice that I had popped a spoke on my rear tire somewhere on that descent and that had me concerned.  I'm not an expert with those types of issues, so I wasn't sure how long I could ride on it.  

Riding into Poughkeepsie there a pedestrian bridge called "Walkway Over the Hudson". I don't know if this is the crown jewel of the trail but I can't imagine anything more impressive. If you told me this was the nicest bridge of it's type in the US I would believe you.  

The city of Poughkeepsie...not so much.  I tried finding a bike shop there and while we did find a place the owner couldn't fix my problem.  Poughkeepsie not horrible by any stretch but it also clearly was not thriving.  We took our chances and kept on moving forward.  A lot of the day was downhill so it was pretty easy, even with the broken spoke. The rear tire didn't get any worse so I ended up on it for the entire day.

We were back on schedule and got into Brewster and decided that was were we were going to stay. This is where me made our first of two tactical errors of the trip.  My cousin booked a cheap hotel a few miles off of the path. This was six miles of difficult hills after a day of riding, with angry traffic.  I didn't say anything but I'm sure my cousin could pick up on my frustration on doing this to save what amounted to 20 dollars each.  

This is when things started to sour a bit for me as I could pick up on my cousin's general displeasure and anxiety. Since I "planned" the trip and was older I felt like every problem was "my fault" and that started to weigh on me a bit. This is probably true to an extent, I'm the one who introduced him to the concept of these long haul trips and I have more experience. He also muttered a couple of things under his breath that I caught.  Little things, not even worth explaining here but they hint at unresolved child hood resentment. Mine as well cover that now.

This side of my family, my Father's side, is the side I spent more time with growing up. The family is based in western Massachusetts and very male dominated.  My Father was one of seven.  Out of the seven, five had a total of eleven kids, of which eight were boys. It's a male dominated family and there was definitely a culture of the older kids "toughening up" (or hazing or brutalizing) the next generation.  When I was growing up I was in the cross hairs of my Uncle (cousin's father) and an older cousin. Part of the hazing was physical (acorns hurls at you at high speeds, charlie horse's and horse bites), part of it was psychological.  Violence, in any form, begets violence.  I hazed my cousin and his now deceased brother.  A couple of years ago in the middle of Thanksgiving dinner my deceased cousin decided to air many of these grievances.  I ate it, as that is clearly what I should have done and didn't really have a choice. I'm not proud of it and I'm not above apologizing for it but I don't know how to go about it in a sincere manner considering how much time has passed.  Also, my cousin's were the youngest of the eleven and therefore there was no one below them to place their aggressions.  

Honestly, we could probably benefit from some family counseling to facilitate an apology on my end.  But, I would not even want an apology from my Uncle and other cousin at this point.  I believe that, at some point, you have to make peace with whatever happened in your life (trauma, failure, success) and move forward. 

I'm also a little passive aggressive in these situations, we both come from a German Irish family so we drink and make jokes but we don't necessarily communicate well or SHARE OUR FEELINGS. Or maybe I'm just an over analytical douche who lacks self confidence and I'm projecting all of this shit.

Anyway, all's well that ends well.  We went to a fancy place for dinner that was just down the street from the flea bag motel we stayed at.  Two grown men trying to navigate through the funhouse of life, not sure what they are seeing in the mirrors.

Trip Status:  Despite the annoyances I think we more or less held at DEFCON 3.  I think at this point we had run out of conversation topics, which is to be expected. 

Day 4: Brewster to Tarrytown (49 miles with 1,954 feet of elevation gain)

The day started ok and finished ok.  We got a pretty good gas station breakfast in Brewster.  

One good thing I did for myself on this trip was learn how to eat properly. In the past I would go on these trips and think because I was exercising I could eat whatever I wanted. That, like most things diet related, is rooted in denial.  I've been trying to lower my cholesterol by cutting way down on dairy and saturated fat and I was able to mostly stick to that.  This carried over to after the trip and I'm down about 10 lbs from pre-trip and, most importantly, it feels sustainable. Donuts ARE great but I feel a whole lot better when I live in moderation. 

I still had that blown spoke and we came across an EXCELLENT bike shop called Bikeaway.  It's a local chain with a few shops in the area.   They were able to fix my spoke well enough so it held out for the remainder of the trip.  (I ended up getting a new wheel shortly afterward because I was sick of spokes popping off) 

The guys at the bike shop recommended stopping at the Crotton Dam, which was definitely worth the detour.  But if I had to do it again I would have looked closer at the routes parallel to the Empire State Trail as we really fucked up getting from the Dam to Tarrytown.  We were on road with trucks in roads that were not friendly to bikers.  The whole experience was stressful.  In fact, I violated one of my cardinal rules: DON'T LEAVE THE FUCKING TRAIL.  

