This is about those times when you see a photo and it doesn’t bring back happy travel memories. This is also about the little towns just up the Hudson River from Manhattan in an area called the Hudson Valley. I’m going to tell you all about the best small towns in the Hudson Valley while also telling the story of a friendship that is no longer.
This is a little different from what I usually write. But I wanted to write it anyway in case it helped anyone else who has felt like this in the past, to know you’re not alone and not all travel memories are necessarily good ones.
If you’ve been reading here for a while, you know that I love to travel solo. It’s my preferred way to travel and I’ve been known to get really anxious when I think about having to travel in any other way. (I have, for the record, traveled successfully with my partner. Thank goodness. But still.) There are occasionally times when I travel with friends and this post is about one of those times.
I was looking through my albums on Facebook while looking for photos from 2011 (not shockingly: I did not find them!) and I came across one called “A Day in Hudson Valley” and although it was a fun day, the memory of driving up there leaves me a little sad.
Back in 2010, I met a guy on OkCupid and pretty quickly after a couple of dates knew I wanted to be just friends. He seemed OK with that and that was the start of nearly a decade of friendship. So, for better or worse, this trip reminds me of that friendship.
I say “for worse” because I ended this friendship almost exactly two years ago. I ended it because it became a one-sided friendship in which I was the only one making an effort so I never felt good after spending time with him. Talking to him was like pulling teeth. I was just tired. In retrospect, I could’ve been more patient with him – probably – because I knew he wasn’t in the most solid place mentally. As Alanis Morrisette once said, “you live, you learn.”
I found this album on Facebook (another reason why Facebook is the best/worst) and I looked at it and I saw my 25-year-old self and my 26-year-old friend and the really poor quality photos that I took with my Canon DSLR that I had no idea how to use and I thought, “That was a fun day.” And then in the next moment, my thought was, “Well, it’s sad that I won’t have any more days with that friend in the future.”
We went up there because he was from a small town in the Hudson Valley and early in our friendship, right before Halloween in 2011, I begged him to go visit Sleepy Hollow with me. We took the train up to his hometown and also went to Tarrytown, Peekskill, and Cold Spring. It was a lot of fun.
Just driving around in the tiny car that he still owned for some reason despite living in New York City, blasting our favorite Weezer and 90’s alternative rock songs. I remember it was during this drive that I first heard the song “Steady As She Goes” by The Raconteurs and it’s been on my favorites playlist ever since.
Hudson Valley Haunts
Sleepy Hollow
Sleepy Hollow felt like an incredibly, for lack of a better word, sleepy little town. Despite the fact that it was almost Halloween, there wasn’t anything going on. We found the famous Headless Horseman Bridge (which isn’t the original one, by the way) and the graveyard where Washington Irving, the writer of The Legend of Sleepy Hollow, and I paid my respects silently. I’ve always loved the movie Sleepy Hollow, which is probably somewhat different from the original story (as most adaptations tend to be), but it’s dear to my heart nonetheless.
The Headless Horseman Bridge in Sleepy Hollow, NY
Washington Irving’s grave in the Sleepy Hollow Cemetery
Some snapshots from the Dutch Reform Church and Cemetery in Sleepy Hollow, NY
Cold Spring
In Cold Spring, a town that I was only familiar with because a woman whose blog I read had moved up there, greeted us with river views and a cool breeze. The main street was filled with antique shops and restaurants and at the end of the small Main Street near the water, we ate classic American food at the Cold Spring Depot with its outdoor seating and people watching as lots of locals going about their days.
25-year-old me 
Cold Spring Depot 
Peekskill
Peekskill, and it’s rustic, cozy Peeksill Coffee House, was and continues to be one of my favorite spots in the Hudson Valley. It’s filled with a ramshackle array of chairs and tables with funny posters on the wall and signs that you might think were bought at yard sales in the 60’s but were probably bought in the last 5 years on Etsy. Prices have gone up over the last ten years, but it’s still more affordable than a SoHo brunch spot or Starbucks. The Peekskill Coffee House is located at 101 South Division Street, Peekskill, NY 10566.