We got through it but it wasn't fun.  We ended up in Tarrytown in Westchester county, which I really liked a lot. Had a great meal (aren't they all great when you are hungry from riding?) at this place over looking the new Tappan-Zee bridge. I refuse to call it the Cuomo bridge or whatever.  That guy can suck it, clearly a shit heel if he felt the need to name that bridge after himself.  

Trip Status:  Holding at DEFCON 3.  Fortunately we were both raised by similar people so we know how to project resentment right up until, but not crossing, the line.  I honestly can't remember exactly which night but I think it was in Tarrytown where we exchanged our knowledge of the family skeletons.  That's always good for some bonding and a few laughs. 

Honestly, most of the trip stress for the 240 miles was pretty normal but for whatever reason our sense of humors didn't or don't quite line up.  So we never had the release part of the tension and release that needs to ebb and flow in any situation.  

Day 5: Tarrytown to Lower Manhattan (40 miles with 715 feet of elevation gain)

This was a pretty easy day all around.  We got ourselves going and came across some of the random fun things that make bike travel great.  The trail goes through Sleepy Hollow so we saw the graveyard where Washington Irving, the author of the Headless Horseman, is buried. At one point we passed through a series of decretive bird houses. NY City is full of history and as we entered into the Bronx from Yonkers we stopped to see some granite pillars representative of one of the building booms in the early 20th century. 

The trail throws you into Manhattan out by Columbia University. You are on the streets for a bit and then you end up on the Hudson river and that is the final stretch. The end of the ride was pleasant but anti-climactic.  I'm from Boston, but moved to Chicago in 2005 because I wanted a bigger city. Most people from Boson, when they want that kind of change, go to NY City.  I like NY City, I appreciate it  but, for whatever reason, it doesn't excite me like it does a lot of people. This was a reminder of that.  Plus the Yankees play there and they eat shit.

I had not been to NY for eleven years so it was interesting to see some of the changes (New World Trade center, "Super Tall" sky scrapers) but it also confirmed that NY has lost some of it's edge.  We went to comedy on MacDougal street and it was...very average. Now we weren't at the Comedy Cellar, but we were only a couple of doors down.  Anyway, I digress.  My cousin had not been to NY as an adult so we got a pretty good taste of it. Walked through Central Park, got dinner at one of David Chang's Momofuku restaurant's. You could live in NY for decades and never see all of it, but my cousin got a pretty good tour considering we were there for less than 24 hours.

Travel Status:   Holding at DEFCON 3.  The stress mostly stabilized.  I think we both wanted to be off of our bikes at that point.  

Total:  240 miles with 8,102 feet of elevation gain

Conclusion:  The Empire State Trail is WORLD CLASS, or maybe a better description is that it's on it's way to WORLD CLASS.  It's every bit as good as the other top trails in the US.  It will be nice when there is more biking infrastructure build up around it like they have on the Katy, Gap and C&O. Trail towns and bike cabins and the like.  The Albany to NY stretch is manageable with the exception of the Hudson to Germantown piece.  

For any of the entrepreneurial folks in the Hudson Valley area I feel like there are a lot of opportunities around the trail for lodging options specific to bikers.  I also feel like there is an opportunity for some kind of creative e-bike rental to get you between Hudson and Germantown. Did I mention that 12 mile stretch sucked? 

As far as my cousin and I there was never any real drama. There was never a "Fuck You" moment, at least not an obvious one. But at the end of the trip I think we felt more distant, or at least the same, as before it started. It didn't bring us any closer and that is not what we had hoped. 

Now I think it would have been a lot easier if we had another person, like one of our friends or my brother.  We both tried that but given middle aged responsibilities and schedules it's difficult to line things like that up. 

There's just no making up for lost time but, if you need to get an answer to that question, you mine as well find it while you are biking in one of the most beautiful areas on one of the best bike paths in the US. 

Final Travel Status:  I'm going to leave it a DEFCON 3.  The good bye was a little awkward and we haven't spoken since (It's September) but I hold out hope that we can do this again next year with another person or two involved and a shorter trip (2-3 days and not 6)