The Peekskill Coffee House
And just around the corner from the Peeksill Coffee House is a tiny, messy used bookshop called the Bruised Apple. Isn’t that the cutest name for a used bookstore? I’ve never bought anything while I’ve been there but anytime I’ve ever found myself within its messy shelves of books, I’ve always felt like this is a place where you could definitely find a first edition of On the Road or a signed version of Catcher in the Rye. The Bruised Apple is located at 923 Central Ave, Peekskill, N.Y. 10566.
This former friend and I had a couple of these kinds of road trips and it always led to days wasted away with coffees and ice cream, walking around these little towns. Sometimes my feelings for the Hudson Valley are a bit tainted because my ex was also from that area and there are way fewer positive memories from that relationship (hence why he’s an ex!). But I always jump at the opportunity to go to one of these towns for a day.
Port Chester
Guster at the Capitol Theatre in 2013
Around this time last year, Nick asked me if I’d go with him to a Dark Star Orchestra concert with him in Port Chester, another little town along the Hudson, at the Capitol Theatre. In 2013, I saw one of my favorite bands, Guster, there, so I was familiar with the venue as well as with Port Chester. I remembered there was a little hole-in-the-wall greasy spoon near the venue that served the best chili called Hubba. Hubba is located at 24 Main St, Port Chester, NY 10918.
Chili Cheese Fries from Hubba in Port Chester, NY
Nick and I didn’t go there this time (they don’t make vegetarian chili afterall) but I did remember the way from the train station (warning: you have to walk up a hill) to the venue and all the little bars and eateries along the same main street. We ended up at a little Mexican-American restaurant called El Tio where you could smell the fresh tortillas coming off the grill and the baskets of tortilla chips never dried up. Main Street has a few nice restaurants but it’s also filled with numerous dive bars that are packed before and after concerts at the Capitol Theatre. El Tio is located at 143 Westchester Ave, Port Chester, NY 10573.
The Capitol Theatre is located at 149 Westchester Avenue, Port Chester, NY 10573.
Tarrytown
We had tickets to go see Guster earlier this month at the Tarrytown Music Hall in Tarrytown, but as you can probably guess, it was canceled and will hopefully be rescheduled at some point. Tarrytown is one of the Hudson Valley towns that I’m less familiar with but, like Port Chester and Cold Spring Harbor, it also has an adorable Main Street shopping and dining area.
A couple of photos from the 2011 roadtrip.
There are historical site markers all around these Hudson Valley towns.
I found some photos from the aforementioned day trip in 2011 and in the background of this photo of the Coffee Labs Roasters, you can see the marquee for the Tarrytown Music Hall. The Coffee Labs Roasters is another adorably cozy coffeehouse, similar to the one in Peekskill. Coffee Labs Roasters is located at 7 Main St, Tarrytown, NY 10591.
Coffee Labs Roasters & Tarrytown Music Hall’s marquee just behind it.
The Tarrytown Music Hall is located at 13 Main St, Tarrytown, NY 10591.
Friendships & Traveling
Even though the friendship that introduced me to the Hudson Valley is no more, it’s getting easier to see these photos and think of them as good memories as they, and the friendship, become more distant. I’m also glad to be replacing these somewhat sad memories with newer, happier ones as the years go by.
I am truly thankful that this person came into my life when he did and had a hand in introducing me to these little Hudson Valley gems. Otherwise, I’m not sure when I would have ever made the effort to leave New York City for a day to explore the area to the north.
Not every friendship is meant to last forever, I know that. But travel memories do last and I’m grateful for that because even if the memories are sad at first, I’m glad I went to these places with these exact people because everything’s meant to happen for a reason in exactly the way it happens.
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